The Worst All-Time MLB Trade Deadline Move for Every Team
The beauty of most deals made at the MLB trade deadline is that the full picture won't be clear until years later, as prospect development is often the determining factor in who "wins" the trade.
If a team gives up a teenager who develops into a superstar for a two-month rental that doesn't even net them a playoff berth, it might have made sense at the time, but ends up looking disastrous in hindsight.
We're going to fully embrace the benefit of hindsight here.
Ahead we've highlighted the worst trade deadline move of all-time for each of the 30 MLB franchises, going back as far as 1986 when the trade deadline was first moved from June 15 to July 31.
Apologies in advance to every fanbase for reopening old wounds, just remember every team has one.
Arizona Diamondbacks
1 of 30
Date: July 8, 1999
To ARI: RP Matt Mantei
To FLA: SP Brad Penny, RP Vladimir Nรบรฑez, OF Abraham Nรบรฑez
With 22 saves and 15.2 K/9 in 30 appearances after he was acquired, Matt Mantei immediately solved the D-backs need for a closer, but he served up a walk-off, series-clinching home run to Todd Pratt in the 1999 NLDS.
Elbow issues derailed his rise as a dominant late-inning arm in the years that followed, and he was eventually supplanted by Byung-Hyun Kim.
Meanwhile, Brad Penny joined the Marlins rotation in 2000, and was a key member of their 2003 World Series team. He went on to play 14 MLB seasons, logging a 4.29 ERA and 1,273 strikeouts in 1,925 innings while earning a pair of All-Star selections.
Athletics
2 of 30
Date: July 31, 2014
To ATH: SP Jon Lester, OF Jonny Gomes, cash
To BOS: OF Yoenis Cรฉspedes, 2015 competitive balance pick
At 66-41, the Athletics had the best record in baseball at the 2014 trade deadline, and they had already swung one blockbuster deal to acquire Jeff Samardzija from the Cubs.
Still looking to add, general manager Billy Beane pulled off a stunning move when he acquired proven playoff ace Jon Lester from the Red Sox, sending starting left fielder and middle-of-the-order slugger Yoenis Cespedes the other way.
It ended up being a major blow to team chemistry, and the Athletics stumbled to a 22-33 record the rest of the way before getting bumped by the Royals in the AL Wild Card Game.
Atlanta Braves
3 of 30
Date: July 31, 2007
To ATL: 1B Mark Teixeira, RP Ron Mahay
To TEX: SS Elvis Andrus, C Jarrod Saltalamacchia, RP Neftalรญ Feliz, SP Matt Harrison, RP Beau Jones
It's hard to properly articulate just what a staggering package of talent this was for the Braves to give up, especially for a franchise that had built a perennial contender largely on homegrown talent.
Jarrod Saltalamacchia (No. 18) and Elvis Andrus (No. 65) were both on the Baseball America Top 100 prospect list, while Beau Jones (No. 9) and Matt Harrison (No. 10) also ranked among Atlanta's top 10 prospects.
The Braves finished 84-78 and missed the playoffs, and the following year they cut their losses on Teixeira and flipped him to the Angels. The Rangers ended up with multiple core pieces for what would be back-to-back AL pennant winners in 2010 and 2011.
Baltimore Orioles
4 of 30
Date: July 2, 2013
To CHC: SP Jake Arrieta, RP Pedro Strop
To BAL: SP Scott Feldman, C Steve Clevenger
A Top 100 prospect prior to the 2009 and 2010 seasons, Jake Arrieta never quite found his groove in Baltimore, posting a 5.46 ERA in 358 innings across parts of four seasons in the rotation.
The rebuilding Cubs bought low on his potential with an early deadline move in 2013, sending veteran rental starter Scott Feldman the other way for an O's team chasing a playoff spot they would fall short of claiming.
By 2015, Arrieta was the NL Cy Young winner, and the following year he helped deliver a long-awaited World Series title on the North Side. Pedro Strop also developed into a terrific late-inning arm, logging a 2.88 ERA and 10.3 K/9 in 413 appearances with the Cubs.
Boston Red Sox
5 of 30
Date: Aug. 30, 1990
To BOS: RP Larry Andersen
To HOU: 1B Jeff Bagwell
This stands as one of the most lopsided trades in MLB history, despite the fact that Larry Andersen did exactly what the Red Sox hoped he would do down the stretch with a 1.23 ERA and a 25-to-3 strikeout-to-walk ratio over 22 innings out of the bullpen.
The veteran reliever walked in free agency ahead of the 1991 season, while Jeff Bagwell ascended as the Astros starting first baseman and promptly won NL Rookie of the Year honors.
He added an MVP award, four All-Star selections, 449 home runs, 1,529 RBI, 79.9 WAR and a Hall of Fame bust in Cooperstown over 15 seasons in Houston.
Chicago Cubs
6 of 30
Date: July 13, 2017
To CHC: SP Jose Quintana
To CWS: SP Dylan Cease, OF Eloy Jimenez, 1B Matt Rose, IF Bryant Flete
Trying to avoid a World Series hangover, the Cubs pulled the trigger on a blockbuster deal with their crosstown rivals, paying a steep price to acquire controllable lefty Jose Quintana.
Slugger Eloy Jimรฉnez was the headliner at the time, and he debuted with a 31-homer season in 2019, but his development stalled due to injuries and one-dimensional contributions.
However, right-hander Dylan Cease has developed into a bona fide ace, and could have been the best homegrown Cubs starting pitcher in years if he stuck around. Quintana had a 4.24 ERA and 102 ERA+ in 439.2 innings on the North Side.
Chicago White Sox
7 of 30
Date: July 31, 1997
To CWS: RP Keith Foulke, RP Bob Howry, SS Mike Caruso, RP Lorenzo Barcelรณ, RP Ken Vining, OF Brian Manning
To SF: SP Wilson รlvarez, RP Roberto Hernรกndez, SP Danny Darwin
The White Sox were 3.5 games back in the AL Central standings when they traded away their ace, their All-Star closer and another piece from their starting rotation in what would be deemed the "White Flag trade" by the media.
"Anyone who thinks we can catch Cleveland is crazy," White Sox chairman Jerry Reinsdorf told Toni Ginnetti of the Sun-Times in an attempt to justify the decision.
Keith Foulke developed into an All-Star closer and Mike Caruso spent a few seasons as the White Sox starting shortstop, but the return here was almost irrelevant to the bigger story of a front office giving up on a contender.
Cincinnati Reds
8 of 30
Date: July 30, 2022
To CIN: OF Noelvi Marte, SS Edwin Arroyo, RP Levi Stoudt, RP Andrew Moore
To SEA: SP Luis Castillo
Noelvi Marte (No. 18 on BA Top 100) was a consensus top-25 prospect in baseball and Edwin Arroyo was on his way to joining the Top 100 list when they were sent to the Reds as the headliners of a package to acquire Luis Castillo.
At the time, it looked like a solid return for a frontline-caliber starter with one additional year of club control remaining, and he has been a rock-solid piece of a terrific rotation since getting to Seattle.
However, with the benefit of hindsight, Marte and Arroyo have contributed a combined negative-1.0 WAR over 282 games in the majors. A more successful job cashing in their best trade chip may have changed Cincinnati's trajectory over the last few seasons.
Cleveland Guardians
9 of 30
Date: July 30, 2011
To CLE: SP Ubaldo Jimรฉnez
To COL: SP Drew Pomeranz, SP Alex White, 1B Matt McBride, SP Joe Gardner
The big story when this trade first broke was Cleveland giving up left-hander Drew Pomeranz, who had just been taken with the No. 5 overall pick in the 2010 draft along with Alex White who was a consensus Top 100 prospect.
Cleveland fell short of making the playoffs in 2011, finishing 80-82, and Jimรฉnez struggled to a 5.40 ERA in 176.2 innings the following year.
He rebounded to go 13-9 with a 3.30 ERA and 194 strikeouts in 182.2 innings in a contract year in 2013, and parlayed that into a four-year, $40 million deal. Pomeranz has put together a solid career, but this is more about Jimรฉnez failing to make the expected level of impact.
Colorado Rockies
10 of 30
Date: July 26, 1993
To COL: SP Greg Harris, SP Bruce Hurst
To SD: SP Andy Ashby, C Brad Ausmus, RP Doug Bochtler
The fledgling Rockies were looking for proven starting pitching during their inaugural season in 1993, and results from veterans Greg Harris and Bruce Hurst in Colorado could not have been much worse.
Harris: 42 G, 32 GS, 4-20, 6.60 ERA, 203.1 IP
Hurst: 3 G, 3 GS, 0-1, 5.19 ERA, 8.2 IP
Andy Ashby immediately turned a corner in San Diego, and went on to log a 3.59 ERA in 1,212 innings while earning two All-Star selections as a member of the Padres. Brad Ausmus developed into one of the best defensive catchers of his era, winning three Gold Glove awards.
Detroit Tigers
11 of 30
Date: Aug. 12, 1987
To DET: SP Doyle Alexander
To ATL: SP John Smoltz
In a bubble, Doyle Alexander is one of the most successful pickups in trade deadline history.
In 11 starts after joining the Tigers, he went 9-0 with a 1.53 ERA in 88.1 innings while tossing three complete game shutouts. Detroit won 98 games and the AL East title, though Alexander was the loser in Game 1 and Game 5 of the ALCS, serving up a combined 14 hits and 10 earned runs in nine innings.
The cost proved incredibly steep, as John Smoltz went on to a Hall of Fame career in Atlanta, debuting in 1988 and breaking through as an All-Star in 1989 before settling in as one of the best pitchers in baseball throughout the 1990s.
Houston Astros
12 of 30
Date: July 12, 2006
To HOU: 3B Aubrey Huff, cash
To TB: 2B Ben Zobrist, SP Mitch Talbot
A middle-of-the-order threat at his peak in Tampa Bay, Aubrey Huff was on the other side of that prime when he joined the Astros. He hit .250/.341/.478 for a 107 OPS+ with 13 home runs and 0.2 WAR in 68 games after the trade, Houston missed the playoffs, and he left in free agency.
In return, the Rays got a versatile Swiss Army knife in Ben Zobrist who ushered in an entire era of super-utility players while racking up 44.7 WAR and winning two World Series titles in 14 seasons.
It's interesting to think how the pieces would have fit if Zobrist would have stuck around and joined Jose Altuve as one of the foundational pieces of Houston's rebuilding efforts.
Kansas City Royals
13 of 30
Date: July 25, 2001
To KC: SS Neifi Pรฉrez
To OAK: OF Jermaine Dye
To COL: 2B Josรฉ Ortiz, OF Mario Encarnaciรณn, RP Todd Belitz
The first trade that might come to mind here is Carlos Beltrรกn going to the Astros in 2004 and putting together an all-time second-half run, but that trade happened in June and the Royals were going to lose Beltrรกn in free agency anyway.
Instead, it's the decision to give up on Jermaine Dye and the middling return of Neifi Pรฉrez that stands above the rest as Kansas City's worst trade deadline decision.
An All-Star in 2000 when he put together a .321/33/118 season, Dye regressed during the first half the following year, and the Royals sold low. He immediately rebounded with a 139 OPS+ in 61 games after the trade and settled in as a consistent run producer, while Pรฉrez logged negative-2.3 WAR in 194 games with the Royals.
Los Angeles Angels
14 of 30
Date: Aug. 7, 2014
To LAA: RP Vinnie Pestano
To CLE: SP Mike Clevinger
The Angels have largely avoided any truly regrettable trade deadline moves, and that stems in part from how infrequently they are buyers, and how rarely they are major sellers.
Vinnie Pestano had a 2.93 ERA and 10.8 K/9 over 192 appearances in Cleveland, and he was lights-out after the trade with a 0.93 ERA in 12 games. The Angels won 98 games, but were swept by the Royals in the ALDS.
He made just 19 more appearances in the majors, while Mike Clevinger became a regular in the Cleveland rotation. He has a 3.55 ERA and 123 ERA+ with 822 strikeouts in 809.2 innings, and netted Cleveland a haul in a 2020 deadline deal with the Padres.
Los Angeles Dodgers
15 of 30
Date: Aug. 1, 2016
To LAD: RP Josh Fields
To HOU: DH Yordan Alvarez
Less than two months after the Dodgers gave him a $2 million signing bonus out of Cuba, the Dodgers flipped Yordan Alvarez to the Astros for middle reliever Josh Fields.
The right-hander posted a 2.61 ERA in 124 appearances during his time in Los Angeles, but worked mostly in low-leverage situations and had a 7.20 ERA over 10 outings in the playoffs.
Alvarez exploded onto the scene to win 2019 AL Rookie of the Year unanimously, and he has been one of the game's elite offensive players ever since. The current AL Triple Crown leader with a .325 average, 35 home runs and 80 RBI in 107 games, he could be headed for MVP honors.
Miami Marlins
16 of 30
Date: July 29, 2016
To MIA: SP Andrew Cashner, RP Tyron Guerrero, cash
To SD: 1B Josh Naylor, SP Jarred Cosart, RP Carter Capps
Originally a seven-player trade that also sent Colin Rea to the Marlins and a young Luis Castillo to the Padres, the deal was revised after Rea left his first Miami start with an elbow strain.
Andrew Cashner struggled to a 5.98 ERA in 52.2 innings after the trade and the Marlins finished 79-83, falling short of the playoff berth they were hunting.
It was not until three years later that Josh Naylor made his MLB debut with the Padres, and the All-Star slugger has been the subject of two other major trade deadline deals, going to Cleveland in 2020 and Arizona in 2025.
Milwaukee Brewers
17 of 30
Date: July 28, 2006
To MIL: OF Kevin Mench, RP Francisco Cordero, OF Laynce Nix
To TEX: OF Carlos Lee, OF Nelson Cruz
Motivated to get something for Carlos Lee before losing him in free agency, the Brewers brought back a controllable outfield replacement in Kevin Mench and a standout closer in Francisco Cordero.
The misstep was including Nelson Cruz as a throw-in secondary piece, and while he was 25 years old with just seven big league plate appearances under his belt at the time of the deal, he went on to be one of the most productive sluggers of his era.
He broke through with a 33-homer season in 2009 and went on to slug 464 home runs while playing through his age-42 campaign in 2023.
Minnesota Twins
18 of 30
Date: July 29, 2010
To MIN: RP Matt Capps
To WAS: C Wilson Ramos, RP Joe Testa
With Joe Nathan injured, the Twins needed help at the back of the bullpen, and they gave up a consensus Top 100 prospect in Wilson Ramos to All-Star Matt Capps from the Nationals.
Joe Mauer's presence in the organization made trading a top-tier catching prospect more understandable, but concussions pushed Mauer to first base a few years later, while Ramos developed into an All-Star.
As for Capps, he pitched well after the trade, but the Twins were swept by the Yankees in the ALDS. The following year he had a 4.25 ERA and nine blown saves in 24 chances before Nathan returned to action.
New York Mets
19 of 30
Date: July 30, 2004
To NYM: SP Victor Zambrano, RP Bartolomรฉ Fortunato
To TB: SP Scott Kazmir, RP Josรฉ Dรญaz
Victor Zambrano had a 4.47 ERA and 100 ERA+ over four seasons in Tampa Bay, so it's not as though he was anything close to a frontline starter at the time of the trade. He did have two additional years of club control, and that was enough for the Mets to part with top-tier pitching prospect Scott Kazmir.
Zambrano made three starts before suffering an elbow injury, turned in a mediocre 2005 season, and then missed almost all of 2006 with a torn flexor tendon. Kazmir was a two-time All-Star in Tampa Bay and quickly developed into one of the best pitchers in franchise history.
The 2000 deadline deal that sent a young Melvin Mora to the Orioles for veteran shortstop Mike Bordick was also a strong contender. Bordick had a 76 OPS+ after the trade and then re-signed with the Orioles, while Mora went on to a 28.3-WAR career.
New York Yankees
20 of 30
Date: July 21, 1988
To NYY: DH Ken Phelps
To SEA: OF Jay Buhner, SP Rick Balabon, SP Troy Evers
"What the hell did you trade Jay Buhner for?! He had 30 home runs and over 100 RBI last year. He's got a rocket for an arm. You don't know what the hell you're doing!"
Those famous words by Frank Costanza to George Steinbrenner on a Seinfeld episode in 1996 forever immortalized this deal as one of the most lopsided trades in deadline history, and it stands up as the Yankees worst deadline move.
Ken Phelps played 131 forgettable games in a Yankees uniform, while Buhner went on to launch 307 home runs in 14 seasons with the Mariners.
Philadelphia Phillies
21 of 30
Date: July 26, 2000
To PHI: SP Vicente Padilla, SP Omar Daal, 1B Travis Lee, SP Nelson Figueroa
To ARI: SP Curt Schilling
The Phillies worst trade deadline move is a toss-up between Curt Schilling to the Diamondbacks or Scott Rolen to the Cardinals, and both moves involved the star player essentially forcing his way out of town.
While the Rolen package at least brought back a solid everyday player in Plรกcido Polanco, the Schilling deal was a major bust, as young slugger Travis Lee failed to develop into the offensive cornerstone he was hyped to be as a prospect.
Curt Schilling won a World Series in 2001 pitching alongside Randy Johnson, and over four seasons with the D-backs he had a 3.14 ERA and 875 strikeouts in 781.2 innings while finishing runner-up to the Big Unit in NL Cy Young voting twice.
Pittsburgh Pirates
22 of 30
Date: July 23, 2003
To PIT: IF Josรฉ Hernรกndez, 2B Bobby Hill, SP Matt Bruback
To CHC: 3B Aramis Ramรญrez, OF Kenny Lofton, cash
Unlikely to be able to afford Aramis Ramรญrez once he reached free agency, the Pirates opted to put a budding offensive star on the trade block when he had two remaining years of control.
He posted a 105 OPS+ with 15 home runs in 63 games after the trade to help the Cubs reach the NLCS, and he went on to tally 239 long balls over nine seasons in Chicago. Kenny Lofton was a pure rental, but plugged a major hole in center field after Corey Patterson was lost for the season, and he alone should have brought back a better return.
Josรฉ Hernรกndez was a 33-year-old journeyman who was released at the end of the season, Bobby Hill tallied 0.1 WAR in 185 games with the Pirates and Matt Bruback never reached the big leagues.
San Diego Padres
23 of 30
Date: July 31, 2010
To SD: OF Ryan Ludwick
To CLE: SP Corey Kluber
To STL: SP Jake Westbrook, RP Nick Greenwood
In a three-team trade that featured two established major leaguers, it was the relatively unknown prospect Corey Kluber who ended up making far and away the biggest impact.
The No. 29 prospect in the San Diego system prior to the 2008 season and unranked heading into 2009, Kluber made his MLB debut the following year before getting knocked around with a 5.14 ERA in 12 starts in 2012.
Then he turned a corner, and during his five-year peak from 2014-18, he went 83-45 with a 2.85 ERA, 1.02 WHIP and 1,228 strikeouts in 1,091.1 innings. He was a three-time All-Star and won AL Cy Young honors in 2014 and 2017, going from late-bloomer to one of the best pitchers of his era.
San Francisco Giants
24 of 30
Date: July 28, 2011
To SF: OF Carlos Beltrรกn, cash
To NYM: SP Zack Wheeler
Carlos Beltrรกn joining the Astros in 2004 was arguably the most productive deadline rental of all-time, so it's easy to see what the Giants envisioned when they traded away top pitching prospect Zack Wheeler for two months of the future Hall of Famer seven years later.
With a .323/.369/.551 line and 20 extra-base hits in 44 games, Beltrรกn did his part, but the Giants finished 86-76 and missed the playoffs by four games.
Wheeler made his MLB debut in 2013 and immediately became a standout in the Mets rotation, eventually pitching his way to a nine-figure free agency deal from the Phillies.
Seattle Mariners
25 of 30
Date: July 31, 1997
To SEA: RP Heathcliff Slocumb
To BOS: C Jason Varitek, SP/RP Derek Lowe
Teams were willing to pay a small fortune for a viable closer in the 1990s, when saves really started to take hold as a go-to measure of late-inning success, and the Mariners got burned chasing a ninth-inning answer in 1997.
Despite a 5.79 ERA in 49 games, Heathcliff Slocumb had 17 saves for the Red Sox, and that was enough for Seattle to give up some legitimate prospect talent to acquire him. He tallied 10 saves down the stretch for the Mariners, then saw his ERA balloon to 5.32 the following year.
Jason Varitek and Derek Lowe piled up a combined 43.6 WAR during their time with the Red Sox, and both were members of the 2004 World Series winning team.
St. Louis Cardinals
26 of 30
Date: July 29, 2000
To STL: RP Jason Christiansen
To PIT: SS Jack Wilson
A tip of the cap to the Cardinals for not having a truly memorable trade deadline deal that blew up in their face, and even this trade is somewhat easily justified by the presence of All-Star shortstop รdgar Renterรญa.
Still, it's never fun to give away a future All-Star, especially to a division rival and in exchange for a middle reliever who was gone a year later.
A former ninth-round pick playing in Double-A at the time, Jack Wilson debuted in 2001 and took over as Pittsburgh's starting shortstop the following year. He quietly logged 21.3 WAR over nine seasons with the Pirates, earning an All-Star selection and Gold Glove in 2004.
Tampa Bay Rays
27 of 30
Date: July 22, 2021
To TB: DH Nelson Cruz, RP Calvin Faucher
To MIN: SP Joe Ryan, SP Drew Strotman
Joe Ryan was pitching for Team USA at the Olympics when he was traded from Tampa Bay to Minnesota at the 2021 deadline, and he made two starts with the Twins' Triple-A affiliate before joining the big league rotation.
He has been a staple of the staff ever since, posting a 3.73 ERA with 850 strikeouts in 755.2 innings, and earning an All-Star nod in 2025 and 2026. A rare mistake by a Tampa Bay organization that has fleeced more than a few clubs out of quality arms.
Nelson Cruz had a 148 OPS+ and 19 home runs at the time of the trade, but saw that shrink to a 101 OPS+ and 13 long balls in 55 games down the stretch. The Rays were bumped in the ALDS, Cruz departed in free agency and Ryan developed into a rotation standout.
Texas Rangers
28 of 30
Date: July 31, 2012
To TEX: SP Ryan Dempster
To CHC: SP Kyle Hendricks, 3B Christian Villanueva
The Cubs initially agreed to send Ryan Dempster to the Braves in exchange for top pitching prospect Randall Delgado, but when that fell apart, they pivoted and sent him to the Rangers for former Top 100 prospect Christian Villanueva and a low-level pitcher.
Years later, that pitcher would start Game 7 of the 2016 World Series and help deliver a championship to the Cubs that was 108 years in the making.
Dempster struggled to a 5.09 ERA in 12 starts after the trade before departing in free agency. Kyle Hendricks made his MLB debut in 2014 for a rebuilding Cubs team, won the NL ERA title two years later for a World Series champion and ended up making 270 starts and tallying 22.2 WAR in 11 seasons on the North Side.
Toronto Blue Jays
29 of 30
Date: July 19, 2000
To TOR: SP Esteban Loaiza
To TEX: IF Michael Young, RP Darwin Cubillรกn
Esteban Loaiza was a 20-game winner and a two-time All-Star with the White Sox, but before that he struggled to establish himself as a rotation regular for multiple teams, including the Rangers.
With a 5.37 ERA in 107.1 innings, he was not the most attractive trade chip at the 2000 deadline, but Texas still managed to flip him to the Blue Jays for a pair of prospects. He was solid for Toronto in the second half, yet he logged an ERA north of 5.00 in each of the next two seasons.
Michael Young made his MLB debut later that year as a September call-up, and took over as the starting second baseman in 2001. Over 13 seasons with the Rangers, he hit .301/.347/.444 with 2,230 hits and 25.9 WAR. He was a seven-time All-Star and won the AL batting title in 2005.
Washington Nationals
30 of 30
Date: July 28, 2015
To WAS: RP Jonathan Papelbon, cash
To PHI: SP Nick Pivetta
Rule No. 1 if you're a newcomer to a playoff contender: Don't try to choke the team's 22-year-old superstar in the dugout.
It sounds like a simple enough rule to follow, but Jonathan Papelbon did just that during an altercation with Bryce Harper on Sept. 28, exactly two months after he was acquired from the Phillies.
Papelbon actually returned the following season for the final year of his contract, but he was released in August with a 4.37 ERA and 1.46 WHIP over 37 games in what was his final MLB action. Nick Pivetta went on to develop into a solid rotation piece for the Phillies, Red Sox and now Padres.
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