Comeback Players

In early June 2018, Seattle Mariners backup catcher Chris Herrmann was almost ready for the rehab assignment that would complete his recovery from a strained oblique. Before he could get into games, though, Herrmann had to perform “baseball activities,” one of which was to take batting practice. There was one problem: He had no batting practice pitcher.

Herrmann was in Seattle, while the Mariners and their two local minor league affiliates were on road trips. The personal trainer who normally would have thrown BP for a rehabbing player had flown home to tend to a family emergency, and the assistant strength and conditioning coach who remained had no baseball background. If a pitcher couldn’t be found, Herrmann would have had to fly to and from a more distant affiliate or wait for the major league team to return to town. Either option would have delayed his comeback. For want of a BP pitcher, a backup catcher would have been lost. And for want of a backup catcher … well, this was the Mariners, so the season was likely to be lost one way or another. But despite being mired in a decades-long playoff drought, the team was in first place at the time, and having Herrmann would help.

Fortunately, a solution presented itself—or, rather, himself. “I said, ‘I’ll come down; I’ll throw him BP,’” Jerry Dipoto recalls.

Dipoto, then the team’s general manager and now its president of baseball operations, is a former major league reliever, so tossing fat pitches for Herrmann to tee off on for 20 to 25 minutes was well within the then-50-year-old righty’s skill set. After the session was over, Dipoto remembers, “I gave him a little fist bump, and he said, ‘That was pretty good. … Did you play in college?’ And I said, ‘Yeah, I did.’ And he said, ‘That was pretty impressive.’” Herrmann then approached the strength coach and said, “When have you ever seen a GM who can throw BP like that?” The coach said, “You know he pitched in the big leagues, right?” To which Herrmann responded, “My God, I feel like an idiot.”

“Of all people, man—the GM,” Herrmann says five-plus years later, with a wince and a laugh. “I’m like, aww, gosh, maybe I should’ve done my homework on this guy.”

Herrmann needn’t have been so hard on himself. (Who hasn’t embarrassed themselves in front of their boss?) He’d joined the Mariners less than two months earlier. Plus, Dipoto wasn’t a star player, and he hadn’t pitched in the majors since 2000, when Herrmann was 12 years old. Beyond that, though, Herrmann was right: There really weren’t many GMs who could throw BP like that. In 2018, only two former major leaguers were running baseball operations departments, and Dipoto was the lone former pitcher. The backup catcher may not have been familiar with Dipoto’s past, but his surprise reflected the reality of the era: Ex-player GMs had never been more scarce.

Ever since the development of dedicated general managers a century or so ago—in contrast to the field managers and team owners and/or presidents who typically put teams together before then—there has always been a mix of top executives from nonplaying and playing backgrounds: the figurative descendants of Ed Barrow and Branch Rickey. Though the numbers in each category waxed or waned from year to year, near balance was mostly maintained. In the second half of the 20th century, roughly 43 percent of GMs in the average season had previously played professional baseball, and approximately 27 percent had made the majors.

This century brought a new model of a modern majors general manager: one who couldn’t serve as a substitute BP pitcher, even in a pinch. Post-Moneyball, MLB C-suites have been more hospitable to people who dominated fantasy sports than to former professional athletes. As Ringer contributor Noah Gittell puts it in his forthcoming book about baseball movies, “Sabermetrics shifted the power from those who played the game (players and managers) to people with economics degrees who had never set foot on a major league ballfield. These new baseball gods were young and smart and probably not very good at playing baseball.”

Those new gods aren’t going anywhere, but after bowing before them for almost 20 years, the league seems to be embracing a blend of the old gods and the new while filling front-office leadership roles. White Sox assistant GM Josh Barfield says an apparent resurgence in teams’ interest is “definitely something that I’ve noticed and that we as former players talk about, because you used to see that a lot more when a lot of us were coming up, and then the pendulum swung.” Now, he asserts, “We’re seeing it come back the other way.”

That doesn’t mean many GMs will be called upon in batting practice. But you know who could throw great BP—and who, at 6-foot-10, wouldn’t surprise many hitters when he revealed his baseball background? Texas Rangers GM Chris Young, who last year became the first former big leaguer to run the baseball operations of a World Series winner since Kenny Williams of the White Sox in 2005. Another new emergency BP candidate: Craig Breslow, the first-year chief baseball officer of the Boston Red Sox, who, like Young, last stepped off a major league mound in 2017. In 2024, those two, along with new White Sox GM Chris Getz and Dipoto, constitute double 2018’s total of MLB alumni at the top of baseball ops org charts. Several other ex-MLBers—some of them hotter prospects as execs than they ever were as players—are one or two title bumps away from joining them, including Dodgers GM Brandon Gomes and Phillies GM Sam Fuld (the seconds-in-command to POBOs Andrew Friedman and Dave Dombrowski, respectively), and four assistant GMs: Barfield, Randy Flores (Cardinals), Jorge Velandia (Phillies), and Gabe Kapler (Marlins).

In 2011, Jayson Stark wrote for ESPN, “These days, you almost never see a team trot a former player up to the podium to try on his general-manager hat.” Nothing changed for the rest of that decade: Throughout the 2010s, teams tapped only two new former players, Dipoto and Tony La Russa, to be baseball ops top dogs. (While overseeing the Diamondbacks’ baseball operations as the team’s chief baseball officer in 2014, La Russa also appointed erstwhile A’s ace Dave “Smoke” Stewart—Herrmann’s former agent—as GM, though Herrmann never faced Stewart’s batting practice smoke when the catcher played for Arizona in 2016.) But between Breslow and Getz, the league has added that not-so-grand total just in the past several months. And for the first time in ages, there may be more in-demand ex-player GM candidates than there are GM job openings: Before Breslow got his gig, Gomes, Fuld, and Kapler either interviewed for the Boston job or declined invitations.

“What I’m impressed with hearing them is that when you talk to them, you don’t necessarily say, ‘Oh, wow. These guys are ex-players,’” says A’s senior adviser Billy Beane. “You say, ‘Wow, these guys are really bright guys.’”

It’s about time teams rediscovered that it’s possible to be both.

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Among current team decision-makers, Dombrowski is uniquely capable of taking the long view (even though he’s known for making win-now moves). The 67-year-old Phillies POBO broke into baseball with the White Sox the year before Disco Demolition Night. En route to becoming the game’s youngest GM in 1988, he apprenticed under execs who hailed from opposite ends of the playing-experience spectrum, acting as AGM in Chicago for Roland Hemond (who never played professionally) and in Montreal for Bill Stoneman (who earned Cy Young votes for the franchise of which he went on to be the boss). That’s appropriate, because as baseball epochs have passed and he’s settled into his silver-fox phase, Dombrowski has watched the sport oscillate between two poles of preference for on-field credentials.

Early in Dombrowski’s career, he says, Hemond told him hiring for GMs “goes in cycles.” In the process of steering a record four different teams to the World Series, Dombrowski has observed Hemond’s wisdom be borne out. “I have seen a lot of cycles,” he says, adding, “When I was early in my career as a general manager, a lot of the people that were successful [as] general managers were people who played the game on the field. And then we got away from that a little bit. Now there’s more of those individuals coming back into the game.”

The chart below, based on data provided by Baseball Reference that goes back to 1950, conveys that ebb and flow. The blue line represents the percentage of top executives each year who had been big league players, and the red line represents the percentage who had played in the majors or the affiliated minors (but not, for instance, independent ball, à la A’s GM David Forst). Only the most senior baseball operations executive on each team was included; when teams switched top execs within one year, both were counted, but interim GMs who weren’t subsequently converted to permanent status were omitted.

This year’s rate of ex–major leaguer execs is the highest since 2015, a stat that comes with a caveat: Dipoto, who got his first official GM job in late 2011, was double-counted in 2015 because he spent the first half of the year as Angels GM before resigning and subsequently moving to the Mariners. (Stoneman, Dombrowski’s superior with the Expos, took over on an interim basis in Anaheim.) You have to go back to 2012 to find another year whose rate equals 2024’s, or to 2005 to find a year that surpasses this one’s. Compared to recent rates, this year’s uptick—which could theoretically rise further, if another ex-player is promoted midyear—is a real renaissance, especially considering the deep bench of slightly less senior ex–big league execs whose proximity to a top job isn’t captured by this chart.

Of course, this is still a puny percentage by historical standards: From 2006 through 2023, ex–major leaguer GMs were roughly a third as common as they were from 1950 through 1999, and GMs who had played in the majors or minors were roughly as well-represented as former major leaguers alone used to be. Dipoto, who at 55 is the oldest of the active ex-player execs, made the majors in 1993, when GMs with pro playing experience were the norm and GMs with MLB experience were more than twice as common as they are this year. He describes the difference between then and now the same way Hemond and Dombrowski did: “When I first entered professional baseball, there were quite a few former players that were active general managers. … Then it just went away, and now it’s cycling back.”

There may be more than one reason why the ex-player GM fell out of favor. Ironically, though, the biggest blow to the standing of the ex-player GM may have been dealt indirectly by a team that’s closely associated with one of the longest-tenured ex-player GMs: the Moneyball A’s.

Sandy Alderson, Beane’s mentor and predecessor as A’s GM, was a former Marine but not a former major leaguer. He had innovative, unorthodox ideas, but he lacked the political capital and chutzpah to impose them. “I had credibility problems,” Alderson told Michael Lewis in Moneyball. “I didn’t have a baseball background.”

Beane boasted what Alderson lacked. “Billy had not only played, he might as well wear a sign around his neck that said: I’ve been here, so don’t go trying any of that big league bullshit on me,” Lewis wrote. Beane’s comfort in the clubhouse emboldened him to go anywhere and say anything to anyone; he couldn’t be bullshitted or barred from some inner sanctum where the manager made his decisions free from front-office interference. In Oakland, the manager was more of an instrument of Beane’s will than an independent operator: As Lewis reported, a player who’d recently joined the A’s roster soon realized that “Billy Beane ran the whole show.” Beane had pulled off the power grab that Alderson dreamed of but wouldn’t or couldn’t accomplish: “In what other business,” Alderson had groused, “do you leave the fate of the organization to a middle manager?”

Perhaps more important than Beane’s bloodless clubhouse coup were the team’s results: The A’s won games and made playoff appearances without spending much money, an outcome owners envied. Hiring cycles, Dombrowski says, are usually “reflective of copying, in many ways, who’s winning and successful at that time.” Moneyball as a concept was successful on the field, in bookstores, and ultimately at multiplexes. Other owners wanted Beane clones of their own. But the people who were best prepared to apply and expand the practices the A’s had pioneered or popularized mostly weren’t Beane’s player peers. They were the real-life inspirations for the Moneyball movie’s stathead sidekick, Peter Brand.

Beane himself acknowledges how heavily he leaned on lieutenants who weren’t major leaguers: “The biggest assist to my career was having guys named David Forst, Farhan Zaidi, and Paul DePodesta next to my side. ... If I had to change my playing experience, or having those guys, I’d just as soon never have played.” Playing baseball at a high level in the ’80s, ’90s, and early 2000s hardly prepared major leaguers for future front-office roles in a world where received wisdom and the eye test no longer ruled the roost in team building.

Kapler, whose MLB career ran from 1998 to 2010, says he and his contemporaries were largely out of the loop on the analytical advances that affected their careers: “When I played, I don’t think anybody had any clue how we were being valued, because we were right in that transition period where there were new numbers being looked at.” Flores, a left-handed pitcher who made the majors in 2002 and retired after 2011, sums up the sabermetric sea change: “For a hundred years, baseball organizations thought that some experience in the game, playing in the major leagues, was important in a way for helping decide how to run a major league team. But then with the data revolution and analytics revolution, things were changing so, so fast, at hyper-speed, that the skill sets required and mandated to enact and execute that change were not present in a generation of ballplayers.”

Flores likens the sudden change in the attributes teams valued in front-office talent—and the resulting realignment of the people they employed and promoted—to Netflix’s pivot from DVD distribution to streaming and content creation. MLB’s revolution in player evaluation, and the corresponding new alphabet soup of stats, developed so rapidly that a difference of a few years could determine a player’s exposure to (and, often, acceptance of) the principles that reshaped rosters.

Dipoto, the youthful-looking elder statesman of this squad of active, ex-player execs, is the only one whose whole career predated Moneyball and analytics’ accelerated infiltration of front offices. “I can count the number of front-office analysts that I encountered in the late ’80s and the early ’90s on a finger,” Dipoto says. “There just weren’t very many that you were ever exposed to. Now, that’s an everyday occurrence for everybody in your baseball group, including your players on the field.” Dipoto was introduced to, and intrigued by, the writing of Bill James in the ’80s, but it wasn’t until the first few years after his playing career—especially during a scouting stint in Boston in which he overlapped with James, Theo Epstein, and a few fellow future GMs—that he started to develop his latent interest.

At that point, Dipoto says, he had been in the game for roughly 15 years and was “playing catch-up with people who just entered the baseball world a year or two prior.” He and his contemporaries had to adapt to survive the sport’s seismic sabermetric makeover, but players who came along 10 to 15 years later—like Young, Breslow, Getz, Gomes, and Fuld—“already have that advantage, and now they’re taking those things that they learned through their careers and they’re going to apply them.” Those 40-somethings—plus a 39-year-old, Gomes—played recently enough that MLB’s Statcast cameras tracked them, but even they might trail the true digital natives of today’s game, who’ve been steeped in stats and tech from the start. “The next generation—because I’m sure there will be a next generation—will be even further along in understanding how all of those things make sense,” Dipoto projects.

Players never lacked the desire to put their stamp on teams. What they lacked was the wherewithal, and the demand. “Everyone who plays believes they have all of the answers to solve all of the problems that they faced when they were playing,” Breslow says. That belief leads to “ubiquitous conversations in the bullpen or on the bench about, ‘If I ever had a chance to do this, here’s how different I would do it.’ So I think there’s this inherent management or player-development lens through which all players view the game. I feel like I’ve just been really, really lucky to be in a position where I could actually impact the game in that way.”

In October 2017, FanGraphs’ David Laurila pondered, “Are Today’s Analytically Inclined Players Tomorrow’s GMs?”: a question I returned to in my 2019 book about player development, The MVP Machine. Betteridge’s law loses this round: The first wave of hybrid, player-analyst executives is here. The next wave—composed of the currently active players Dipoto is alluding to—seems equally inevitable, considering ballplayers’ burgeoning appetites for information. Barfield notes, “There’s more and more guys as they’re getting out of the game that are really diving in and becoming experts”—it’s almost a surprise when a player retiree doesn’t immediately move into player development—but there are also more and more guys who are diving in and becoming experts as they’re getting into the game.

The first phase of baseball’s sabermetric overhaul focused on finding players who were already productive but undervalued. The current stage, which Breslow labels an “exponential acceleration of development,” is oriented around player improvement, which depends in large part on players’ participation or initiative. “No longer are players expected to be finished products when they get to the big leagues,” Breslow says. “Information and a better understanding of how information can be applied has shortened the development time frame so that you can walk into a lab and walk out of it with a new slider or a new curveball. … So I think there’s a much greater willingness or openness to trying these things.” Fuld seconds that sentiment. “Maybe 10, 20 years ago there was more resistance from players to take chances and make nontraditional moves,” he says. “And I don’t think that those sort of barriers exist nearly to the extent that they used to.” (They’re finally falling in other sports, too.)

Friedman notes, “A big difference is that now we are getting players into our minor league system that are more versed and aware of data and other ways to value players and various levers that they can pull to get better. … By the time they get to the major league level, they … have a really good feel for things that 15 years ago they weren’t familiar with at all.” Or as Beane puts it, “This generation of players, it’s been a part of their training and upbringing, which I think is very, very helpful in preparing them.” Not just preparing them to play better, but potentially preparing them to be better front-office execs, because, Kapler says, “Some of them are seeking out ways to understand how teams value them, and that probably gives them a leg up.”

Nerds who never played were once a market inefficiency, in Moneyball parlance. Now, the guys who wore jerseys represent a team’s best chance to buy low. It’s Revenge of the Jocks. Except the jocks are nerds now, too.

Photo by Ed Zurga/Getty Images

Let’s stipulate that some former big leaguers, and many of the active ones, have addressed a deficiency that has prevented ex-players from ascending in the front-office ranks for most of this century. Even so, correcting a shortcoming isn’t the same as having an edge. What’s the former major leaguers’ advantage?

Breslow, the latest beneficiary of ex-player execs who have come back into vogue, says that when Fuld and Young got GM jobs, it seemed like “a deliberate correction in the market, in that I think the general narrative had been maybe the sport had become too inclined toward rote analytics and that some of the human elements and culture and experience had been pushed aside. I’m not sure that I agree with that narrative, but I do think that that was the prevailing one. The most straightforward and obvious way to dispute that is to try to find the hybrid profile that could take an analytical and an objective approach to the job while also embodying the experience and empathy that goes along with the playing career.”

Barfield elaborates on this distinction. “For so long,” he says, “it wasn’t players that really had a firm understanding of [analytics], but that stuff can be learned. What can’t be learned is the experiences that you have as a player and what you go through being on the mound, being in the box, the ups and downs, and the things that go on off the field. And I think being able to have an understanding of both sides, it gives you the best of both worlds.” Or, as Kapler puts it, “If you’re hiring a president of baseball ops or a general manager or a similar position, you want the cake and you want the frosting. And I think the executive being a former player is the frosting.”

It’s a compelling pitch. For the past 20 years, owners often faced a choice between a GM candidate who had Played the Game and one who was on the cutting edge. Now, the combo platter is becoming more common. The Rangers can’t complain about their first full season with Young at the helm; will other clubs be happy with these hires? Do fans have cause to celebrate when their team snags a new GM who has his own baseball cards? After all, we’re not selling quarter-zips here.

The job performances of former major leaguer GMs range from Rickey to Hawk Harrelson, so it’s difficult to make any accurate statements about their monolithic merits. If we compare the cumulative post-1950 records of non-players, ex–major leaguers, and ex–minor leaguers, they come in at .503, .496, and .488, respectively—separations of about one win over 162 games—though those are small enough differences to disregard, in light of the limitations of the dataset and the delay in team building between sowing and reaping. In lieu of raw records, we can consider qualitative traits.

“Ideally, if you’re putting together a front office, you’re putting together a front office of people that complement one another, and you complement strengths with weaknesses,” Dombrowski says. One potentially complementary pairing is a non-player with a former player, a yin and yang that non-player Dombrowski pursued by promoting Fuld and Velandia to GM and AGM, respectively, less than two weeks after he was hired. But how, exactly, are ex-players especially well-suited to excel in senior front-office roles, and where might they face a steeper learning curve than non-players who had a head start in an office environment?

To a man, the 10 ex-player AGMs, GMs, and POBOs—as well as Dombrowski and Friedman—testify to the value of a former player’s lived experience. “When you listen to someone’s hardships, you want to be able to say, ‘I know how you feel,’” Breslow says. “When you are sharing your hardships, you want to share them with someone who knows how it feels. So I think the fact that as a former player I have been through winning a World Series and finishing in last place, getting traded, getting designated, getting optioned, getting called up, all of those things, I literally can speak from the position of knowing how those things feel.”

None of which, Breslow allows, produces perfect decision-making. According to Fuld, it could even hurt: “It can be a challenge to divorce your own personal experiences [from] a more global, research-based understanding of what is most important. Just because I experienced something that’s an N-of-1 … doesn’t necessarily mean that that is the most important experience.” However, whether a particular call pays off or backfires, Breslow says, understanding “the implications it might have [for] others, the way that the message is likely to be received, the right time and way to deliver a message, all those things—while maybe insignificant in the moment—compound on themselves, and then I think can have a pretty profound effect on culture and the environment that you create in the clubhouse.”

On the other hand, Breslow points out, “What we’re looking for is not exclusively playing experience. It’s the things that we think come with playing experience.” If teams are looking for front-office leaders who are, as he recites, “relatable and personable and empathetic and smart and diligent and organized and disciplined,” then well-educated athletes who made it to the majors seem likely to fit the bill. But plenty of candidates who can’t hit a breaking ball (or throw one) check a bunch of those boxes too.

Plus, while dashing someone’s dreams isn’t fun for any boss, it can be extra painful for a former player to conduct the kinds of difficult conversations that they once experienced from the other side. “Everybody remembers when they’re released,” Barfield says. “You remember exactly what you’re wearing, what you’re thinking, the room you were in.” Knowing how to handle dispensing bad news may make it easier to cushion the blow, but the burden of being the bearer of bad news makes for guilt-inducing role reversals. “The fact that you may see yourself in the person you’re talking to makes it even a little more uncomfortable,” Dipoto says. Fuld echoes that sentiment, saying, “It was and continues to be an adjustment for me, and I’m sure for other former players that have to deliver difficult news. You’re not often, if ever, a ‘bad guy’ as a teammate.” Young says that being the bad guy—albeit in the nicest way possible—“was one of the things I really was worried about when I took the job, is that those conversations with players, the hard conversations, and having been on the other end of them, I didn’t know how I would be able to handle those.”

Some conversations are hard not because they’re about cutting a player loose, but because they concern convincing a player to try something new and daunting. In theory, having been a big leaguer makes that an easier sell. “It’s just a little bit of instant credibility,” Kapler says. “‘I did this thing that we’re asking you to do, I made this adjustment that we’re asking you to make, I looked at these things that we’re asking you to look at, and here’s how it served me’ is a really nice sales pitch.” With more tools to help players improve, more prospects who are being promoted quickly, and more emphasis on development at the major league level, the power of persuasion is increasingly valuable.

Then again, that intrinsic power may have dissipated. Today’s players are accustomed to analyzing themselves and accepting feedback from coaches and analysts with nontraditional résumés, so it’s not a given that they’ll be wowed by the words of an ex-player GM (even if, unlike Herrmann with Dipoto, they realize they’re talking to one). And after the relative lull for former players in front-office positions of authority, the ex-player aura may have lost a little luster upstairs too, as Dipoto points out: “Maybe in the early 2000s, you go into a front office or an organizational meeting and you sit down with 50 baseball personnel—not players, but scouts, player development people. Being a former player gave you a sense of belonging, or you had hit some level of respect when you walked in the door. … I’m not sure that you have instant credibility anymore. You have to earn that. You’re starting fresh in a new job; you just happen to have a baseball card, and other guys don’t.” Per Barfield, “Players don’t care nowadays what you did. They care about how much you can help them.”

However, being a former big leaguer still helps forge connections to other former big leaguers. And because Beane, among others, helped dismantle the idea that front offices and field staffs operate semi-autonomously in separate spheres—“A manager is now an extension of the front office,” Breslow notes, which helps explains why former players like Kapler, Fuld, and A.J. Hinch have been courted in both capacities—GMs are in near-constant communication with managers and their ever-growing coaching staffs, where former players still predominate. “The benefits of collaboration with coaching staff and interfacing with players [have] grown increasingly important,” Fuld says; consequently, Breslow adds, so has “the ability to cut into that divide that otherwise could be a real hurdle.” Not that ex-player GMs and ex-player managers always get along, as Dipoto could confirm.

Professional baseball is a small world, and in some cases, GMs and managers or coaches have preexisting connections that get flipped as former players climb to the top of a front office. Beane had played in winter ball for Art Howe, who was managing in Oakland when Beane succeeded Alderson. “One year I’m playing in winter ball, next year I’m, technically, I guess, his boss,” Beane says. Bruce Bochy managed Young in San Diego; Young hired him in Texas. “I think I treat it like Boch is my boss,” Young jokes. Breslow and Red Sox manager Alex Cora were briefly teammates on the 2006 Sox; now they’re teammates in very different roles on the 2024 club. “We’re still building our relationship, but many of our conversations are just the way that two teammates would talk to each other,” Breslow says. “There’s an authenticity to that that’s just really difficult to replicate.”

Chumminess can lead to awkwardness when business and friendship intersect. When Breslow hired one of his best friends, Andrew Bailey, to be Boston’s pitching coach, they “had to talk through negotiating a salary and all of those things.” Honesty has been Breslow’s best policy: “I think we established early on, ‘Hey, if this is going to work, we need to be willing to have difficult conversations.’”

Working with a pitching coach is, at least, a lot less inherently adversarial than, say, salary arbitration. In 1990, Beane and Mike Bordick were friends and teammates with the A’s in spring training; four years later, AGM Beane was negotiating Bordick’s contract in arbitration. “I think he found it more humorous,” Beane says. “I found it a little bit stressful.”

Flores knows the feeling. On the front-office side, he says, “Players aren’t comfortable always thinking of surplus value or trade value or diminishing age curves or arbitration value versus free agent value versus replacement level. Those are just sometimes terms that you’re uncomfortable with as a player, but you have to be fluent in them because that’s the operations side that you work with.” No one knows what a bummer arbitration can be better than a player who’s been through it. “Doing it from the other side,” Flores continues, “my only hope is that my counterpart understands that I do have empathy, and I do have understanding for that side, but that there’s a job to do on this side.”

Getz, who joined the Royals front office shortly after his final season, says, “You have to be very mindful of how and what is being communicated to the players that you maybe have a history of being close to. So I was made aware of that early on and mentored in [how to] put your guard up.” On a more positive interpersonal front, former players come preprepared for fielding calls from agents. “If an agent is talking to you about a potential free agent or their own players within your organization, it’s a very fluid, easy conversation because you’ve probably had it 500 times before just through your playing days,” Getz says.

Moreover, shared membership in the brotherhood of baseball players often aids inter-team communications, just as it helps bridge the intra-team gulf between front office and field staff. Almost unanimously, ex-player execs agree that though they’ve forged strong bonds with rival execs who weren’t players—including some who previously employed them—the past experience of playing with or against a front-office counterpart is an automatic icebreaker.

“Sometimes it can be intimidating to call other clubs or other executives, especially when you’re new at the role,” Young admits. “They have different experiences, they’ve had different levels of success, and, to some degree, you’re trying to figure out what you’re doing and learning your way. And so when you have those former colleagues that you’ve played against, I think it does facilitate maybe easier relationships.” (It’s nice to know that even people who’ve pitched three scoreless extra innings to win a World Series game can feel anxious about a phone call.) Sometimes, these loose connections are codified into formalized matches. “As we go through the exercise of trying to assign contacts with the organizations, it’s just like, ‘Oh, obviously I’ve got that one; we played together,’” Breslow says.

Young and Fuld’s on-field face-offs were fruitful for Fuld, who went 5-for-10 with two homers and a double against the tall righty, yielding the highest OPS he posted versus any pitcher he faced at least 10 times. (“Yeah, he was the one,” the glove-first Fuld jokes when reminded that he hit well against Young. “That’s it. It’s a short list.”) That history made their post-playing conversations more seamless, and years later, they linked up again on the first trade Fuld ever executed, a 2021 swap centered on Kyle Gibson, Ian Kennedy, and Spencer Howard. (Another hit for Fuld.) But even ex–major leaguers whose careers didn’t overlap can easily bond over having been in the bigs. When Dipoto talks to younger ex-player execs, he says, “I do feel some kind of connection because there’s only a certain number of people alive that got to do what we got to do.”

While they were doing that, though, there were some things that they didn’t get to do. “There’s a ton that, as a former player, I didn’t have exposure to that I’ve had to learn in the chair,” says Young, who benefited from a stint in the league office before he joined the Rangers. “Somebody who comes up through a front office may have more exposure to those things and not as much to locker room experiences that I had.” Or as Breslow puts it, “While I was playing, others were in a front office and gaining experience in negotiating or familiarity with the CBA.”

In earlier eras, when players were more often elevated to lofty front-office roles, Young notes, “the operation was smaller.” Now, ex-player GMs are tasked with managing hundreds of people—an unfamiliar challenge for individuals who spent their playing careers focusing almost exclusively, and obsessively, on their own performance. They’re also asked to serve as a spokesperson for an entire organization, not just themselves, and to oversee—and help budget for—departments they might have known little to nothing about when they were in uniform, such as international scouting, research and development, medical, and sports science. “I don’t necessarily think my having played made me a better decision-maker in terms of running the business,” Beane says.

Even the aspects of running a team that they were familiar with turned out to be more complex than they would have suspected. “When I first came in on the development side, I had no appreciation for how much time and effort and thought goes into delivering each and every message to players,” Gomes says. “It is countless hours that go into a potentially five-to-10-minute conversation in making sure that everybody’s aligned and messaging the right thing.”

Thus, Young concludes, “Just because players understand aspects of the information or the analytics, there’s so much more that comes with running an organization and building a successful team. … It helps if you speak some of the language, but it doesn’t mean you have all the other aspects figured out.” Small wonder, then, that many of the ex-players refer to their first, faltering front-office steps as back-to-school-style immersion courses conducted by veteran mentors. “When players or ex-players came in or worked with us, I wanted them to immediately forget everything and the opinions they gathered as a player,” Beane says, adding, “and then ultimately over time, I think you bring your playing career back into it and your experiences, but I wanted guys to start from scratch.”

When Dombrowski was starting out, Hemond advised him, “You’re not going to learn about the game by staying in the office.” The older executive encouraged his protégé to travel with teams to fill in the blanks in his schooling in the sport. Now Dombrowski does the opposite for his player protégés who lack book learning, telling them, “Here’s a basic agreement. Go ahead and read it. Here are the rules.”

Based on his experience with ex-player execs, Friedman explains, “The cadence of a season, an offseason, is something that they can’t possibly have a feel for in advance of living it. Just how fluid the calendar is and just the different transactional points of the season and what all goes into that is eye-opening.” Once their eyes are open, they can pick their path. One of baseball’s breakthroughs in player development, Friedman says, has been “individualizing player plans” rather than forcing every athlete to conform to the core philosophies of a farm system. The same approach applies to the development of budding baseball execs. “We try to set up the onboarding on the front end to align with things that they know they’re interested in and then give them exposure to other things and get a feel from there what they’re most stimulated by and try to point more of their bandwidth in that direction.”

“I think the lack of experience is obvious,” Friedman says. “But I think on the flip side, the fresh perspective has a lot of value as well.”

So that’s the reward for ballplayers who beat the odds by working their way up to the pinnacle of their profession and then decide to start a second career. They go back to being rookies and try to do it all over again.

“Players today know there’s a path to these spots now that they’re seeing examples of it,” Flores says. How many more might want to walk it?

To answer that question, it might help to examine what the current class has in common. Speaking of the discomfort with replacement level that Flores cited: Young is the only one of these 10 ex-player execs whose career WAR cracked double digits. Although many of them lasted a fairly long time in the majors, their places were rarely secure. “I was always that last man on the roster,” Flores says.

Maybe that’s not so surprising. Most major leaguers aren’t stars, and as Beane says, “Being world-class in multiple things is pretty rare.” And then there’s the not-so-small matter of money: A player who earned tens of millions or more may be less inclined to commit to another hectic, high-pressure occupation. “There is no Fourth of July family at the lake when you’re a player,” Flores says. “There is no, ‘I’m going to take a day and go to the wedding.’ There is no, ‘Hey, after school, happy hour with the parents from my kid’s second-grade class.’ That doesn’t exist for however long you play.” After those playing days are done, he adds, “A lot of players want a life that is absent the all-in nature required of these roles.”

But might their marginal talents (by big league standards) have helped set up their successful second acts? As they clung to careers on the fringes, Getz says, they “needed to exhaust all kind of areas to improve their game to survive. I think that there’s a level of—I don’t know if grit’s the right word, but a constant pursuit of improvement.”

As a front-office executive, Gomes is “a star,” Friedman says. As a pitcher, he sometimes struggled to stay on Friedman’s Rays rosters. Those struggles made him smarter and more familiar with front-office machinations. When he’d get demoted to Triple-A, he would ask why, and the answer—the rotation needed rest, perhaps, and he had minor league options remaining—taught him more about the business of baseball. “It just was a way to rationalize, like, ‘Oh, OK, I understand this,’” he says. And because his presence on the roster hung on a knife edge, he was always hungry to hear how he could avoid getting cut. “I was curious about: When I was successful, why was I successful? When I wasn’t, why was I not successful? And they were always open to sharing behind the curtain of why that was. Like, ‘Hey, you should lean on your slider more here.’ Or, ‘Hey, you should think about throwing this pitch less.’”

Maybe it’s a matter of the right minds meeting on the right team at the right time. Velandia played for the A’s in the late ’90s and in 2000, when players had to walk at least 10 percent of the time to qualify for the franchise’s Player of the Month award in the minors (and earn some swag). “It got my mind into thinking, honestly, this is interesting,” he says. It’s not a coincidence, Fuld says, that a seemingly disproportionate number of analytically oriented ex-players once suited up for the forward-thinking Rays. (He, Gomes, and Diamondbacks special assistant to the GM Burke Badenhop were teammates in Tampa, and Kapler played there too.) “When I was there, we were shifting before most or any clubs were doing that; we were platooning in a way that was different than most or all clubs. … You can’t help but appreciate and connect those dots that some nontraditional, evidence-based decision-making [can] … help teams.”

But why did the spark catch in these particular players and not other A’s, Rays, or Dodgers? Friedman says, “The style in Tampa Bay, the style in Los Angeles, is to be open and sharing of information. And so for people who are curious, it definitely enhances that part of their brain with the access.” In other words, the curiosity comes first. Breslow didn’t become a chief baseball officer because his late-career experiment in remaking himself as a pitcher eased his transition to a front office. He became a chief baseball officer because he had the impulse to experiment in the first place. “You always wanted to find the answer,” Velandia says. “And that was, I think, the thing that we all have in common.”

Friedman says that while a previous relationship with an especially open-minded player “definitely sticks with you,” he doesn’t actively scout inquisitive players as future front-office material. “I prefer it to be more driven from them once their career is over and then take the conversation from there. [I] don’t want to ever be in a position where I’m trying to talk someone into doing this, because it’s obviously a huge commitment.” But Breslow says teams do monitor and recruit potential execs-in-waiting. “Whether we’re willing to admit that or not, it does happen.”

Whether the link between pedestrian playing performance and superior performance in front offices is correlative or causative, those on-field failures pay dividends down the road. “I wasn’t nearly as good as essentially everybody on our major league team,” Gomes says, referring to the current Dodgers roster. “So there’s a humbling factor, and I think you never forget how hard the game is.” Nor do you ever stop imparting that takeaway to others. “My experience as a player really helped me, in general, with my own staff as we made decisions, to remind them how difficult the game is,” Beane says. “And all I had to do was pull up my stats to remind them how difficult it was. ‘You guys, look how bad I was. It’s really hard.’” (It’s incredibly hard.)

One thing seems certain: Ex-player execs beget more ex-player execs. Stewart hired Barfield; former Phillie (and Phillies GM) Rubén Amaro Jr. hired Velandia. In addition to bringing in Barfield, who had been the Diamondbacks’ farm director, Getz has anointed Brian Bannister as senior adviser to pitching and Paul Janish as director of player development (Getz’s old job). And the Dodgers, having seemingly struck front-office gold with Gomes, have recently loaded up on ex-player advisers and assistants such as Tyson Ross, Nelson Cruz, and Chris Archer. “I think it’s a good thing for baseball when people that have been involved in the game for really our entire lives, at least our work lives, stick around,” Dipoto says.

In an earlier era, the pipeline of ex-players funneled to front offices and coaching staffs smacked of boys’ club cliquishness. Perhaps it still does. “When you start hiring people just because they played or not, or that being the first thing on your checklist, then really bright executives like Kim Ng don’t get the opportunity,” Beane says.

However, we’re so far removed from the days when teams shunned non-players that the power imbalance between those who did and didn’t play has been inverted. As I wrote in 2019, “Although it’s a sign of progress that nonplayers are no longer excluded from the team-running ranks, front offices have swung so far in the other direction that they’ve merely traded one type of homogeneity for another.” Entrusting top jobs to players has become, in effect, a means of promoting diversity—but only one kind of diversity.

Many of the players who’ve gotten these gigs are demographically indistinguishable from the non-players who’ve tended to: white, male, and Ivy League educated. Breslow went to Yale, Young went to Princeton, and Fuld went to Stanford. “Ultimately, we want to live in this world where the results speak for themselves and diversity of backgrounds and ethnicity and thought are not just respected, but highly sought after,” Breslow says. “I think we’re getting there, but it takes a deliberate and intentional approach to building that out because otherwise, you end up with a lot of people who all look the same, figuratively. The irony here is: As a player, I was unique because I went to Yale, and as a GM, I’m unique because I played baseball.”

Dipoto believes that “the next group will look a little bit more diverse … in race or gender, it will look a little bit more diverse in background, because that’s the way we evolve as a society, as a game. … Slowly but surely, we’re evolving in a positive direction. I would love it to happen quicker, but I do believe that the return of the former player as a general manager [is a] very positive thing in the game.”

Maybe the most positive sign is that Velandia—MLB’s first Venezuela-born AGM—Gomes, Flores, and Barfield don’t fit the largely lily-white, elite-educated mold. “You’d love to see that continue to grow, specifically with minorities,” Barfield says. “I think that it has gotten better the last four or five years from where it was, probably. A little slower than most of us would hope.” Barfield wants to be a GM, and not just because he’d enjoy the job. “I think it’d be really cool to be able to tell people, ‘I graduated from University of Phoenix and was able to get this. You don’t have to have the fancy degree. You just really have to just want to learn and grow and have that hunger for knowledge.’” And although you don’t have to have played ball, it might help, for the first time in a while.

Thanks to Kenny Jackelen of Baseball Reference for research assistance.