Looking Toward the Future, the Rockies Are Begging for the Past

Most major league baseball organizations think more or less the same way. They vary on tactics and strategy, in competency, in resources, and in culture, but for the most part everyone agrees on how to win a baseball game. This leads to some groupthink and a lot of same-y executive hires.

The Giants have bucked the trend, turning back the clock to hand the reins to an ex-player who’s long on cultural cachet and short on expertise. He, in turn, made a delightfully unorthodox choice for field manager. I look forward to seeing if these iconoclasts can hold their own.

Not to be outdone, the Colorado Rockies have gone even further off the board for their new head of baseball operations, as they are reportedly nearing a deal to hire Paul DePodesta for the position. I’ll be as blunt as I can be: It’s one of the weirdest executive hires in decades, from an organization that’s at least a full step behind its rivals to start. With all the best will in the world, unless DePodesta’s appointment heralds a complete change in organizational structure and philosophy, it is almost certainly doomed to fail.

The Rockies went 43-119 this year, and it’s not because they’re cursed, or because their home city has checked out, or because their owners don’t care. They ran a higher payroll this season than three playoff teams. They lock up their homegrown success stories, such as they are, to contract extensions rather than shipping them off the moment arbitration hits. Their record free agent signing, Kris Bryant, is on a richer deal than anything the Astros, Blue Jays, Braves, or Cardinals have ever given out on the open market.

The Rockies’ problems, unfortunately, are worse than apathy. I wrote about them in May, right after they’d fired manager Bud Black, while they were on a 28-win pace. Read it if you’d like; I’ll just quote the paragraph that diagnosed their problems:

The Rockies, it turns out, are famously insular. They like and trust Their Guys, and are loath to turn over personnel or chase the latest innovations. In almost any other industry, that quality would be benign at worst, or even laudable. But baseball is zero-sum. If you’re not advancing, you’re falling behind. And since Black last led the Rockies to the playoffs, the industry-wide rate of innovation has only exploded.

I’ll say this for Rockies owner Dick Monfort: He is finally bringing in outside help. This was not a given. DePodesta is only the fifth baseball ops chief in franchise history, and the first external hire since Dan O’Dowd in 1999. Looking outside the family is a good start, but DePodesta was far from the first choice.

The list of candidates was impressive. It included former Twins GM Thad Levine, former Astros GM James Click, Royals assistant GM Scott Sharp, Guardians assistant GM Matt Forman, and Diamondbacks assistant GM Amiel Sawdaye.

Levine, Forman, and Sharp have built, or helped to build, winning teams on middling budgets. Click won a World Series with one of the most dominant teams of the past decade, even as his boss was standing over his shoulder the whole time like the Grim Reaper. Sawdaye won three rings with the Red Sox while working his way up the ladder in the scouting department; from there, he followed Mike Hazen to Arizona, where they won the NL pennant in 2023.

If I were in the market for a guy to build a respectable ballclub from scratch, without spending $300 million a year on player salaries, I’d feel OK about hiring any of those guys.

None of them wound up with this poisoned chalice.

What of DePodesta, then? He’s more famous in baseball circles than most MLB GMs, due to his stand-in character’s presence at Billy Beane’s elbow throughout the events depicted in Moneyball. At 31, he was given the keys to the Dodgers, whom he ran for two tumultuous seasons before being fired by then-owner Frank McCourt. (Which is not inherently a strike against him, McCourt’s reputation and baseball acumen being what they were.)

DePodesta spent the next decade working in the Padres and Mets organizations, and as the VP of player development and scouting for the latter, helped build the monster pitching staff that took New York to the 2015 pennant.

I have no doubt that DePodesta could’ve gotten another chance to run a major league team before now, but in January 2016, he made the shocking move to the Cleveland Browns of the NFL, where he spent 10 seasons as chief strategy officer.

The Browns were then as the Rockies are now; seen as irrelevant, innumerate, insular, and backward. DePodesta was given a long leash to remake the club as he saw fit. He beefed up the analytics department, stockpiled draft picks, and sought to target undervalued players, just as he had in baseball.

Before the 2019 season, my employers at the time, The Ringer, ran a themed package called “Trust the Browns’ Process Week,” based on the premise that DePodesta’s team was about to turn a corner. This editorial decision was made far above my pay grade; I don’t know a lot about the NFL, but I know better than to get over one’s skis about the Browns.

As part of this project, it was decided that I would interview DePodesta for a feature. My premise was that baseball was so far ahead of the other major sports in terms of empirics and analytical integration, a smart football (or basketball or hockey or soccer) team could get a five-year jump on its rivals by hiring the right baseball nerd with interdisciplinary skills.

“More than anything, we try to make information as accessible and actionable as possible,” DePodesta told me then. “There’s a lot of interesting stuff. There’s a lot of neat stuff, but if it’s not actionable, it just isn’t relevant, and what we’re really trying to do is support both our coaches and our personnel people in their decision-making process.”

In hindsight, what DePodesta said about team-building was reasonable enough, and while he was cagey about what specific insights he brought to the NFL, I was able to tease out that the new market inefficiency was wide receivers who’d had crappy college quarterbacks. But the Browns went 6-10 in 2019.

That is not to say DePodesta’s tenure in Cleveland was a total failure. He made the playoffs twice in 10 years, which is a lot when you consider the franchise had only made the playoffs once in 17 seasons since it was reincarnated in 1999. DePodesta’s Browns brought the franchise its first 11-win season and first win in a playoff game since 1994. (And you thought the Rockies had it bad.)

Even with those highs, DePodesta didn’t cover himself in glory in the 2020s. I said earlier that I don’t know that much about the NFL; my former colleague Rodger Sherman knows vast amounts about the NFL, and when news of DePodesta’s hiring broke, he offered the following:

still remarkable that the Deshaun Watson trade/signing backfired so completely that it's probably the worst NFL transaction of all time …
…
…
BEFORE you mention the dozens of allegations of sexual assault that the Browns knew about and ignored

— Rodger Sherman (@rodger.bsky.social) November 6, 2025 at 4:57 PM

It would’ve been troubling if DePodesta had profited from buying low on a talented player who had been revealed to be a(n alleged) serial sexual predator. But it wouldn’t have set him apart from any number of baseball executives. But DePodesta dug himself deeper into a hole when he described the team doing its due diligence on Watson around the time of the trade.

“This has been the most detailed and dogged potential acquisition of a player that I’ve ever witnessed,” DePodesta said. “I mean, now in 25-plus years across two different sports, I’ve never been a part of anything like it. As we got more and more information through all the steps that we took, all the diligence that we that we undertook, all the people we talked to and all the additional information we got and especially the perspectives we got from some of the different people involved or much more involved with him, ultimately got to the same place … where we were really comfortable with the person.”

Pro sports teams make this moral compromise more than most of us would like, because when the opportunity arises to acquire a great player on the cheap, the temptation can be great.

Except, that’s not what DePodesta did. He shipped out six draft picks, three of which were first-rounders, including one the Texans used to select future Rookie of the Year Will Anderson Jr. Watson then got a record-setting five-year, $230 million contract extension, and repaid the Browns by playing 19 games over four seasons and posting the 42nd-best passer rating out of 50 quarterbacks with at least 15 starts since 2022. This year, the Browns spent not one but two draft picks on quarterbacks, and Watson hasn’t played a snap.

I’d question the judgment of anyone who sold his soul to the devil. All the more so when he didn’t even get anything back.

Meanwhile, the franchise QB DePodesta and I talked about, Baker Mayfield, is doing just peachy with the Buccaneers. And the Browns finished 30th out of 32 teams in the most recent NFLPA survey on working conditions.

When DePodesta made the jump from baseball to football, there was plenty of reason to believe in him as an evaluator and decision-maker. He’s done quite a bit of damage to that reputation in the intervening decade.

Especially because baseball has changed so much since he’s been gone. I presume that DePodesta’s been in touch with his old buddies from his previous career, that he knows about fastball shape and swing speed in general terms. But this is a scouting and development guy whose last year working in baseball was the first year of Statcast. The learning curve is going to be so steep it might as well be vertical.

And if the Rockies were in position to ease that transition in any meaningful way, well, to be honest, they would’ve been able to hire someone like Sawdaye.

So what we have here is a team that lost 119 games this past season, with worst-in-the-league scouting, analytics, and development programs, a meddling owner, and the unique challenge of playing in a city where curveballs don’t break. And the man the organization has brought in to make up the gap to its competitors is himself 10 years behind the times, with some serious questions about his judgment emanating from his time in the NFL.

I don’t like making predictions in absolute terms; baseball is so capricious you’ll look like a fool if you use words like “never.” It’s possible that DePodesta could be the man who revolutionizes the Rockies, gives them their first extended run of competitiveness. It’s possible, but it’d take a miracle.