Welcome to the holiday season, one that is even better if you live in a part of the world where you don’t need to worry about snow, ice or broken heaters. Then again, if you live in a region (Florida) where people should not be driving (Florida) or where they seemingly forget how to shop (Florida), maybe it evens out. But at least we have the MLB offseason to keep us entertained!
Things have certainly been busy in the baseball world, and plenty of free agents have gotten their gifts early in the form of new contracts and new homes. Some of the executives who signed — or didn’t sign — those contracts have made their way to the naughty list, though.
For this list, we’ve listed all executives alphabetically — and, yes, we said “executives.” Some organizations still call their lead decision-maker the “general manager,” while others opt for “president of baseball operations” or something similar. For teams where a general manager reports directly to someone who is not the owner, as is the case in Cincinnati with Brad Meador (general manager) and Nick Krall (president of baseball operations), we’ve opted to include both men.
Honorable mention: Ben Cherington, Pittsburgh Pirates
Consider this our holiday gift to Cherington, who has been the Pirates’ lead baseball executive for six seasons, all of which have ended with losing records. The only reason why Cherington is an honorable mention rather than a full-fledged member is that the Pirates reportedly offered Phillies slugger Kyle Schwarber a four-year contract worth roughly $125 million during the Winter Meetings. Although Schwarber opted to remain with the Phillies on a five-year, $150 million deal, at least the Pirates made what seems to be a genuine effort.
As we argued elsewhere, the Pirates need to build off that momentum and pursue veteran free agents worthy of multi-year deals. The days of bargain bin hunting for players that they can flip at the trade deadline should be over. If Cherington wants to field a winning team with Paul Skenes as his ace, he must seriously try to make meaningful additions. Let’s see if he follows through, if only to avoid landing on next year’s version of this list.
Alex Anthopoulos, Atlanta Braves
Of all the executives who actually made this list, Anthopoulos is probably the one with the least amount of coal in his stocking. The consensus is that last year’s 76-86 finish, the Braves’ first losing record since 2017, was likely an aberration. We won’t fault Anthopoulos for the injuries to Chris Sale, Ronald Acuña Jr., Spencer Schwellenbach and others.
So, what’s the problem? Well, we feel like the Braves are being too aggressive, which only increases the risk of things falling apart. Signing Robert Suarez to a three-year, $45 million contract as a setup man carries significant risks. Last year’s Jurickson Profar contract (three years, $42 million) was already concerning because he was coming off a career year at age 31, and then he served an 80-game suspension following a positive test for performance-enhancing drugs. It’s hard to blame any Braves fans for wondering how “legitimate,” for lack of a better word, his .839 OPS and 3.6 bWAR were for the Padres in 2024.
As we’ve said before, all is forgiven with a championship. Still, the Braves’ last two offseasons reek of desperation, and that’s rarely a winning formula in any sport.
Brad Meador and Nick Krall, Cincinnati Reds
Much like Cherington and the Pirates, we saw Meador, Krall and the Reds frequently linked to Schwarber throughout free agency. However, there’s a key difference. Schwarber had no ties to the Pirates, and they seemingly offered him a contract, believing that he’d upgrade their lineup and help Pittsburgh return to the playoffs for the first time in over a decade. Makes sense, right?
Well, then there are the Reds. ESPN’s David Schoenfield reported on Dec. 17 that the Reds likely only pursued Schwarber, an Ohio native who grew up a Reds fan, to boost ticket sales … which means that they probably won’t go after Cody Bellinger, who is originally from Arizona, despite still having space in the outfield to upgrade. Let’s reiterate that Cincy just reached the postseason for the first time since 2020. Winning teams and a buy-in from ownership help ticket sales far more than a hometown hero. Congratulations, gentlemen, you easily earned a spot on our list!
Brian Cashman and Hal Steinbrenner, New York Yankees
When you’re a sports figure in New York, you’re almost always destined to wind up on lists like these. Our specific issues with Cashman, at least right now, are how he’s handling the Jazz Chisholm Jr. situation. Even the Yankees fans who aren’t the biggest fans of Chisholm’s loud, unfiltered personality would agree that he’s a special player, one who is fresh off becoming only the third player in franchise history with a 30-30 season. Yet, Cashman has played the passive-aggressive game all offseason, not ruling out trading the two-time All-Star before he hits free agency next winter.
With respect to the Rockies or Marlins, the Yankees are not the Rockies or Marlins. They haven’t won the World Series since 2009, and they’ve captured only one pennant during that time. Perhaps the greatest misinterpretation that Cashman and owner Hal Steinbrenner have is that it’s not about acquiring marquee talent; it’s about retaining said talent. Chisholm is a fan favorite, he has a swing made for Yankee Stadium and we have immense faith that he’ll be a key piece of the 2026 Yankees.
As for Steinbrenner, he owns the Yankees. Why is he talking about the Yankees’ budget and how the team allegedly lost money? This franchise has one of the most recognizable and profitable brands of any North American sports team. But he wants to lower payroll? Those two are why the “facepalm” emoji exists on your smartphone.
Chaim Bloom, St. Louis Cardinals
What do the Cardinals want to do? Are they a rebuilding team or a transitioning organization that still believes that they can compete for a playoff spot in 2026? Trading veteran starting pitcher Sonny Gray to the Boston Red Sox makes us think St. Louis is leaning towards the former, yet third baseman Nolan Arenado is still on the roster. The argument that teams might not want to trade for Arenado, a 34-year-old with two years and $31 million left on his contract, only goes so far in an era where clubs eat money when needed.
The Cardinals have losing records in two of the last three years, the first time they’ve accomplished that feat in nearly 30 years. Much of that falls on Bloom, seeing as he’s the team's new lead baseball executive, and it’s time for him to get things back on course.
David Stearns and Steve Cohen, New York Mets
For their sake, let’s hope that Mets fans don’t actually try to mess with Stearns’ or Cohen’s stockings this holiday season. The same fan base that endured the Wilpons and all of the drama during their tenure has already turned on Cohen and Stearns following an epic second-half collapse and the departures of Edwin Díaz and Pete Alonso in free agency. Oh, and we can’t forget the controversial decision to trade longtime outfielder Brandon Nimmo to the Texas Rangers for second baseman Marcus Semien.
If the Mets somehow win the 2026 World Series, then we imagine that only a select few fans will forever hold the Alonso, Díaz and Nimmo decisions against Stearns and Cohen. With that said, does anyone truly believe that the Mets can take down the Phillies, Dodgers, Brewers, Cubs or even the Braves in the National League? If you turn on a Mets game next spring and Citi Field is emptier than you’d expect, it shouldn’t be hard to figure out why.
Scott Harris, Detroit Tigers
Does Scott Harris realize that he has a two-time AL Cy Young winner in Tarik Skubal? He does? Good. We’ve said this before, and we’ll repeat it: Either trade Skubal now, or make it clear that you intend to keep him in Detroit until further notice. Harris is the latest executive to tiptoe around the idea of trading an elite player, telling reporters that no player is “untouchable” in trade talks.
The problem, at least as we see it, is that Skubal isn’t an above-average player. He’s arguably the best starting pitcher in baseball right now, and if he’s not No. 1, then he’s 1B alongside Paul Skenes. We understand that the Tigers are likely unsure whether Skubal will sign a long-term extension within the next 12 months. At the same time, Detroit has reached the ALDS in consecutive seasons, and they play in the eminently winnable American League Central. There is still a window of contention that the Tigers should capitalize on … or they should get started on the rebuild now and trade Skubal.
Of all the lead executives on this list, Harris is probably the one we’re most irritated with, if only because he and the Tigers seemingly won’t commit to one direction. Again, this isn’t an instance with a 100-loss team weighing trading an All-Star. This organization has made consecutive postseason appearances and has the two-time defending Cy Young winner on its roster. Do we need to go any further?