By admin 
The finishing touches of championship rosters can be built at the MLB trade deadline. It’s also where franchises can make a mistake that haunts them for years.
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Every year, front offices around baseball decide whether to buy at the deadline and add a missing piece to their lineup or pitching staff to make a postseason push. Others sell their coveted assets for a pile of prospects and aim to compete down the road.
As we approach the 2026 trade deadline at 6 p.m. ET Monday, here’s a look at the 10 biggest mistakes of the last 10 trade deadlines, dating back to 2016:
10. Reds let Luis Castillo go for peanuts (2022)
Mariners receive: Luis Castillo
Reds receive: Noelvi Marte, Edwin Arroyo, Levi Stoudt, Andrew Moore
This is the only deal on the list that involves the seller making the big mistake. Typically, selling teams are between a rock and a hard place at the trade deadline, and can’t be faulted for letting go of a player who will be on his next contract by the time they’re ready to contend. That wasn’t the case with the Reds and Castillo, though.
The right-handed starter was under team control through the 2023 season when he was shipped to Seattle. And while Cincinnati was in the middle of a 100-loss season in ’22, the Reds would rebound with an 82–80 record in ’23 and miss the playoffs by two games. None of the players they acquired for Castillo helped in the playoff chase, save for 35 games and 0.8 bWAR worth of production from Marte. Castillo, meanwhile, made his second straight All-Star team and finished fifth in AL Cy Young voting after racking up 219 strikeouts with a 3.34 ERA in 197 innings. He’s a genuine workhorse in the modern game, ranking sixth with 652 2/3 innings pitched since 2023.
Keeping their former ace could’ve pushed the Reds into the playoffs, and none of the prospects involved in this swap have panned out. Selling doesn’t always work out … though the next nine deals on this list may convince you it does.
9. Astros slip up en route to the World Series (2017)
Blue Jays receive: Teoscar Hernández and Nori Aoki
Astros receive: Francisco Liriano
On Aug. 12, 2016, Astros prospect Teoscar Hernández made his MLB debut and hit his first career home run off of Blue Jays pitcher Francisco Liriano. Less than a year later, they were traded for each other on July 31, 2017 as Houston loaded up on live arms ahead of what would become a World Series run.
Liriano was moved to the bullpen after the deal and pitched a total of 16 2/3 innings for Houston, recording a 4.32 ERA and grading out as below replacement-level in terms of bWAR (-0.2). He was also charged with a loss in Game 3 of the ALDS against the Red Sox and was not trusted in high-leverage situations thereafter. This was in the late stages of the veteran lefty’s career; he’d go on to pitch two more ho-hum seasons before retiring.
Hernández had only collected 100 career at-bats before the trade, but he almost immediately took off in Toronto, recording a .908 OPS in 26 games in 2017. He’d go on to hit 129 home runs for the Blue Jays over six seasons, earning two Silver Slugger awards and accumulating 10.6 bWAR.
The Astros may not care about losing this trade given the World Series title that followed, but Liriano did next to nothing for them and they could’ve used Hernández while they lost two of the next four World Series.
8. Padres get fleeced for Austin Nola, two relievers (2020)
Padres receive: Austin Nola, Dan Altavilla and Austin Adams
Mariners receive: Ty France, Andrés Muñoz, Luis Torrens and Taylor Trammell
In the middle of the strange 2020 season, the Padres put together one of the wildest trade deadlines of all time.
General manager A.J. Preller traded away 16 players and received 10 in return. Seven of those players were moved in San Diego’s deal with the Mariners, which was centered around 30-year-old catcher Austin Nola.
The brother of longtime Phillies pitcher Aaron Nola, Austin was a journeyman minor leaguer before debuting for Seattle in 2019. He got off to a nice start, logging a .796 OPS in 2019 and a .903 OPS in 29 games for the Mariners in ’20 before the trade. Pitchers figured him out pretty quickly in San Diego. Over 237 career games with the Friars, Nola logged a lowly .634 OPS and recorded just 2.6 bWAR over four years in San Diego. He was eventually sent down to the minors in ’23 as his struggles at the plate became untenable and only played in 14 more games in the majors, with the Rockies in ’25. He’s now a bullpen coach in Seattle.
Altavilla and Adams didn’t amount to much; the most notable part of either of their tenures with the Padres was Adams leading the majors with 24 hit batters in just 52 2/3 innings in 2021.
Ty France immediately started raking for the Mariners and recorded a .750 OPS over five seasons with them, and the former 34th round pick even made the 2022 American League All-Star team. But the best piece of the deal was Muñoz, who joins a long list of former Padres prospects to excel elsewhere. Muñoz began closing games for the Mariners in ’22. He was named an All-Star in ’24 and ’25, and in ’26 has recovered from a rough start to rank 12th in baseball with 19 saves. The Padres, meanwhile, broke the bank trading for closers Mason Miller (whom they probably should trade away soon) and Josh Hader in that same span.
7. Rays make a rare mistake (2021)
Rays receive: Nelson Cruz and Calvin Faucher
Twins receive: Joe Ryan and Drew Strotman
The Rays have remained competitive for the better part of two decades despite constantly ranking near the bottom of the league in payroll in part by regularly fleecing their trade partners. The Twins, however, undoubtedly got the better of this deal.
Cruz had long outran Father Time by maintaining his power stroke deep into his career, and had in fact made the All-Star team in 2021 at age 41 before the Twins traded him by the end of the month. But this swap essentially served as the end of Cruz’s days as an effective slugger. Cruz slashed .226/.283/.442 for the Rays over the rest of the 2021 campaign-and went 3-for-17 in the ALDS as the 100-win Rays were upset by the Red Sox-then totaled 15 home runs over 173 games for the Nationals and Padres over the next two years to finish his career.
Ryan made his MLB debut in Minnesota about six weeks after the trade and hasn’t exited the Twins’ rotation since. Over six seasons he’s made two All-Star teams while recording a 3.73 ERA in 136 games, racking up 850 strikeouts and 13.3 bWAR in 755 2/3 innings. By acquiring a player who’d become one of the league’s most consistent starting pitchers, the Twins absolutely maximized the potential of trading away a 41-year-old.
6. Cubs give up Dylan Cease, Eloy Jimenez for Jose Quintana (2017)
Cubs receive: Jose Quintana
White Sox receive: Eloy Jimenez, Dylan Cease, Matt Rose and Bryant Flete
One year after breaking their historic 108-year World Series drought, the Cubs wanted more. Theo Epstein swung big at the 2017 deadline, trading two of their top four prospects in Dylan Cease and Eloy Jimenez for 28-year-old starter Jose Quintana.
Quintana was O.K. over his three-plus seasons with the Cubs, logging a 4.24 ERA and 8.6 K/9 over 82 appearances (78 starts). But he pitched poorly in the deciding Game 5 of the 2017 NLCS in an 11–1 loss to the Dodgers, which would be his last postseason appearance for Chicago.
Jimenez got off to a hot start in his career with the White Sox but has flamed out. Cease, though, has fared the best of any players involved in this trade. He finished runner-up to Justin Verlander in the 2022 AL Cy Young race and has led the league in strikeouts per nine innings twice since ’21. Cease recorded 16.6 bWAR for the White Sox and Padres before reaching free agency, where he signed with the Blue Jays and found immediate success, earning the starting nod in the 2026 All-Star Game for the AL squad. He enters August with a 2.46 ERA and league-best 13.3 K/9 for the Blue Jays.
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That would’ve looked quite nice in a Cubs uniform.
5. Dodgers trade Yordan Álvarez for a reliever (2016)
Dodgers receive: Josh Fields
Astros receive: Yordan Álvarez
This is an example of how the pursuit of a championship can wind up being incredibly short-sighted. The Dodgers desperately needed relief help in 2016, so they sent a recently signed international prospect to the Astros for righty Josh Fields. It did not work out for L.A.
That wasn’t Fields’s fault-he spent two-plus seasons with the Dodgers and was very good in his role. The former first-round pick went 8–2 with a 2.61 ERA and a 1.04 WHIP in 124 appearances. He was not included on the team’s postseason roster in 2018, was DFA’d in March ’19 and never again pitched in the majors.
In exchange for a middle reliever, the Dodgers sent the Astros a future All-Star and MVP candidate. Since his debut in 2019, Álvarez has been one of the best hitters in baseball. He’s a four-time All-Star, won a Silver Slugger and helped the Astros to a World Series title in 2022. His career slash line is .300/.395/.582 and his lifetime wRC+ of 167 is phenomenal. This season he’s a strong favorite to win the AL MVP award, as he’s hitting an AL-best .325 while leading the majors in home runs (35), OPS (1.082) and OPS+ (201).
This is a big-time regret for the Dodgers.
4. Pirates send Rays a haul for Chris Archer (2018)
Pirates receive: Chris Archer
Rays receive: Tyler Glasnow, Austin Meadows and Shane Baz
As mentioned above, teams know by now to be careful when trading with the Rays. This deal is one of the biggest reasons why they’ve earned that reputation.
Entering the deadline on a 15–4 hot streak, the Pirates opted to buy and landed that year’s most prized trade acquisition in Archer, a two-time All-Star who was under contract through the 2021 season.
Archer’s career tanked as soon as he landed in Pittsburgh. He ended up making just 33 subpar starts for the Pirates, logging a 4.92 ERA and serving up nearly two homers per nine innings pitched. The Pirates declined his club option ahead of the ’20 campaign.
It was a disaster of a trade. Down in Tampa, Glasnow became one of the game’s most dominant pitchers (when healthy). Meadows was an All-Star in 2019, batting .291/.364/.558 with 33 homers and helped the team make three straight playoff appearances, including the 2020 World Series. Shane Baz didn’t debut until 2021, partially due to the lost minor-league season of ’20, and battled rotten injury luck thereafter, but he did record a 4.25 ERA over 54 starts in Tampa Bay and is now a solid rotation member in Baltimore.
3. Padres trade the farm for Juan Soto (2022)
Padres receive: Juan Soto and Josh Bell
Nationals receive: James Wood, C.J. Abrams, MacKenzie Gore, Luke Voit, Robert Hassell III and Jarlin Susana
Not surprisingly, A.J. Preller and the Padres went all in at the 2022 deadline, but one big move overshadowed everything else they did. The Padres were widely praised for landing a superstar with two additional years of team control, but it soon became obvious that they surrendered far too much to land a superstar.
The Padres reached the NLCS in 2022 but were bounced by the Phillies in five games. Soto wasn’t great that year, but was excellent in ’23, earning a Silver Slugger while slashing .275/.410/.519 with 35 home runs, a 152 wRC+ and 5.6 WAR. Unfortunately, San Diego missed the playoffs, and decided to trade Soto to the Yankees before the 2024 campaign to avoid losing him for a pittance in free agency. They essentially wound up with pitchers Michael King and Randy Vasquez and catcher Kyle Higashioka, then used one piece from that deal to help land Dylan Cease, who had a good ’24 campaign before imploding in ’25 and leaving in free agency. Higashioka had one solid season before hitting free agency, and Jhonny Brito hasn’t done much since being acquired.
Josh Bell was almost a footnote in this trade, and he played like one after landing in San Diego. He slashed .192/.316/.271 over 26 games with the Padres and produced -0.4 WAR.
Meanwhile, Gore became an All-Star in Washington before being traded to the Rangers this offseason, while Wood and Abrams have developed into two of the best hitters in the National League. Hassell’s development stalled in Triple A, but Susana has become a top 100 prospect with a triple-digit fastball and an elite slider.
The Padres swung big on this trade and missed, unless the goal was just to get to the NLCS with Soto. The Nationals came out looking brilliant.
2. White Sox surrender Tatis Jr. for James Shields (2016)
White Sox receive: James Shields
Padres receive: Fernando Tatis Jr. and Erik Johnson
This trade technically wasn’t a deadline deal-it went through on June 4, 2016-but it was during the summer months and bad enough to land on this list.
In 2016, the White Sox were in the midst of a six-year run of never finishing higher than fourth place in the AL Central. They landed Shields in an attempt to halt that streak-plus, the Padres planned to pay half of the $58 million remaining on his contract.
Unfortunately for the South Siders, they gave up too much. The White Sox sent a 17-year-old Fernando Tatis Jr. to San Diego as part of the deal, who had yet to make his professional debut after signing with Chicago as an international free agent. By 2018, Tatis was a top-10 prospect in all of baseball. He debuted the following year and is now the face of the Padres as a three-time All-Star, two-time Platinum Glove winner and two-time Silver Slugger honoree. Shields was below replacement level in three seasons in Chicago, and never caught onto another major-league roster.
The Padres are a popular team on this list for all the wrong reasons, but they got this one right.
1. Mets ship Pete Crow-Armstrong to Cubs for Javy Báez (2021)
Mets receive: Javier Báez and Trevor Williams
Cubs receive: Pete Crow-Armstrong
The Mets want this one back.
At the time of this deadline deal, New York was in first place in the NL East, chasing its first division title since 2015. The Cubs were five games below .500 and in the process of moving on from their ’16 championship core. One of those pieces was Javier Báez.
Báez actually had a productive stint with the Mets, batting .299/.371/.515 with nine homers in 47 games, but the team around him collapsed. New York went 21–37 over the final two months of the season and missed the playoffs entirely with a 77–85 record. Báez departed in free agency that winter and signed a six-year deal with the Tigers. Williams stuck around with the Mets for 2022 and finished his New York tenure with a solid 3.17 ERA and 1.28 WHIP over 40 games (12 starts).
Meanwhile, Crow-Armstrong has morphed into one of baseball’s biggest stars. When the Mets selected him with the No. 19 pick of the 2020 draft, Crow-Armstrong was regarded as an elite center fielder with unrealized potential at the dish. He’s now fulfilling his talent as an All-Star center fielder with incredible speed on the base paths and a bat that hit 31 homers last season. Crow-Armstrong has developed better plate discipline this year and as a result is one of the NL MVP front-runners with a .285/.384/.535 slash line, 23 homers and 26 stolen bases in 107 games.
A decade of Crow-Armstrong for 47 games of Javy Baez and a swingman? Oof. That one stings.
More MLB from Sports Illustrated
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- Five Realistic Tarik Skubal Trade Packages We Made With a Value Simulator
- The Stance Change That Saved Manny Machado’s Season
- Four Realistic Mason Miller Trade Proposals Using a Trade Value Model
- MLB Veteran Alek Thomas Run Over By Minor-League Mascot Riding on Scooter
This article was originally published on www.si.com as Ranking the 10 Biggest MLB Trade Deadline Mistakes of the Last Decade.
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This story was originally published July 30, 2026 at 4:00 AM.