There are typically around two hundred trades every calendar year in Major League Baseball, and sometimes they hurt for years after the fact.
But which swaps from at least a year ago are most painful to this day?
All of these trades (with one noteworthy 2016 exception) happened between Jan. 1 2017, through Dec. 31 2022. At least one of the players the team wishes it hadn’t traded away still could have been under team control for the 2024 season.
A few examples of what doesn’t count: Baltimore trading away Manny Machado in 2018 a few months before he became a free agent; Boston trading away Mookie Betts in 2020 prior to his final year of arbitration eligibility; Miami trading away Christian Yelich in 2018, whose contract would have expired at the end of 2022. They may well still regret making those moves, but the teams would’ve lost those players (or had to pay a whole lot more to keep them) by now anyway.
But the Cubs sending both Eloy Jiménez and Dylan Cease to the White Sox in 2017? Both debuted in 2019 and won’t reach free agency until 2025, so that one definitely counts.
And St. Louis trading Adolis García for cash considerations? Yikes.
In each case, what the team actually got in return for the player(s) in question is crucial information, too. For instance, Arizona trading Jazz Chisholm Jr. to Miami for Zac Gallen in 2019 was hardly a regrettable move for either side. And while this one was a 2016 trade, the Cubs gave up Gleyber Torres (and more) for an Aroldis Chapman rental, but the southpaw closer ended up playing a gigantic role in Chicago breaking the 108-year curse, making Torres a more than acceptable sacrifice.
After the forthcoming unforgettable dishonorable mention, the collection of fleecings by Tampa Bay and the trio of quality trades made by San Francisco, trades will be presented in chronological order.
The Trade: Colorado Rockies send 3B Nolan Arenado and up to $51 million to St. Louis Cardinals for LHP Austin Gomber, 3B Elehurus Montero, RHP Tony Locey, RHP Jake Sommers and IF Mateo Gil
We’re only dubbing this one a dishonorable mention because it’s all but a foregone conclusion that Arenado would have opted out of his contract after either the 2021 or 2022 campaigns to get the heck out of Colorado. So, in theory, the Rockies wouldn’t have had him anyway.
He is still on the same eight-year contract in St. Louis that originally signed in Colorado. And because he opted in to the remainder of that contract, the Rockies are still paying him $5 million per year for each of the next three years—this after already paying basically his entire $15 million salary in 2021, more than $5 million in 2022 and $16 million in 2023.
And what did they get in return for handing the Cardinals an annual MVP candidate and offering to pay more than a quarter of his remaining contract?
A whole lot of nothing.
Three of the five players Colorado got back still have not made it to the majors, with two of them now playing in different farm systems. Montero made it to the bigs, but has a 0.0 bWAR in two seasons. And Gomber has made 83 appearances with a 5.22 ERA.
Since the trade, Colorado has gone 201-284 and has come to be regarded as the worst-run franchise in baseball—aside from maybe the Oakland/Las Vegas/Whatever Athletics.
An all-time disaster on so many levels.
Trade No. 1: Tampa Bay sends RHP Chris Archer to Pittsburgh Pirates for RHP Tyler Glasnow, RHP Shane Baz and OF Austin Meadows (July 31, 2018)
Trade No. 2: Tampa Bay sends OF Nick Solak to Texas Rangers for RHP Pete Fairbanks (July 13, 2019)
Trade No. 3: Tampa Bay sends LHP Matthew Liberatore, C Edgardo Rodriguez and 2nd round comp pick to St. Louis Cardinals for OF Randy Arozarena, OF José Martínez and 1st round comp pick (Jan. 9, 2020)
Trade No. 4: Tampa Bay sends RHP Tobias Myers to Cleveland Guardians for IF Junior Caminero (Nov. 19, 2021)
Trade No. 5: Tampa Bay sends OF Austin Meadows to Detroit Tigers for UTIL Isaac Paredes and 2nd round pick (Apr. 5, 2022)
At this point, it is an annual right of passage that Tampa Bay is going to outright rob somebody in a trade.
And, like, this isn’t even a comprehensive list. The Rays also got 2023 AL batting champ Yandy Díaz from Cleveland in the 2018 Edwin Encarnación three-team trade, got Manuel Margot for Emilio Pagán in 2020, acquired Jeffrey Springs from the Red Sox in 2021, got Shawn Armstrong for cash considerations in 2021 and traded for both Luke Raley and Harold Ramirez in the spring of 2022, giving up next to nothing in any of those swaps.
It’s baffling that teams are still willing to negotiate with the Rays.
Of the bunch, the Glasnow/Archer trade most often gets brought up as a huge fleecing, but the three most recent deals might be even worse for the teams that met Tampa Bay at the negotiating table.
There’s still hope in St. Louis that Liberatore will pan out, but thus far that Arozarena trade was a complete nightmare for the Cardinals.
Caminero is now regarded as one of the top prospects in all of baseball while Myers has bounced around the minors for four different teams and has nowhere near the same expected potential.
And getting Paredes and a draft pick for Meadows—who did not homer in two seasons with Detroit and who was originally part of the Archer swap—was an all-timer of a lop-sided trade.
Trade No. 1: San Francisco sends RHP Tyler Herb to Baltimore Orioles for OF Mike Yastrzemski (March 23, 2019)
Trade No. 2: San Francisco sends RHP Shaun Anderson to Minnesota Twins for 1B LaMonte Wade Jr. (Feb. 4, 2021)
Trade No. 3: San Francisco sends cash considerations to New York Yankees for IF Thairo Estrada (Apr. 11, 2021)
The third swap is nowhere near the most egregious cash/future considerations trade that will appear on this list, but what a trio of under-the-radar-at-the-time moves for the Giants, right?
Dating back to the beginning of 2021, Yastrzemski, Estrada and Wade rank second, fourth and fifth, respectively, on the Giants in total plate appearances with a combined total of 820 hits, 500 runs, 135 home runs and 65 stolen bases.
Per FanGraphs, they’ve been worth a combined 18.5 WAR over the past three years. And Yastrzemski was even better in 2019 and 2020 for San Francisco than he was from 2021-23.
For those nightly staples in the lineup, the Giants gave up a pitcher who has yet to reach the majors (Herb), a pitcher who has logged 24.1 MLB innings with an 8.88 ERA since the beginning of 2021 (Anderson) and those cash considerations.
Of San Francisco’s three trading partners here, Minnesota probably has the biggest regrets. But considering Wade hit .211 in his two brief stints in the majors with the Twins, it’s hard to blame them for giving up on a guy who they spent a ninth-round draft pick on six years before the trade.
The Trade: Houston Astros send RHP Josh Fields to Los Angeles Dodgers for OF/DH Yordan Álvarez
Had Houston not already signed Álvarez to a long-term extension, he still would have been arbitration-eligible in each of the next two seasons, making this the gift that keeps on giving.
It does bear mentioning that Josh Fields actually pitched fairly well for the Dodgers, giving them a 2.61 ERA and a 1.04 WHIP in his 2.5 seasons with the club. He wasn’t their first choice in high-leverage situations, but he did have four saves and 25 holds.
And it’s not like the Dodgers have exactly struggled without Álvarez, repeatedly winning the NL West, save for finishing one game behind the Giants in 2021.
Still, this has turned into one of the worst trades of all-time, and it is least partially to blame for Los Angeles’ repeated postseason flameouts.
While the Dodgers offense has hopelessly vanished in three of the last five NLDS, Álvarez merely has a career 1.209 OPS in 16 career games played in that round of the playoffs. Put his bat in the heart of LA’s lineup and there’s a good chance it at least averages better than 3.3 runs per game across the 2019, 2022 and 2023 NLDS.
Instead, he has repeatedly propelled the Astros to the ALCS while the Dodgers helplessly watch from home.
The Trade: Miami Marlins send Marcell Ozuna to St. Louis Cardinals for Sandy Alcántara, Zac Gallen, Daniel Castrano and Magneuris Sierra
Say this much for Ozuna’s time in St. Louis: He did at least play a huge role in the Cardinals winning the 2019 NLDS against Atlanta. Without his two solo home runs and productive 10th inning out in Game 4 of that series, the Cardinals lose without ever forcing a Game 5.
But for two years of an outfielder who hit .262/.327/.451 while producing 4.7 bWAR, St. Louis gave up what have become two of the best starting pitchers in baseball today.
In fairness to the Cardinals, Gallen was never a top-tier prospect, and Alcántara hadn’t pitched particularly well in the minors in either 2016 or 2017. In fact, Sierra was the highest-rated prospect in the deal, even hitting .317 in 64 plate appearances for the Cardinals that season before never amounting to anything again.
But Alcántara has been worth 19.5 bWAR and won the 2022 NL Cy Young while Gallen has been worth 17.0 bWAR and was a top-10 finisher in the NL Cy Young vote in three of the past four years.
Alcántara signed a five-year deal with the Marlins, but he still would have been arbitration-eligible this season. Gallen has two years left before he hits free agency.
What really makes this one sting is how atrocious St. Louis’ starting pitching was in 2023, and how much they had to spend on veteran arms this offseason in hopes of cobbling together a respectable rotation in 2024.
The Trade: Chicago Cubs send RHP Dylan Cease, OF/DH Eloy Jiménez, IF Bryant Flete and IF Matt Rose to Chicago White Sox for José Quintana
Let’s start this one with what the Cubs thought they were getting in the deal.
José Quintana had been worth 21.2 bWAR in his first 5.5 years in the majors with the White Sox. He was only an All-Star in one of those seasons (2016), but FanGraphs had him rated as the 11th-best pitcher in the majors from 2012-16—tied with Stephen Strasburg, marginally ahead of Madison Bumgarner. Dude was solid.
Moreover, the five-year, $26.5 million contract that Quintana signed with the South Siders in 2014 included a pair of $10.5 million club options for 2019 and 2020. So they thought they were getting a borderline top-10 pitcher for 3.5 years at a total price of about $33 million.
Had he delivered at that level on the North Side, this deal wouldn’t have looked particularly bad in hindsight.
At any rate, you can kind of understand why the Cubs were willing to give up Cease and Jiménez, otherwise known as their top two prospects.
But Quintana simply was not the same pitcher for the Cubs, struggling to keep the ball in the yard and posting a mediocre 4.24 ERA over the course of his 82 appearances. (Not including his two starts in the 2017 NLCS, in which he had a disastrous 10.29 ERA.)
Now, Cease has blossomed into the borderline top 10 starter that Quintana used to be, while Jiménez has a career .275 batting average and has been reasonably valuable, when healthy.
From afar, it would be kind of funny if the Cubs double down by giving up another few quality prospects to re-acquire Cease, who is very much on the trade block these days.
The Trade: Seattle sends RHP Pablo López, OF Brayan Hernandez, RHP Brandon Miller and RHP Lukas Schiraldi to Miami for RHP David Phelps
What’s interesting in the aftermath of this one is that López wasn’t even the one Seattle was worried it might regret giving up. Hernandez was viewed as the headliner of the trade, a 19-year-old who was regarded as one of the top international signings of 2014-15.
He never came close to making it to the majors. Neither did Miller nor Schiraldi.
López sure did, though, blossoming into a borderline ace who Minnesota deemed worthy of giving up a reigning batting champ to acquire one year ago. And he was lethal in his first year with the Twins, tied with Blake Snell for the third-most strikeouts (234) in the majors this past season.
At the time of the trade, he was in high-A ball, saddled with a 5.04 ERA that year and still working to get back his velocity after undergoing Tommy John surgery in 2014.
No one knew what he would eventually become.
Nor did Seattle realize it was giving up four prospects for just 8.2 innings of mediocre relief work.
Phelps landed on the IL barely two weeks after arriving in Seattle, tried to come back two weeks later and ended up needing Tommy John surgery the following spring.
Part of the reason the M’s traded so much for him was because he was still arbitration-eligible for 2018. But he never pitched for them that season.
Seattle was hopelessly out of the AL West race (15.5 GB) when it made this trade, but it was only three games back in the wild-card hunt—and desperate to finally make the playoffs for the first time since 2001.
It went 30-36 the rest of the way, missing the postseason by 13 games before later needing to watch from afar as López became a star.
Bonus painful thought: Had the Mariners simply not made this trade, perhaps they never would have felt the need to invest $115 million in Robbie Ray.
The Trade: San Francisco sends OF Bryan Reynolds and RHP Kyle Crick to Pittsburgh Pirates for OF Andrew McCutchen
Those three previously mentioned trades the Giants made to upgrade their lineup?
They pretty much needed to hit all of those home runs to make up for this swing and a miss.
McCutchen had one $14.5 million season remaining before hitting free agency and was fresh off his seventh consecutive season with at least 21 home runs, 79 RBI and a .256 batting average. It made sense that a contender would want to trade for him as maybe the final piece of a championship puzzle.
But the Giants were fresh off a 98-loss mess of a 2017 campaign and made the bold decision to give up one of their top prospects (Reynolds) and a former first-round pick (Crick) to get one year of a 31-year-old McCutchen.
To his credit, McCutchen was fine. He ended up slightly below the aforementioned marks, going for 20 home runs, 65 RBI and a .255 batting average.
However, he got a chunk of those stats while with the New York Yankees, as the Giants—en route to 89 losses—traded him away at the end of August for two prospects who never amounted to anything.
Crick never amounted to much, either, but Reynolds has been a star in Pittsburgh with a career OPS of .830. The Pirates signed him to a long-term extension in April, buying him out of his final two years of arbitration eligibility and ensuring they won’t also need to trade him away at the age of 30/31.
The Trade: St. Louis sends Adolis García to Texas for cash considerations
We see trades for cash/future considerations all the time. In 2023 alone, there were 68 trades in which “We might help you out later” was all that one team gave up in the deal.
And for the vast majority of those pseudo purchases, the player doesn’t eventually become a major part of a World Series champion.
García is a rather large exception to that rule.
Though García clubbed 32 home runs at Triple-A Memphis in 2019, the reason St. Louis traded away the then 26-year-old Cuban star in the making was to make room for Kwang Hyun Kim on the 40-man roster. The Cardinals had to designate someone for assignment at that point, and they chose García. That meant they had seven days to either trade, release or place him on irrevocable waivers.
The silver lining is Kim was respectable, posting a 2.97 ERA in his 145.2 innings of work between 2020-21. He even got the start in Game 1 of the Cardinals’ wild card series against San Diego in 2020.
At least they didn’t waive García for a guy who gave them absolutely nothing.
However, the Cardinals would have passed on those 145.2 innings in a heartbeat if they had known García would average around 32 home runs and 99 RBI per year from 2021-23, or that he would hit five home runs against Houston in the process of becoming the 2023 ALCS MVP, en route to setting the MLB record with 22 RBI in a single postseason with a walk-off home run in Game 1 of the World Series.
The Trade: Oakland sends LHP Jesús Luzardo to Miami for OF Starling Marte
When Oakland made this trade—giving up a starting pitcher who was 5.5 years away from free agency for a two-month rental of a 32-year-old outfielder—perhaps it had already accepted that it was ‘now or never’ in advance of a massive rebuild. That week, the A’s also traded away a combined five prospects for Yan Gomes, Josh Harrison and Andrew Chafin, all of whom, like Marte, were slated for free agency at the end of the season.
And Marte did fare remarkably well in Oakland. He hit .316 with five home runs and 25 stolen bases, starting darn near every game in center over those final two months.
It wasn’t enough, though.
Oakland was six games behind Houston in the AL West and 4.5 games back in the wild-card race when it made the Luzardo/Marte swap, and it only got worse from there, going 30-30 to finish nine games behind Houston and six games out of the wild-card picture.
Despite that lackluster finish, at least it initially looked like an OK trade by Oakland. Luzardo had a 6.87 ERA for the A’s that season and wasn’t much better (6.44 ERA) in his 12 starts for Miami.
Over the past two seasons, though, Luzardo has been extremely valuable for the Marlins, and is now maybe the most coveted arm theoretically on the trade block with three years of arbitration eligibility still to come.
Would keeping Luzardo have kept Oakland from this dumpster fire of a rebuild? Almost certainly not.
But if they keep Luzardo and he pitches just as well in 2022-23, they would’ve been able to get so much more for him now than they did at the 2021 trade deadline.
The Trade: New York Mets send OF Pete Crow-Armstrong to Chicago Cubs for IF Javier Báez and RHP Trevor Williams
For the time being, this one hasn’t aged too poorly for the Mets.
Báez played some of the best baseball of his career down the stretch for New York in 2021, and he ended up getting a nine-figure contract from Detroit that offseason because of it. And Williams was a solid long reliever/spot starter for his season and a half in Queens, giving the Mets a 3.17 ERA over those 122 innings of work.
Even with Báez’s great play, though, the Mets completely collapsed in 2021. They were 55-47 and had a four-game lead in the NL East at the time of the trade, but they went 22-38 the rest of the way, missing the postseason by an inconceivable 11.5-game margin.
And to get those two veterans from the Cubs, New York gave up its first-round pick in the 2020 draft, which could be painful for years to come.
Crow-Armstrong was injured at the time, appearing in just six Single-A games in the entire 2021 season, but he has since blossomed into one of the highest-rated prospects in baseball, possibly slated to start in center for the Cubs on Opening Day.
The Mets do at least have a respectable outfield in Brandon Nimmo, Starling Marte and the newly acquired Harrison Bader and Tyrone Taylor, so they aren’t missing him in that regard. But if PC-A lives up to his potential and becomes a star in Chicago, New York will have to endure years’ worth of constant reminders of what could have been.
The Trade: Minnesota sends IF Christian Encarnacion-Strand, UTIL Spencer Steer and LHP Steve Hajjar to Cincinnati for RHP Tyler Mahle
Just about everything Minnesota did ahead of the 2022 trade deadline aged disastrously.
They sent four prospects to Baltimore (one of whom was Yennier Cano) for Jorge López, who blew the save in two of his first five appearances with the Twins and just wasn’t the same in those final two months. They also traded Ian Hamilton for Sandy León, getting 65 plate appearances with a .502 OPS for a pitcher who broke out this past season with the Yankees.
Worst of all, though, was the trade for Mahle.
The Twins were willing to give up quite a bit for Mahle, because he was also arbitration-eligible for 2023. But because of injuries, he made just nine starts between those two seasons with Minnesota, meaning the Twins gave the Reds their projected 2024 starting left fielder (Steer) and designated hitter (Encarnacion-Strand) for basically nothing.
It did seem like a great move at the time, though. Our Zach Rymer gave the Twins an A for acquiring what reasonably could have been the ace of the staff for 1.5 years and gave the Reds a B for getting a trio of prospects that MLB.com rated top 25 in Minnesota’s farm—none in the top six, though. ESPN’s David Schoenfield gave Minnesota an A- and Cincinnati a C.
Unfortunately, the Twins got drastically less out of Mahle than expected due to injury, and two of the three prospects they shipped to Cincinnati blossomed in a hurry.
And thanks in part to Mahle giving them very little, the Twins crashed and burned. They were six games above .500 with a one-game lead in the AL Central heading into 2022’s deadline day. They went 24-36 the rest of the way and lost the division by a 14-game margin.
Mahle signed a two-year deal with the Texas Rangers in December.
The Trade: Cleveland sends OF/1B Nolan Jones to Colorado for IF Juan Brito
Simply put, Cleveland was tired of waiting on Jones to finally deliver.
The Guardians spent a second-round pick on Jones in the 2016 draft and subsequently spent many years hoping he would finally become the star they thought he might be back when he was just an 18-year-old kid.
But it never happened.
They gave him a six-week-long taste of the big leagues in the summer of 2022 and he had two home runs and 31 strikeouts in 94 plate appearances.
So they gave up and sent him to the Rockies last season for a 21-year-old infielder with some long-term potential.
And while Brito did climb from High-A all the way to Triple-A this past season and might pan out nicely for the Guardians in short order, they sure could have used Jones’ bat in 2023.
Between his 39 games at Triple-A Albuquerque and his 106 games in Colorado, Jones hit 32 home runs and stole 25 bases, batting .314 and slugging .591. Meanwhile, Cleveland’s entire outfield hit 18 home runs in 2023, batting .250 and slugging .342.
Cleveland had the pitching to be a legitimate contender, but it just could not reliably score runs. And if you take what Jones did and plug it in place of what Will Brennan did for the Guardians in 2023, it’s plausible their entire season plays out differently.
[Also, miss me with your “Well of course Jones started hitting well in the high altitude of Colorado!” arguments, because he actually slugged better (.554) in road games than he did in home games (.530).]
