This is no secret: Front offices are smarter than ever and, believe it or not, make fewer mistakes than ever. Fewer big mistakes, at least. Consider some of the players traded as prospects last decade (from 2010-19): Yordan Alvarez, Zack Wheeler, Max Fried, Trea Turner, Luis Castillo, Sandy Alcantara, Zac Gallen, Dansby Swanson, Fernando Tatis Jr., Dylan Cease, Anthony Rizzo, Patrick Corbin, Lucas Giolito, Willy Adames, Jesus Luzardo, Gleyber Torres.
That's six of the top 12 pitchers this decade via WAR and five of the top 30 position players. Some of the deals worked out for the teams trading away the prospect: The Cubs won a World Series with Aroldis Chapman (traded for Torres) and the Nationals won a World Series with Adam Eaton (traded for Giolito) -- but most did not.
We're halfway through the 2020s and we haven't seen nearly as many of those kinds of trades (so far, anyway). Top prospects are the gold currency of MLB, to be parted with only in acts of desperation. But mistakes have still been made: bad trades, bad signings, bad decisions in the playoffs. Stealing an idea from ESPN NFL writer Bill Barnwell, we're going to dig up the worst decision each team has made through these past five years, evaluating the outcome and not the process.
We'll start with the least damaging of the moves and end with the biggest mistake so far of the 2020s.
Jump to a team:
American League
ATH | BAL | BOS | CHW | CLE
DET | HOU | KC | LAA | MIN
NYY | | SEA | TB | TEX | TOR
National League
ARI | ATL | CHC | CIN | COL
LAD | MIA | MIL | NYM | PHI
PIT | SD | SF | STL | WSH
30. Baltimore Orioles
Biggest mistake: Trading Tanner Scott to the Marlins (April 2022)
The Orioles began the decade as the worst team in baseball: From 2018 to 2021, no team lost more games -- and no other team was even close. Miraculously, the Orioles suddenly turned things around as a long dormant farm system began churning out talent. The Orioles went from 52 wins in 2021 to 83 in 2022 and then made the playoffs the past two seasons, including a 101-win division title in 2023. To do that, you aren't making many mistakes along the way, and the Orioles have drafted well, traded well and picked up some free talent along the way.
One mistake, however, was giving up on Scott too soon. He had been with the Orioles for parts of five seasons but remained wild and posted a 5.17 ERA in 2021. The Orioles sent Scott and Cole Sulser off to Miami for three low-level minor leaguers, none of whom have played past High-A. Scott, meanwhile, finally put everything together and emerged as one of the best relievers in the game the past two seasons with a 2.04 ERA and 188 strikeouts in 150 innings. The Orioles could have used him in the 2023 postseason and having Scott would have prevented the need to sign Craig Kimbrel as the closer in 2024 to fill in for the injured Felix Bautista.
29. Pittsburgh Pirates
Biggest mistake: Drafting Henry Davis first overall (July 2021)
It seems weird to say about a team that hasn't had a winning season this decade, but the Pirates haven't made any huge gaffes -- it's been more like losing by a thousand little cuts. Of course, when you get the first pick in the draft, you want to hit a home run, like Pittsburgh did with Paul Skenes in 2023, but that hasn't been the case with Davis.
To be fair, there was no consensus top player that year and the rest of the top 10 doesn't look like it's going to be a star-studded group, so we'll cut the Pirates a little slack. Still, they struck a deal with Davis to sign below slot -- four of the next five picks all signed for a larger signing bonus -- and the Louisville catcher just hasn't hit as projected. He has played 99 games in the majors, produced negative WAR and hit .144 in 37 games in 2024. You would certainly take Jackson Jobe, Marcelo Mayer or Jordan Lawlar at this point over Davis.
28. San Francisco Giants
Biggest mistake: Signing Mitch Haniger to a three-year, $43.5 million contract (December 2022)
The Giants are known more for their swings-and-misses in free agency than making a big deal they would later regret, so you have to scramble a bit to find a clear worst mistake. The Brandon Crawford two-year, $32 million extension resulted in negative WAR. It's too early to call the Jung Hoo Lee signing a bust, but the early returns before he went down with a season-ending injury weren't great.
For now, we'll go with the Haniger signing, if only because it also didn't make sense at the time. Haniger was an injury-prone right fielder with below-average speed coming off a season in which he played just 57 games -- and was entering his age-32 season. That's the perfect trifecta of risk: injuries, lack of speed and 30-something. A good general rule to follow: Never sign a slow right-handed hitter in his 30s unless he's absolutely elite at the plate. The next mistake on our list fits that billing as well.
27. Miami Marlins
Biggest mistake: Signing Avisail Garcia to a four-year, $53 million contract (December 2021)
Like with the Pirates, I would have expected a few more colossal blunders for a team with so few winning seasons. (The Marlins have finished above .500 only twice since 2009, and one of those was the shortened 2020 season.) Like the Pirates, the Marlins never spend big bucks in free agency -- except the one time this decade they did, it was to give Garcia the fourth-largest free-agent contract in Marlins history. Talk about punching yourself in the face. How bad was Garcia? Arguably the worst player in baseball over the past three seasons. (He still has one year left on the deal, but the Marlins released him last June.) Garcia ranks eighth worst in cumulative WAR among position players since 2022 -- and that's only because he didn't play enough to rank lower. That this deal would end poorly was no surprise: Garcia had been inconsistent throughout his career and, given that he swung at everything between home plate and Mars, was unlikely to age well.
26. Atlanta Braves
Biggest mistake: Trading William Contreras to the Brewers (December 2022)
No organization has made more important positive moves this decade than the Braves, from drafting Spencer Strider in the fourth round to locking up their young players to long-term deals to acquiring Chris Sale from the Red Sox. You could argue they messed up the Freddie Freeman negotiations when he became a free agent, but they moved quickly in trading for Matt Olson and signing him to an eight-year extension.
For Atlanta's biggest mistake, let's go with the Contreras trade, part of a three-team transaction with the Brewers and A's. Contreras had made the All-Star team with the Braves in 2022, but they didn't believe in his defense, so they acquired Sean Murphy from Oakland for an upgrade behind the plate. Murphy had a great first half in 2023 but hasn't hit since then, whereas Contreras has proved more than adequate at catcher and finished fifth in the MVP voting in 2024. He leads catchers in WAR over the past two seasons. This won't look so bad if Murphy rebounds, but for now, it reads as a rare misevaluation by the Braves.
25. Houston Astros
Biggest mistake: Signing Jose Abreu to a three-year, $58.5 million contract (November 2022)
Coming off a World Series title in 2022, the Astros parted ways with GM James Click. Owner Jim Crane, now calling the shots, decided they needed a first baseman to replace Yuli Gurriel. He wasn't wrong! But few deals have gone south as fast as this one as Abreu hit .237/.296/.383 in 2023 and then got released after playing just 35 games in 2024 and hitting .124. Was Abreu's rapid fall foreseeable? He was entering his age-36 season but was coming off a good season with the White Sox in 2022 -- and most reviews of the signing were favorable, believing Abreu would be useful for at least a season or two. In the end, however, his Houston tenure looked like this: 176 games, negative WAR and two exits from the playoffs when offense from first base would have helped.
24. Cincinnati Reds
Biggest mistake: Signing Mike Moustakas to a four-year, $64 million deal (December 2019)
The Reds never, ever spend in free agency. In fact, before signing Moustakas and Nick Castellanos to matching $64 million contracts before the 2020 season, their biggest free agent contract had been a $46 million deal with reliever Francisco Cordero way back in 2008. But owner Bob Castellini got antsy and decided the team had a chance to win with a couple of power hitters.
Indeed, the Reds did make the playoffs in the shortened season of 2020 -- but only because of the expanded 16-team format. They promptly got shut out in two losses to the Braves in the wild-card series. Moustakas wasn't that good in 2020 (0.2 WAR in 44 games), but the signing was even more odd considering Cincinnati signed him to play second base. Even at the time, a 31-year-old third baseman moving up the defensive spectrum certainly didn't seem like a good idea. Moustakas couldn't stay healthy and his time with the Reds produced minus-1.6 WAR. For a team like the Reds, flushing $64 million down the sewer is a fiasco. Meanwhile, Castellanos opted out of his deal after two seasons and the Reds were back to rebuilding.
23. St. Louis Cardinals
Biggest mistake: Trading Randy Arozarena to the Rays (January 2020)
Some of the Cardinals' struggles the past two seasons can be traced back to the 2019-20 offseason. First, they sent Adolis Garcia to the Rangers for cash considerations. Then they traded Arozarena to the Rays, with pitching prospect Matthew Liberatore the primary return. The Cardinals had been successful for so long in large part due to their successful evaluation of their own players. These were two big misses.
With Garcia, you can at least understand why the Cardinals gave up on him: He was 26 years old and had posted a .301 OBP in Triple-A (although with 32 home runs). Arozarena, however, had hit .344/.431/.571 between Double-A and Triple-A and was two years younger. It was clear he could hit. Over the ensuing five seasons, those two have combined for three All-Star appearances, a whole bunch of home runs and a lot of postseason heroics. Cardinals outfielders, meanwhile, ranked 25th in the majors in OPS in 2024 and 19th in 2023.
22. Chicago Cubs
Biggest mistake: Non-tendering Kyle Schwarber (after 2020 season)
It's still a little sad how that great young core of position players on the 2016 Cubs -- one that was supposed to lead to a dynasty -- all drifted away, even if the Cubs made the right decision on letting those players go or trading them. Except for Schwarber. He's the one player in the group who should have remained a lifelong Cub.
After hitting .188 in the COVID-shortened season of 2020, the Cubs didn't offer Schwarber a contract for 2021. It didn't make sense at the time. Why read into anything that happened that year? The Cubs haven't made the playoffs and have been searching for a power hitter ever since. Schwarber ranks third in the majors in home runs and ninth in runs since the Cubs let him go, becoming a cult hero in Philadelphia in the process. He should be doing that for the Cubs -- who haven't had a player hit 30 home runs in the past four seasons.
21. Kansas City Royals
Biggest mistake: Waiving Brent Rooker (November 2022)
The Royals had acquired Rooker from the Padres in August for third-string catcher Cam Gallagher, although they gave Rooker just 29 plate appearances the rest of that 2022 season. He didn't do anything to impress and the Royals -- who lost 97 games that year -- apparently had 40 better players to protect on the 40-man roster.
Of course, they didn't have 40 better players. This was just one of those cases where a player unexpectedly explodes after getting released. That happens more often with pitchers, where a new pitch or a new grip can do wonders, but rarely with position players. All Rooker has done the past two seasons with the A's is mash 69 home runs, make an All-Star team and finish 10th in the MVP voting in 2024 after producing 5.6 WAR.
20. Tampa Bay Rays
Biggest mistake: Pulling Blake Snell in the sixth inning of Game 6 of the World Series (October 2020)
Any in-game decision has four ways it can go:
1. Right process, right result
2. Right process, bad result
3. Bad process, right result
4. Bad process, bad result
It's the fourth one that gets managers fired -- see Grady Little leaving in an obviously fatigued Pedro Martinez in Game 7 of the 2003 ALCS. When manager Kevin Cash pulled Snell after 73 pitches with one out in the sixth inning and watched the Rays eventually lose a 1-0 lead and the World Series, the ensuing uproar and second-guessing mostly ignored that Cash had followed the right process.
After all, that season Snell had allowed a .618 OPS through 50 pitches; after 50 pitches, it was .885. Yes, he was dealing -- he had just allowed his second hit and had nine strikeouts -- but Mookie Betts and Corey Seager were coming up and Snell was already well past that 50-pitch total.
"The only motive was that the lineup the Dodgers feature is as potent as any in the league," Cash said after the game. "Personally, I felt Blake had done his job and then some. Mookie coming around the third time through ... I value that."
The issue, however, was that Cash brought in Nick Anderson -- who had allowed a run in six consecutive appearances that postseason -- to replace Snell. With fewer off days due to the expanded playoffs, Anderson was also pitching on fumes yet was asked to get out the two best hitters on the Dodgers. He couldn't do it. Betts tied the game with a double, and, after a wild pitch, Seager knocked in Betts with the go-ahead run. The Dodgers won 3-1 to clinch the title -- and Snell was traded that offseason to the Padres.
19. Toronto Blue Jays
Biggest mistake: Pulling Jose Berrios in the fourth inning of the wild-card series (October 2023)
We could have gone with the Hyun Jin Ryu signing (four years, $80 million), a deal that produced just two healthy seasons, but I'm pretty sure Blue Jays fans would go with manager John Schneider's decision to remove Berrios in that playoff game -- a similar move to the Snell one except even harder to rationalize since it came in the fourth inning and Berrios had thrown just 47 pitches. What made it even worse was that Twins manager Rocco Baldelli totally played Schneider.
The situation: It was 0-0 in a must-win Game 2 for the Blue Jays, so the urgency was at least understandable. Berrios walked Royce Lewis to lead off the inning, and with three of the next four batters hitting from the left side, Schneider brought in lefty Yusei Kikuchi to replace Berrios. Baldelli promptly pinch hit three right-handed batters and the Twins scored two runs -- the only runs in a 2-0 victory. The bigger message here, however, was that Schneider didn't trust his pitcher. Blue Jays players certainly didn't like the move, with Whit Merrifield saying afterward "I hated it" and Vladimir Guerrero Jr. adding "everybody was surprised." Maybe it wasn't a surprise the Jays fell apart in 2024.
18. New York Yankees
Biggest mistake: Bringing in Nestor Cortes in relief in Game 1 of the World Series (October 2024)
OK, we have our third straight BIG DECISION in the postseason that backfired. This ranks as the most egregious of the three for the obvious reason: Cortes hadn't pitched in more than a month, last appearing in a game in the regular season Sept. 18 before manager Aaron Boone called him out of the bullpen in the bottom of the 10th inning on Oct. 25. Before Cortes even threw a pitch, Yankees fans I know were texting things like "WHAT IS BOONE DOING?!?!" and "GAME OVER."
Again, the thinking was clear: Jake Cousins had allowed two batters to reach with one out, with who else but Shohei Ohtani, Mookie Betts and Freddie Freeman coming up. There was no good decision to make unless you had Mariano Rivera warming up, and there was no Mariano Rivera around this evening. Ohtani and Freeman both had sizable platoon splits, so bringing in a left-hander was the move. Boone even got bailed out when Cortes retired Ohtani on a foul pop to left field. As Alex Verdugo tumbled into the stands to make that catch, the runners moved up a base -- allowing Boone to intentionally walk Betts to set up another lefty-lefty matchup. We know what happened then: Freeman's game-winning grand slam, one of the great moments in World Series history.
In retrospect, the bigger mistake -- as Boone himself alluded to -- was not bringing Luke Weaver, his best reliever, back to pitch the 10th inning. He had thrown just 19 pitches, so he could have gone another inning. Boone had also burned through Clay Holmes and Tommy Kahnle with just a combined 13 pitches. He could have used lefty Tim Hill, who had been effective in the playoffs. Instead, he brought in a starter who hadn't pitched in more than a month.
17. New York Mets
Biggest mistake: Signing Max Scherzer ... and Justin Verlander ... and then going 75-87 (2023)
No franchise has had a more volatile half-decade than the Mets. They've shuffled through five general managers/presidents of baseball operations (although David Stearns should now be here for the long haul); they've employed four managers (including Carlos Beltran, who was fired before ever managing a game); and Steve Cohen bought the team in that span as well. Along the way, they've zigged and zagged from 77-85 (2021) to 101-61 to 75-87 to 89-73.
Their biggest mistake might very well end up being trading Pete Crow-Armstrong to the Cubs for two months of Javier Baez for an ill-fated run at the postseason in 2021. Crow-Armstrong looks as if he might turn into a Kevin Kiermaier-type center fielder who wins Gold Gloves and produces enough offense to make him extremely valuable. Until that happens, however, we'll turn to the attempt to purchase a pennant in 2023. The Mets had signed Scherzer in 2022 to a three-year contract, and he had an outstanding season. Then they doubled down with Verlander for the 2023 season, giving him a two-year deal that matched Scherzer's $43.33 million as the highest average salary at the time. Throw in a bunch of other big contracts that winter and the Mets blew away the previous record for largest payroll.
And the team stunk. Scherzer and Verlander weren't so horrible, but the Mets were out of the race come July. Give them credit, though: They made the decision to pivot away from the pair at the trade deadline. They got some prospects in the two trades, and that allowed them to rejigger things for 2024 -- a season that ended in the NLCS. (Neither Scherzer nor Verlander, still on those Mets contracts, was useful in 2024. So, if New York had kept them, it likely would have been another bad season.)
16. Milwaukee Brewers
Biggest mistake: Trading Josh Hader away at the trade deadline (August 2022)
This is a hard one to rank because the Brewers made out OK in the trade, which included acquiring Esteury Ruiz, who was later flipped to the A's in the William Contreras trade (the Brewers also got reliever Joel Payamps in that deal). Still, this trade also backfired in a huge way. At the time of the deal on Aug. 1, the Brewers were in first place in the NL Central, three games up on St. Louis. Maybe the front office believed there was enough cushion there. Maybe they believed they were good enough to win without Hader. Maybe they thought Devin Williams would be enough at the back of the pen. The idea: Trading Hader now, rather than in the offseason, meant a team would have him for two potential playoff runs and the Brewers could thus get more for him.
"Today's trade is about doing everything we can as an organization to continue our mission and our goal of giving our team as many bites at the apple as we possibly can," David Stearns, then the Brewers' president of baseball operations, said. Except the team collapsed. Taylor Rogers, part of the return from the Padres, had a 5.48 ERA with the Brewers and lost three games. The Brewers went 29-31 after the trade, and the Cardinals surged past them to win the division. The Brewers missed the playoffs. There was no apple to bite in 2022.
15. Seattle Mariners
Biggest mistake: Signing Robbie Ray ... and then using him against Yordan Alvarez (2022)
Most of Seattle's mistakes have been of the minor variety -- bringing in veterans who promptly struggle to hit in the Seattle dungeon. Ray was a bigger mistake with multiple ripple effects. The initial signing was met with mixed reviews: Ray got five years and $115 million, although he was coming off that Cy Young Award with the Blue Jays. Although he deserved the honor, leading American League pitchers in ERA, strikeouts, innings and WAR, it seemed likely that regression was in order as he had allowed 33 home runs.
His 2022 season with Seattle was OK: 12-12, 3.71 ERA. The Mariners ended a long playoff drought and beat the Blue Jays in the wild-card series (although Ray got knocked out early in his start). Then came Game 1 of the ALDS in Houston. The Mariners led 7-5 entering the bottom of the ninth. Paul Sewald hit a batter and allowed a two-out single, bringing up big, bad Alvarez. Manager Scott Servais turned to Ray, setting up a lefty-lefty matchup. On paper, that made sense, but I'm never a fan of using a pitcher in a role he's unaccustomed to. Sure enough, two pitches later, Alvarez crushed a walk-off three-run home run.
In 2023, Ray made just one start and blew out his elbow. The Mariners missed the playoffs by one win. They traded him for Mitch Haniger, in an exchange of bad contracts. Haniger hit .208 with minus-0.2 WAR in 2024. The Mariners, once again, missed the playoffs by one win. They need offense for 2025 but haven't signed any free agents -- in part because Haniger is still making $15.5 million.
14. Arizona Diamondbacks
Biggest mistake: Signing Madison Bumgarner to a five-year, $85 million contract (December 2019)
The Diamondbacks haven't had much luck with free agent pitchers. They gave Zack Greinke a record-setting six-year deal ahead of the 2016 season, but then decided they could no longer afford him after three seasons. They signed Jordan Montgomery and Eduardo Rodriguez last offseason, which certainly didn't work out, at least in 2024. Between those, they signed Bumgarner. Let's hope this winter's signing of Corbin Burnes fares better.
Bumgarner went 15-32 with a 5.23 ERA in three-plus seasons with Arizona, making it through just four starts in 2023 before he was released, a sad ending to a wonderful career. There were some concerns about this signing right from the start, even though Bumgarner had been solid in 2019, with 2.9 WAR and 203 strikeouts in 207 innings. From 2017 to 2019, however, he had a 2.67 ERA in San Francisco and 4.61 on the road. Given those splits, there was little reason to expect him to be as good without the benefit of such a pitcher-friendly home park.
13. Philadelphia Phillies
Biggest mistake: Using Craig Kimbrel with their season on the line ... multiple times (October 2023)
Look, it's easy to second-guess decisions in the playoffs when they don't work out. But this was one where everyone was second-guessing even before the playoffs began. Kimbrel had an up-and-down regular season with the Phillies, posting a 3.26 ERA and striking out 94 in 69 innings but also allowing 10 home runs, losing six games, and blowing five saves in 28 chances (including his final two opportunities in September). The big question heading into the postseason: Were the Phillies willing to live and die with Kimbrel?
Well, we know the outcome. In Game 3 of the NLCS against the Diamondbacks, Kimbrel entered a 1-1 game in the bottom of the ninth. He walked the leadoff hitter. With one out, he walked light-hitting Geraldo Perdomo to load the bases. Ketel Marte singled in the winning run. The next day, manager Rob Thomson brought in Kimbrel to protect a 5-3 lead in the eighth inning. Alek Thomas tied the game with a two-run homer, and then a single and hit batter led to the go-ahead run. The Phillies did head back to Philadelphia needing just one win to reach the World Series. They didn't get it.
12. Minnesota Twins
Biggest mistake: Going all-in at the trade deadline in 2022 (Aug. 2, 2022)
The Twins were in first place in the division as the final day of the trade deadline began, with a one-game lead over the Guardians and three games over the White Sox. The front office decided it needed to make some moves -- multiple moves. In a frantic wave of trades, president of baseball operations Derek Falvey and general manager Thad Levine acquired Jorge Lopez, Tyler Mahle, Michael Fulmer and Sandy Leon in four different transactions.
The problem wasn't going for it but the poor results that followed. The Twins collapsed in September, going 11-22 and finishing under .500. The players they acquired contributed 0.2 WAR the rest of the way. Now look at the list of prospects they traded away: Yennier Cano, Cade Povich, Spencer Steer, Christian Encarnacion-Strand, Sawyer Gipson-Long and Ian Hamilton. No big stars there, but some decent players who would have improved the Twins the past two seasons.
11. San Diego Padres
Biggest mistake: Starting Dylan Cease on short rest in Game 4 of the NLDS (October 2024)
Look, there is little doubt most of those long-term contracts the Padres have committed to aren't going to end well -- Xander Bogaerts, Manny Machado, Fernando Tatis Jr. and so on, not to mention the Yu Darvish, Joe Musgrove and Jake Cronenworth deals. We'll let those sort themselves out later. For now, the decision to start Cease against the Dodgers in the playoffs was an easy call.
As with the Mariners and Ray, the Padres put a player in a position he's not used to. You can guess how many times Cease had started on three days' rest in his career. Yep: Zero. The postseason track record for pitchers starting on short rest isn't that good (4.24 ERA over the past 10 postseasons, understanding that only the top pitchers are generally used in those circumstances). Plus, the Padres were up in the series. There was no reason to take an unconventional risk. Yes, manager Mike Shildt still had Darvish on regular rest to start Game 5 and didn't have a great option for his fourth starter -- but win Game 4 and you don't need a Game 5. Lose, and you still have Cease to start Game 5. Cease gave up three runs and got knocked out in the second inning, and the Padres lost 8-0.
Maybe in the end it didn't matter: The Padres got shut out the final two games. Blame the bats. But I'd like to see what happens in the alternate universe where Cease doesn't start.
10. Los Angeles Dodgers
Biggest mistake: Trading for Lance Lynn ... and then starting him with the season on the line (2023)
If we had done this list for the previous decade, the Dodgers may have ended up with the No. 1 biggest mistake: Trading Yordan Alvarez to the Astros for reliever Josh Fields. While they haven't made any blunders of that magnitude in the 2020s, their handling of their rotation in 2023 was a disaster. The Dodgers won 100 games, but as you might remember, had injury concerns up and down the rotation. Their idea for help: Acquiring Lynn, who had a 6.47 ERA for the White Sox and had allowed 28 home runs in 119 innings.
With the Dodgers, Lynn continued to get hammered, coughing up 16 more home runs in just 64 innings. Yet come the playoffs, and down 0-2 to the Diamondbacks in the NLDS, Dave Roberts gave Lynn the ball in Game 3. He gave up four home runs -- in one inning. The Dodgers lost 4-2 and went home. At least Roberts learned a valuable lesson: Faced with a similarly depleted rotation in 2024 and facing elimination against the Padres in Game 4 of the NLDS, he went with a bullpen game rather than a bad starter. The Dodgers won -- and the rest is history.
9. Chicago White Sox
Biggest mistake: Hiring Tony La Russa as manager (October 2020)
More than anything, this move symbolizes the dysfunction of the White Sox going back to the 2010s. In 2020, the White Sox made the playoffs with their first winning season since 2012 (going 35-25 in the shortened season). Following a quick exit in the wild-card series, owner Jerry Reinsdorf then decided he needed to rectify what he called the biggest mistake of his career: firing La Russa as White Sox manager in 1986. So he hired La Russa even though he hadn't managed since 2011. Yes, the White Sox did win the division in 2021, but based on reporting at the time, that seemed as much spite of La Russa as because of him. They lost in the first round of the playoffs, and then everything started falling apart in 2022, with La Russa stepping down in August because of health concerns.
8. Detroit Tigers
Biggest mistake: Signing Javier Baez to six-year, $140 million contract (December 2021)
The Tigers had spent four miserable years rebuilding, and after going 77-85 in 2021, they thought it was time to make a push, so then-GM Al Avila signed Baez and Eduardo Rodriguez as free agents. Baez was 29 years old and had obvious deficiencies in his game: He led the National League with 184 strikeouts in 2021 while walking just 28 times. Still, he had hit 31 home runs and played good defense, so there was hope his power and D would carry him through the contract.
It was a risky bet at the time, and Baez hit just .238 with a .278 OBP and 17 home runs in 2022. The Tigers lost 96 games, and Avila was fired as GM. Baez has been even worse at the plate since then. He missed part of 2024 with an injury and has probably lost his job to Trey Sweeney. In retrospect, Baez's plate discipline was only going to become more problematic as his bat slowed up, plus most players start declining defensively in their late 20s, so it's never a good idea to bet on a player to remain at a high defensive level later in his career. Baez looks unplayable at this point -- with three years remaining on the deal.
7. Cleveland Guardians
Biggest mistake: Trading Junior Caminero to the Rays (November 2021)
Given their payroll limitations, the Guardians make as many good moves as any team, but this one harkens back up to the original list in the intro, a deal that could end up haunting the Guardians much as the Alvarez deal haunts the Dodgers (except Cleveland hasn't won two World Series titles this decade).
Caminero had just completed his first season of pro ball, hitting .295 with nine home runs in the Dominican Summer League. He wasn't a top prospect -- he didn't crack Baseball America's top 30 Rays prospects entering 2022 -- when the Guardians decided to deal him for pitcher Tobias Myers. Give credit to the Rays for this one. Myers didn't even make it through July 2022 with the Guardians, who traded him to San Francisco. Caminero, meanwhile, broke out in the minors in 2023 and emerged as one of the top prospects in the game. After a 43-game cameo with the Rays in 2024, he's ready for his first full season in the majors. If he reaches the stardom many are predicting, this mistake could end up as one of the most memorable of the decade.
6. Texas Rangers
Biggest mistake: Trading Emmanuel Clase to Cleveland (December 2019)
The Rangers have two trades to consider for this spot. First is the Clase deal. He debuted with the Rangers in 2019 and posted a 2.31 ERA in 23 innings, throwing that 99 mph cutter. So, they knew what they had, or should have known. They traded him for Corey Kluber, who was coming off an injury and would pitch just one inning for Texas before getting injured again and heading off into free agency.
The other deal is the Cole Ragans-for-Aroldis Chapman trade in 2023. Usually, trading for a rental reliever only costs a team a Single-A pitching prospect or two, the type of flyer who usually doesn't make it. In this case, however, Ragans was already in the majors, pitching in relief, although not particularly well (5.92 ERA). Ragans went to the Royals and immediately turned into one of the best starters in the majors, following up with an outstanding 2024.
Bottom line: The Rangers just blew it both times, and there's nothing more damaging than missing on a young, controllable player. But I have to go with the Clase deal, who has a chance to go down as one of the best closers of all time, with a 1.67 career ERA so far. Plus, Chapman did help the Rangers win the 2023 World Series, picking up six holds in the postseason. Flags fly forever.
5. Colorado Rockies
Biggest mistake: Signing Kris Bryant to a seven-year, $182 million contract (March 2022)
You knew the Rockies were going to rank high; it was just a matter of whether to go with the Bryant signing or the Nolan Arenado trade. Look, the Arenado trade was a debacle. The only value they've received from it has been Austin Gomber, who has 3.9 WAR in four seasons with the Rockies. The Rockies even helped pay down some of Arenado's contract. But the Bryant deal has been even worse than that.
Yes, Bryant has battled injuries all three seasons in Colorado and played just 159 games, so maybe you can consider this bad luck. OK, sure. But this had "bad idea" written all over it from the beginning, considering Bryant had already suffered a string of injuries, including a major shoulder injury in 2018. But even more problematic and just as obvious was that Bryant's batted-ball metrics weren't impressive. His average exit velocity in 2021 was in just the 29th percentile -- which had been an improvement over the previous three seasons. His defense metrics had also declined. He was turning 30. It was pretty easy to see at the time that Bryant wasn't worth $182 million.
4. Boston Red Sox
Biggest mistake: Trading Mookie Betts to the Dodgers (February 2020)
The Red Sox have made some major blunders this half-decade: They traded Chris Sale last offseason and watched him win the National League Cy Young Award with Atlanta; the Trevor Story and Masataka Yoshida contracts haven't paid dividends; even Rafael Devers' $313 million extension feels excessive. But the decade began with the Betts trade in February 2020, kicking off a five-year stretch when the Red Sox have mostly wandered in the wilderness, with three straight non-winning seasons following a lone playoff appearance in 2021.
At the time of the trade, the Red Sox were in cost-cutting mode after running the highest payrolls in the sport in 2018 (when they won the World Series) and 2019 -- remember dumping David Price's contract was a key part of the deal. They were also uncertain of their ability to sign Betts, who had one year left before free agency. Perhaps they misread their superstar player, however. On former teammate Brock Holt's podcast in 2023, Betts said, "I know people don't believe it, but I wanted to stay in Boston my whole career. That was my life. I knew everybody there. It was a short flight to Nashville. It was perfect." Betts would sign a 12-year, $365 million extension with the Dodgers -- a huge contract at the time, but given Betts' sustained level of excellence, it now looks like a bargain. Betts told Holt that he would have signed the same deal to remain in Boston.
As for the trade itself? Meh. Alex Verdugo was OK in his four seasons with Boston, averaging about 2.0 WAR per year. Connor Wong has developed into the team's regular catcher the past two seasons. Jeter Downs never made it. Meanwhile, the Red Sox have committed more than $543 million to Devers, Story and Yoshida. Maybe they could have afforded Betts after all.
3. Washington Nationals
Biggest mistake: Signing Stephen Strasburg to a seven-year, $245 million contract (December 2019)
Sorry, no injury mercy here. Coming off their run to the 2019 World Series title -- with Strasburg carrying the team on his back with an epic postseason (5-0, 1.98 ERA) -- the Nationals acted a little too emotionally and gave Strasburg what still ranks as the third-largest deal ever for a pitcher. While he had been healthy in 2019, this deal had "red flag" written all over it at the time, considering he had missed parts of the previous four seasons. Strasburg would win just one game during the new contract before finally officially retiring in April.
To make matters worse, Strasburg's inability to pitch set off a domino effect that led to one of the worst trades of the decade. With the Nationals struggling in 2021 without Strasburg, they traded Max Scherzer and Trea Turner to the Dodgers, a deal that should have netted the Nationals a huge return, especially since Turner still had another season left until free agency. The return? Keibert Ruiz and Josiah Gray. That led to the Juan Soto trade the following season (which at least has a chance to work out better for the Nationals).
2. The Athletics
Biggest mistake: The post-lockout fire sale (March 2022)
We really shouldn't even classify this as a mistake. This was intentional self-destruction, from an owner who doesn't care about winning and was willing to sacrifice any last remnants of hope the team would stay in Oakland. In a matter of five days, beginning two days after the end of the MLB lockout, the team traded away starting pitcher Chris Bassitt and then All-Stars Matt Olson and then Matt Chapman. That was the week you knew the glorious history of the A's in Oakland would come to an end. A couple weeks later, the A's also traded Sean Manaea.
Of course, we're cheating a bit here by grouping a series of trades together, but forced into these deals by the team owner, the front office also failed to deliver. The return for all of these players: J.T. Ginn, Adam Oller, Ryan Cusick, Joey Estes, Shea Langeliers, Cristian Pache, Zach Logue, Kevin Smith, Kirby Snead, Gunnar Hoglund, Adrian Martinez and Euribiel Angeles. Stop me when you get excited. OK, Shea Langeliers has developed into a nice catcher. Still, the overall net value so far for these players while with the A's: 0.4 WAR (Langeliers has been worth 4.1 WAR, so the rest of the group has collectively been well below replacement level). I guess the biggest return did come for John Fisher: a move out to Las Vegas.
1. Los Angeles Angels
Biggest mistake: Keeping Shohei Ohtani at the trade deadline (2023)
Arte Moreno didn't want to be known as the owner who traded away Ohtani. Instead, he'll go down as the owner who couldn't win with Ohtani (and Mike Trout). Moreno would rationalize the trade deadline decision as doing what was best for the fans. "From a fan perspective, they pay for tickets and watch the games and listen to the games, this is a special guy," Moreno said the following spring. "I'd like to see him play. We're in the entertainment business. We made a decision, a group decision, that the best thing was to keep him and make a run."
When word leaked on July 26 that the Angels had decided not to trade Ohtani, they were seven games out of first place. According to FanGraphs, they did have playoff odds of 16.7% -- maybe, with a little luck, they could win a wild card. Remember, Ohtani hadn't yet blown out his elbow. He would have brought the Angels a massive return in prospects, a chance to turn around a franchise that hadn't had a winning season since 2015. And the Angels seemingly had little chance of re-signing Ohtani as a free agent after the season. But the decision was made: They kept Ohtani, traded top catching prospect Edgar Quero for Lucas Giolito and Reynaldo Lopez, and made a couple other minor moves to augment their small chance at a playoff run.
Within a week, the Angels were out of it. They lost seven games in a row to begin August. Ohtani made one last abbreviated start on Aug. 23 before being shut down with a torn UCL. Giolito went 1-5 with a 6.89 ERA in six starts and was put on waivers. Lopez went 0-2 in relief. C.J. Cron hit .200 and Randal Grichuk hit .216. It wasn't a good team. The Angels finished 73-89.
And two months later, Ohtani signed with the Dodgers.