Ranking 20 MLB Trade Deadline Deals That Continue to Haunt Teams
Trade deadline deals are all about instant gratification for contending MLB teams looking to shore up their roster for a World Series run.
However, they can often have long-term ramifications, since it's generally young prospect talent heading the other way trades for established veteran talent.
The true winners and losers of deadline trades are not always clear until several years down the line when those prospects have had an opportunity to develop and emerge as big league contributors in their own right.
Ahead we've highlighted 20 trade deadline deals that have come to haunt teams, and it's largely a collection of players who were traded as prospects and have since developed into impact players whose value far exceeds what the contending team acquired at the time of the trade.
The focus here was on active players who are still playing for the team that originally acquired them at the deadline, and even with those specific parameters, there was still a long list of potential candidates.
Nos. 20-19
1 of 15
20. Bailey Falter to the Pirates (Aug. 1, 2023)
To PIT: LHP Bailey Falter
To PHI: IF Rodolfo Castro
Falter has developed into a reliable back-of-the-rotation starter since joining the Pirates, posting a 4.38 ERA in 242.1 innings over 46 starts, and he is under club control through the 2028 season.
Meanwhile, Castro played just 14 games for the Phillies and went 3-for-30 with 12 strikeouts and minus-0.4 WAR.
19. Daniel Palencia to the Cubs (July 26, 2021)
To CHC: RHP Daniel Palencia, OF Greg Deichmann
To OAK: LHP Andrew Chafin
Armed with a triple-digits fastball, Palencia has emerged as the closer for a contending Cubs team. After posting a 5.02 ERA in 37 appearances the last two years, he has turned a major corner with a 1.83 ERA, 0.81 WHIP and 9.6 K/9 in 18 games while tallying four saves and five holds.
Chafin was a two-month rental for an A's team that won 86 games and missed the postseason.
Nos. 18-17
2 of 15
18. Pete Fairbanks to the Rangers (July 13, 2019)
To TEX: RHP Pete Fairbanks
To TB: IF Nick Solak
The Rangers looked like early winners in this deal when Solak hit .293/.393/.491 for a 123 OPS+ over 135 plate appearances after making his MLB debut a month after he was acquired.
Instead, that proved to be his peak, while Fairbanks has a 2.93 ERA, 1.19 WHIP and 11.5 K/9 with 73 saves in 229 appearances over seven seasons in Tampa Bay. With a $7 million club option for next year, he could be one of the top bullpen arms on the move this summer.
17. Ryan Weathers to the Marlins (Aug. 1, 2023)
To MIA: LHP Ryan Weathers
To SD: 1B Garrett Cooper, RHP Sean Reynolds
Things never quite clicked for Weathers in San Diego after he was taken No. 7 overall in the 2018 draft. He logged a 5.73 ERA in 143 innings before he was flipped to the Marlins for a rental bat (Garrett Cooper) and a middle reliever (Sean Reynolds).
Weathers took a major step forward last year with a 3.63 ERA and 1.18 WHIP in 86.2 innings last year, and with club control through 2028, he now looks like one of the few viable building blocks on the Marlins roster.
Nos. 16-15
3 of 15
16. Kyle Manzardo to the Guardians (July 31, 2023)
To CLE: 1B Kyle Manzardo
To MIL: RHP Aaron Civale
Manzardo has a 109 OPS+ with 10 home runs in 49 games this season hitting in the middle of the Guardians lineup, and with club control through 2030, he represents a low-cost run producer for an organization on a budget.
Civale logged a 5.17 ERA over 27 starts with the Rays in 2023 and 2024 before he was traded again last summer, with the Brewers acquiring him in exchange for low-level shortstop Gregory Barrios.
15. Reese Olson to the Tigers (July 30, 2021)
To DET: RHP Reese Olson
To MIL: LHP Daniel Norris
Olson made his MLB debut roughly two years after this trade, and he has since developed into a staple in the Detroit rotation with a 3.60 ERA, 1.16 WHIP and 255 strikeouts in 264.2 innings. The 25-year-old is controllable through the 2029 season and is off to a fantastic start this year with a 2.96 ERA and 2.93 FIP in 48.2 innings.
Norris had a 6.64 ERA in 18 appearances with the Brewers after the trade before departing in free agency during the offseason. He played the prospect role in another trade deadline blockbuster early in his career, going from the Blue Jays to the Tigers in exchange for David Price in 2015.
Nos. 14-13
4 of 15
14. Yennier Cano, Cade Povich to the Orioles (Aug. 2, 2022)
To BAL: RHP Yennier Cano, LHP Cade Povich, LHP Juan Rojas, RHP Juan Nunez
To MIN: RHP Jorge López, cash
This trade raised more than a few eyebrows at the time as a contending Orioles team traded away its All-Star closer, but it ended up being a win in the years that followed.
Cano was an All-Star in 2023, and he has pitched to a 3.24 ERA with 13 saves and 74 holds in 167 appearances with the Orioles. Povich is still trying to find his footing in the big leagues, but he is one of the organization's best young arms, and his 5.29 ERA this year is backed by a 4.47 FIP with 53 strikeouts in 51 innings.
13. Jhoan Durán to the Twins (July 27, 2018)
To MIN: RHP Jhoan Durán, OF Gabriel Maciel, OF Ernie De La Trinidad
To ARI: IF Eduardo Escobar
Escobar had a 35-homer, 118-RBI season for the D-backs in 2019 and he was an All-Star in 2021, so this one was not a complete loss for Arizona, but it's still one they would like to have back given the opportunity.
Maciel was actually the biggest prospect piece at the time of the trade, while Durán was a 20-year-old pitching at the Single-A level. He has since developed into one of the most overpowering bullpen arms in the sport with a 2.40 ERA, 1.09 WHIP and 11.5 K/9, tallying 67 saves in 200 appearances.
Nos. 12-11
5 of 15
12. Wilyer Abreu to the Red Sox (Aug. 1, 2022)
To BOS: OF Wilyer Abreu, IF Enmanuel Valdez
To HOU: C Christian Vázquez
Abreu was not even a top 30 prospect in the Astros system when he was sent to the Red Sox as part of the deal to acquire Vázquez, who was a two-month rental that logged minus-0.1 WAR in 35 games.
He broke out at the Double-A level in 2022 and made his MLB debut in 2023 before earning a starting role in the Red Sox outfield last year, posting a 116 OPS+ with 33 doubles, 15 home runs, 58 RBI and 3.4 WAR while taking home AL Gold Glove honors. The 25-year-old has a 133 OPS+ and 13 home runs in 55 games to open the 2025 campaign.
11. Kyle Stowers, Connor Norby to the Marlins (July 30, 2024)
To MIA: OF Kyle Stowers, IF Connor Norby
To BAL: LHP Trevor Rogers
The Marlins roster is thin on long-term building blocks, but Stowers and Norby both look like keepers, and Stowers has been one of the biggest breakout hitters of the 2025 season with a 135 OPS+ and 10 home runs in 214 plate appearances to open the year.
Flipping some of their young bats for pitching made a ton of sense for the Orioles, but Rogers has been a major bust. The 2021 NL Rookie of the Year runner-up had a 7.11 ERA in 19 innings over four starts after he was acquired last year, and he is currently struggling in the minors.
10. Luis Castillo to the Mariners
6 of 15
Date: July 30, 2022
To SEA: RHP Luis Castillo
To CIN: IF Noelvi Marte, SS Edwin Arroyo, RHP Levi Stoudt, LHP Andrew Moore
If the Cincinnati Reds did not intend to sign Luis Castillo to a long-term deal, they sold on him at the right time, sending him to the Seattle Mariners with one full year of club control remaining.
The deal also brought back a pair of Top 100-caliber prospects in Noelvi Marte and Edwin Arroyo, but a lack of production from Marte has left it difficult to wonder if the Reds could have gotten more for their young ace.
The Mariners moved quickly to sign Castillo to a five-year, $108 million extension a few months after acquiring him, and that now looks like a steal in a market where back-end starters are getting $15 million annually.
Marte is showing some signs of life after a 2024 season lost to a PED suspension and Arroyo is still only 21 years old and widely regarded as one of the best defensive shortstops in the minors, but for now this one still looks like a miss by the Cincinnati front office.
9. Yainer Diaz to the Astros
7 of 15
Date: July 30, 2021
To HOU: C Yainer Diaz, RHP Phil Maton
To CLE: OF Myles Straw
This looked like a swap of speedy center fielder Myles Straw for workhorse reliever Phil Maton at the time of the trade, but the X-factor was a young catcher hitting .314/.357/.464 with 25 extra-base hits in 61 games at Single-A.
Yainer Diaz quickly developed into a top prospect after joining the Houston organization, hitting .306/.356/.542 with 22 doubles, 25 home runs and 96 RBI in 105 games between Double-A and Triple-A in his first full year with the club.
He posted back-to-back 3-WAR seasons to begin his run in the big leagues, including a 2024 campaign where he hit .299/.325/.441 with 29 doubles, 16 home runs and 84 RBI while taking over as the team's primary catcher.
The Guardians gave Straw a five-year, $25 million extension prior to the 2022 season and he responded with a 2.7-WAR campaign and AL Gold Glove honors, but his production dropped off significantly from there and he was sent to Toronto this past offseason in a salary dump.
8. Josh Smith to the Rangers
8 of 15
Date: July 29, 2021
To TEX: IF Josh Smith, IF Ezequiel Durán, RHP Glenn Otto, OF Trevor Hauver
To NYY: OF Joey Gallo, LHP Joely Rodríguez, cash
Slugger Joey Gallo had a 138 OPS+ and 4.1 WAR in 95 games when the New York Yankees acquired him at the 2021 trade deadline for a package of prospects headlined at the time by Ezequiel Duran.
Gallo went on to hit .159 with an 84 OPS+ and a 38.7 percent strikeout rate in 140 games in pinstripes, and while Durán has developed into a useful utility player, it's Josh Smith who has turned out to be the prize of the return package.
A utility player himself, Smith stepped into a large role last season when third baseman Josh Jung missed significant time, posting a 111 OPS+ with 30 doubles, 13 home runs, 62 RBI, 11 steals and 3.2 WAR in 149 games.
To throw salt in the wounds, the Yankees now have a glaring hole at third base, and Smith would be the perfect player to fill it.
7. Cole Ragans to the Royals
9 of 15
Date: June 30, 2023
To KC: LHP Cole Ragans, OF Roni Cabrera
To TEX: LHP Aroldis Chapman
At surface level, getting an ace-caliber starter with club control through the 2028 season in exchange for a two-month rental of Aroldis Chapman might seem like it deserves to rank higher on this list.
However, similar to the 2016 deal that sent Gleyber Torres to the Yankees for a Chapman rental, the deal ultimately helped deliver a World Series title. Chapman was one of the few reliable relievers in the Texas bullpen during their 2023 playoff run, and they might not hoist the trophy without his contributions.
That said, it's still tough to swallow watching Ragans almost immediately emerge as a frontline starter following the trade.
After scuffling to a 5.92 ERA in 17 appearances out of the Texas bullpen prior to the deal, he posted a 2.64 ERA, 1.07 WHIP and 89 strikeouts in 71.2 innings over 12 starts following the trade. He then backed that performance up by finishing fourth in AL Cy Young voting last year, giving the Royals a young, controllable ace.
6. Joe Ryan to the Twins
10 of 15
Date: July 22, 2021
To MIN: RHP Joe Ryan, RHP Drew Strotman
To TB: DH Nelson Cruz, RHP Calvin Faucher
Time and time again, the Tampa Bay Rays have come out on top in under-the-radar trades that end up looking like absolute steals once the dust settles, but this is one where they were on the wrong end of things.
Looking to shore up the lineup for a playoff push, they swung a deal to acquire 40-year-old slugger Nelson Cruz, who had a 148 OPS+ with 19 home runs and 50 RBI in 85 games at the time of the trade.
He went on to post a 101 OPS+ with 13 home runs and 36 RBI the rest of the way, helping the Rays to a 100-win season and the AL East title, but they were ousted by the Boston Red Sox in the ALDS.
Pitching prospect Joe Ryan went the other way in the trade, and while he was pitching for Team USA in the Olympics at the time of the deal, he eventually joined the MLB rotation and logged a 4.05 ERA with 30 strikeouts in 26.2 innings down the stretch.
He has since developed into a staple in the Minnesota rotation, posting a 3.76 ERA in 533.1 innings, and he is making a strong case for his first All-Star selection this year with a 2.57 ERA, 0.83 WHIP and 72 strikeouts in 63 innings.
5. Andres Munoz to the Mariners
11 of 15
Date: Aug. 31, 2020
To SEA: RHP Andrés Muñoz, 1B Ty France, C Luis Torrens, OF Taylor Trammell
To SD: C Austin Nola, RHP Austin Adams, RHP Dan Altavilla
Andrés Muñoz is the best closer in baseball right now.
The 26-year-old has yet to allow an earned run over his first 23.2 innings of work this season, nailing down 17 saves while allowing just eight hits and a .104 opponents' batting average.
The motivating factor in this deal for the Padres was catcher Austin Nola, who was hitting .306/.373/.531 for a 151 OPS+ in 110 plate appearances at the time of the trade, shoring up a major need on the San Diego roster.
His production declined almost immediately after the trade and he profiled more as a defensive-minded backup the rest of his time in San Diego, while the Mariners ended up walking away with a controllable bullpen ace and an All-Star first baseman in Ty France.
It was an aggressive move by the Padres during a shortened 2020 campaign where they thought a World Series run was a real possibility, it simply didn't work out in their favor.
4. James Wood, MacKenzie Gore, CJ Abrams to Padres
12 of 15
Date: Aug. 2, 2022
To WAS: OF James Wood, LHP MacKenzie Gore, SS CJ Abrams, RHP Jarlin Susana, OF Robert Hassell III, 1B Luke Voit
To SD: OF Juan Soto, 1B Josh Bell
It's difficult to decide where to place this trade in the rankings, as it is simply in a category of its own in terms of scale.
Slugger James Wood is one of baseball's most promising young stars, CJ Abrams is an All-Star shortstop and MacKenzie Gore has developed into the ace of the Nationals staff. Throw in a flame-throwing prospect in Jarlin Susana and a potential starting outfielder in Robert Hassell III and this trade has completely reshaped the Nationals organization.
On the other hand, while Juan Soto failed to deliver a World Series title during his time in San Diego, he was eventually flipped for right-hander Michael King and a package of other players.
Would the Padres like to have all those young pieces back?
Absolutely, but the deal was not a complete bust, and they managed to salvage Soto's value by flipping him before he walked in free agency.
3. Oneil Cruz to the Pirates
13 of 15
Date: July 31, 2017
To PIT: OF Oneil Cruz, RHP Angel German
To LAD: LHP Tony Watson
Tony Watson was one of the best setup relievers in baseball during his time with the Pittsburgh Pirates, and he filled a clear need on the Los Angeles Dodgers roster as a second reliable lefty out of the bullpen for a team that won 104 games and reached Game 7 of the World Series.
Acquiring him in exchange for an 18-year-old lottery ticket playing in Single-A and hitting .240/.293/.342 with 110 strikeouts in 89 games at the time of the trade made perfect sense for a team in win-now mode.
Unfortunately for the Dodgers, that teenager was Oneil Cruz, and he has since developed into one of the game's most exciting power-speed threats.
He will never be the most disciplined hitter and he is still figuring things out in center field, but Cruz has a 132 OPS+ with 12 home runs and 18 steals in 49 games to start the 2025 season.
That comes on the heels of a 21-homer, 22-steal, 2.5-WAR campaign last year, and for a Pirates team lacking in impact bats, he is the most dynamic offensive player on the roster.
2. Pete Crow-Armstrong to the Cubs
14 of 15
Date: July 30, 2021
To CHC: OF Pete Crow-Armstrong
To NYM: SS Javier Báez
Javier Báez spent 47 games with the New York Mets, hitting .299/.371/.515 with nine home runs, 22 RBI and 1.7 WAR for a team that ultimately finished 77-85 and missed the postseason by 13 games.
That's what the Mets received in exchange for a player who is rapidly becoming one of the brightest young stars in baseball.
Pete Crow-Armstrong was the No. 19 overall pick in the 2020 draft, so it's as if his recent success has come out of nowhere, and he was the No. 4 prospect in the Mets organization at the time of the trade. That alone is a questionable amount of value to give up for a two-month rental when your team is a fringe contender at best.
Always viewed as an elite outfielder with top-of-the-scale speed, there were some legitimate questions whether Crow-Armstrong would hit enough to be an impact player, but he was also still only 19 years old and far from a finished product at the time of the trade.
After flashing some exciting tools as a rookie last year, he has broken through as a bona fide star, leading the NL with 3.3 WAR through 56 games while hitting .275/.303/.563 for a 143 OPS+ with 13 doubles, 15 home runs, 50 RBI and 16 steals. Throw in his Gold Glove defense and he is a legitimate franchise player.
The lesson here: Don't mortgage quality prospect talent for a two-month rental when you're hovering around .500 at the trade deadline.
1. Yordan Alvarez to the Astros
15 of 15
Date: Aug. 1, 2016
To HOU: DH Yordan Alvarez
To LAD: RHP Josh Fields
With a more well-rounded game, it might not be long before Pete Crow-Armstrong stakes claim to the No. 1 spot in these rankings, but for now Yordan Alvarez is still the top dog when it comes to deadline trade chips teams would love to have back.
The Los Angeles Dodgers traded Alvarez roughly six weeks after signing him for $2 million out of Cuba, and before he ever made his pro debut in the Dodgers organization.
In return, they got a serviceable middle reliever in Josh Fields who logged a 2.61 ERA in 124 appearances over parts of three seasons with the team.
By the beginning of the 2018 season, Alvarez had established himself as a leaguewide Top 100 prospect, and in 2019 he ran away with AL Rookie of the Year honors when he hit .313/.412/.655 with 27 home runs and 78 RBI in 87 games.
Over the past four seasons, he has hit .296/.387/.571 for a 165 OPS+ while averaging 31 doubles, 34 home runs, 96 RBI and 5.0 WAR as one of the best offensive players in baseball.
He probably has to play left field since Shohei Ohtani is locked in at designated hitter, but just imagine adding him to that Dodgers lineup.
