TheSportster.com

Top 25 Most One-Sided MLB Trades Involving Active Players

When building a strong baseball roster, a team’s general manager has three primary options: -Trust your scouts and hope the players you’ve drafted progress through the farm system. -Throw a bunc

When building a strong baseball roster, a team’s general manager has three primary options:

-Trust your scouts and hope the players you’ve drafted progress through the farm system.

-Throw a bunch of money at a couple of key free agents each off-season.

-Outsmart your peers in either the short (contending) or long (rebuilding) term via a trade.

Building a team through the draft is surely cost-effective, as the game’s best young players are paid a tiny fraction of what an average veteran earns. But the draft also involves a lot of luck. Of the 40 athletes taken in the first round (including supplemental picks) of the 2000 MLB Amateur Draft, only 23 ever made it to the big leagues, a mere four have a career batting average above .225 and just one won more than 35 MLB games as a pitcher.

Free agency, on the other hand, offers teams a chance to quickly plug holes in their rosters with (relatively) known commodities. However, as more young stars (e.g., Mike Trout and Christian Yelich) sign extensions prior to ever hitting the open market, the quality of players available each off-season has diminished. And of course, the high cost (in both dollars and years) of acquiring a free agent is often prohibitive to a club’s long-term outlook.

Perhaps the single skill that most separates the league’s general managers is the ability to improve their respective teams with a trade. There is no “other side” in free agency. If you offer the most money, you’ll get your man more often than not. Conversely, a trade requires two competing participants to both agree to the same terms. Once the transaction has become official, each party likely feels he’s gotten the better end of the deal (or why would he pull the trigger?). However, just as with most things in sports, there is usually only one side that comes out ahead. Here are 25 trades involving current MLB players in which there was most definitely only one winner.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

25 Josh Donaldson for Franklin Barreto, Kendall Graveman, Brett Lawrie and Sean Nolin

Dan Hamilton-USA TODAY Sports

Donaldson began his professional baseball career as a catcher in the Cubs’ organization, but began transitioning to third base shortly after being acquired by Oakland. The former first round draft pick exploded for a 145 OPS+ (on-base plus slugging percentage relative to the rest of the league, adjusted for ballpark factors, where 100 is average and higher numbers are better) for the A’s in 2013 and was traded to the Blue Jays a year later. During his first season north of the border, Donaldson won the American League MVP Award with 41 home runs, 122 runs and 123 RBI and has been equally impressive this year. He’s one of only two players, along with Angels’ outfielder, Mike Trout, to be among the top six players in all of baseball in WAR during each of his four years as a starter (2013-2016). Lawrie had a typical year for himself (95 OPS+) during his lone season in Oakland and the 25-year old Graveman (10-8, 3.97 ERA this year) seems like he may be a solid mid-rotation pitcher for the A’s.

24 Scott Kazmir and Jose Diaz for Victor Zambrano and Bartolome Fortunato

Eric Hartline-USA TODAY Sports

The 2004 New York Mets finished with a 71-91 record, while the Devil Rays (as they were known back then) were in their seventh year of existence, still looking for their first winning season. Kazmir, a 2002 first-round pick, was 20 years old at the time of the trade and had entered the 2004 season as Baseball America’s 12th-best MLB prospect. Normally, when a team trades a high-level player with that much potential, it’s typically to acquire a veteran who can help the team reach, or advance deep in, the playoffs. When this trade was made, however, the Mets were in last place, 19 games behind the division-leading Atlanta Braves. Zambrano posted a 100 ERA+ (ERA relative to the rest of the league, adjusted for ballpark factors, where 100 is average and higher numbers are better) during his 61 career appearances for Tampa Bay; he was, by that metric, the definition of an average MLB starting pitcher. With the Mets, he had a 10-14 record in 39 games (35 starts), before signing with Toronto as a free agent following the 2006 season. During his time with the Devil Rays, Kazmir went 55-44 with a respectable 114 ERA+ and in 2007, led the league with 239 strikeouts.

23 Ian Kinsler for Prince Fielder

Kirby Lee-USA TODAY Sports

A month ago, this trade would not have made the list. Though Fielder had been plagued by injuries since coming to Texas from Detroit in November 2013, he put together a solid season last year (23 home runs and a 126 OPS+). After 89 games this year, however, Fielder had hit only eight homers to go along with a dismal 65 OPS+. A second neck surgery has led him to promptly retire from the sport mid-season with over $100 million owed to him over the next four-plus years (the Tigers are on the hook for about a quarter of it, but the Rangers must pay the bulk of the remaining money). Fielder wound up hitting a relatively poor 104 OPS+ with Texas over 289 games. Meanwhile, in Detroit, Kinsler keeps plugging along at second base; he’s posted over 16 WAR since the trade. With over a month remaining in the regular season, he has already reached 20 home runs for the first time in five years.

22 Tanner Roark and Ryan Tatusko for Cristian Guzman

Brad Mills-USA TODAY Sports

The 2010 Rangers needed some infield depth as they made a run to the A.L. West division title and, eventually, the World Series. They acquired 32-year old infielder, Cristian Guzman, from Washington, but the one-time Yankee farmhand wound up playing just 15 more games in his career. Guzman hit just .152 with a lone RBI, following the trade to Texas. One of the players the Nationals received in the deal was Tanner Roark, who was never ranked as a top-100 prospect in the big publications. He wasn’t even promoted to the Majors until he was 26 years old. But he has become an important part of the rotation for the N.L. East-leading Nationals this season. In 112 career appearances (74 starts) with Washington, Roark is 39-25 with a solid 127 ERA+. This year, he’s in the top 10 of the National League in both wins (13) and ERA (2.99). Roark will need to continue his strong season, as teammate Stephen Strasburg has recently been placed on the disabled list with an elbow injury.

21 Josh Hamilton for Edinson Volquez and Danny Herrera

Joe Camporeale-USA TODAY Sports

Initially, this trade appeared to be a steal for Cincinnati and then very quickly reversed course. In his first season with the Reds, Volquez, who was just 24 at the time, went 17-6 with a 3.21 ERA, while striking out 9.5 batters per nine innings. In his subsequent three years with the team, he went 13-12 with an ERA just north of 5.00. Hamilton, meanwhile, began hitting from Day 1 in Texas (he singled in his first AB) and rarely let up. He led the league in total bases (331) and RBI (130) during that inaugural season with the Rangers. Two years later, Hamilton won the 2009 A.L. MVP Award, the American League batting title (.359) and had a career-best 170 OPS+. During that five-year stint in Arlington, he clubbed 142 homers and knocked in 506 runs in 647 games. Though he hasn’t played this season because of injury, Hamilton claims he’ll be ready to return in time for spring training in 2017.

20 Carlos Gomez for J.J. Hardy

Tim Heitman-USA TODAY Sports

During his first five seasons with Milwaukee, Hardy twice hit 24 or more home runs. In November 2009, the Twins sent light-hitting (73 OPS+ in two years with the team), 24-year old outfielder, Carlos Gomez, to the Brewers for him and have regretted doing so ever since. Gomez spent five-plus years in Milwaukee and during his two peak seasons, had 47 home runs, 175 runs, 146 RBI, 74 stolen bases and an OPS+ of 129. In 2013, he led the National League with 8.5 WAR (a measure of the number of wins a player adds to his team above what a replacement player would contribute). Hardy, meanwhile, hit .268 with six homers in his one season as a member of the Twins. Minnesota then shipped him to Baltimore a year later for a minor leaguer and reliever, Jim Hoey, who only made 26 appearances (75 OPS+) over the remainder of his career. Of course, Hardy would go on to become a fixture at shortstop for the Orioles for several few years.

19 Adam Eaton for Hector Santiago and Brandon Jacobs

Steve Mitchell-USA TODAY Sports

In 2012, Eaton hit an astounding .381 in 119 games for the Reno Aces (AAA). A year later, the Diamondbacks included him in a three-team deal that netted them slugger Mark Trumbo from the Angels. The White Sox, however, were the real winners in this transaction. In his inaugural season on the South Side of Chicago, Eaton hit .300 with a league-best 10 triples; the following season, he increased his home run total from one to 14. Overall, he has a 118 OPS+ and 14.4 WAR through his first 402 games in the A.L. Still just 27 years old, he should continue to put up good numbers for several more seasons. In return for Eaton, the White Sox sent starting pitcher, Hector Santiago, to the Angels. While in Anaheim, Santiago was an average MLB hurler, posting a 25-22 record and a 99 ERA+. After nearly three seasons with the team, he was flipped for 26-year old Twins’ pitching prospect, Alex Meyer, and veteran, Ricky Nolasco. Since that trade, Nolasco is 0-4 in five starts with a 5.70 ERA for the Angels.

18 Noah Syndergaard, Travis d’Arnaud, John Buck and Wuilmer Becerra for R.A. Dickey, Mike Nickeas and Josh Thole

Lance Iversen-USA TODAY Sports

Though d’Arnaud was once a highly-rated prospect in the Blue Jays’ organization, he hasn’t yet met expectations. For now, this trade simply comes down to Syndergaard and Dickey and it’s not even close. In 2012, Dickey won the National League Cy Young Award by fluttering his knuckleball at hitters to the tune of a 20-6 record and 2.73 ERA. He even led the league in strikeouts (230) and shutouts (3). So Toronto went after him that off-season, despite the fact that Dickey was a.) 38 years old and b.) 41-50 with a 4.34 ERA prior to his big year. Predictably, his stats regressed immediately; in his three-plus seasons with the Jays, he hasn’t finished a season more than a game above .500 and hasn’t had an ERA+ above 104. So Toronto got an average pitcher; what did the Mets receive in the trade? Through his first 49 games (48 starts), Syndergaard is 20-14 with a 2.93 ERA and his K/9IP stands at 10.4. And perhaps best of all for New York, he won’t be eligible for free agency until 2022.

17 Adrian Gonzalez, Terrmel Sledge and Chris Young for Adam Eaton, Akinori Otsuka and Billy Killian

Gary A. Vasquez-USA TODAY Sports

Along with Josh Beckett and Carl Crawford, Gonzalez was part of the second-most famous salary dump in Red Sox history (at least this time, it wasn’t done in order to fund a Broadway show). But it’s another trade involving Gonzalez that makes this list. Prior to the 2006 season, the Rangers sent him and quality starting pitcher, Chris Young to the Padres for three players. Akinori Otsuka stepped into the closer role for Texas, saving 32 games for them in his first year there, but played only one more MLB season. Adam Eaton was an ineffective starter both before (92 ERA+ across six years in San Diego) and after (90 ERA+ during his lone season in Arlington) the trade. Billy Killian, like most of you reading this, never made it to the Majors. While Young (33-25, 110 ERA+ with SD) was a decent pickup for the Padres, Gonzalez really saw his career take off with them. Over five seasons with the team, he posted an impressive 141 OPS+ and averaged over 30 home runs and 100 RBI.

16 Corey Kluber for Jake Westbrook

Jerome Miron-USA TODAY Sports

This three-team trade resulted in a big win for the Cleveland Indians. The main pieces of the deal included Kluber going from San Diego to the Tribe, Westbrook moving from Cleveland to St. Louis and Ryan Ludwick going from the Cardinals to the Padres. Ludwick proceeded to perform horribly after the trade. Though he had smacked 37 home runs two years earlier, he would end his two-year stint in Southern California with just 17 home runs and an OPS+ of just 86 in 160 games. Westbrook, who had been a serviceable starter with the Indians, pitched similarly in St. Louis. The Tribe won this trade easily once Kluber joined their rotation full-time in 2013. He won 11 of his 16 decisions that year and then made a huge leap the following season when he won the American League Cy Young Award with an 18-9 record and a 2.44 ERA. Though he lost 16 games in 2015, he had a FIP (fielding independent pitching, which measures a pitcher’s effectiveness with things he can control) of 2.97, which is in line with his impressive career mark of 2.98.

15 Adam Wainwright, Ray King and Jason Marquis for J.D. Drew and Eli Marrero

Bill Streicher-USA TODAY Sports

With a year remaining on his contract, outfielder J.D. Drew was sent from St. Louis to Atlanta during the 2003 off-season. The Braves needed a right fielder and were willing to trade their top pitching prospect, Adam Wainwright, to get one. To be fair, Drew had a tremendous year while he was in Atlanta. He slugged a career-high 31 home runs, scored 118 runs, had 93 RBI and even stole 12 bases for good measure. Drew finished the season with an OPS of 1.006 and was sixth in the National League MVP voting. All that said, he left as a free agent following the season, while Wainwright went on to become a legitimate ace for the Cardinals. He won 19 or more games four times and was among the top three vote-getters for the N.L. Cy Young Award in each of those seasons. The top of the Braves’ rotation in 2005 consisted of a 38-year old John Smoltz, Horacio Ramirez and Tim Hudson. Drew was a great short-term acquisition, but Atlanta could have really used Wainwright over the subsequent decade.

14 Chris Davis and Tommy Hunter for Koji Uehara

Andy Marlin-USA TODAY Sports

After coming to the United States from Japan as a 34-year old in 2009, Uehara has put together a solid career out of the bullpen. He’s saved 92 games, struck out 10.8 batters per nine innings pitched (K/9IP) and even won a World Series title with the Red Sox in 2013. But he never hit 53 home runs in a season. Chris Davis did just that in 2013, his second full season in Baltimore following the trade from Texas. He scored 103 runs and led the league in homers, RBI and total bases that year. In 740 games with the O’s, Davis has hit the ball out of the park an astounding 191 times (once every 14 at-bats) and owns the game’s two highest single-season home run marks of the past five years. Still just 30 years old, it doesn’t seem likely that he will be slowing down anytime soon, either.

13 Max Scherzer, Austin Jackson, Phil Coke and Daniel Schlereth for Curtis Granderson and Edwin Jackson

Tommy Gilligan-USA TODAY Sports

In four-plus seasons after being traded to Detroit, Jackson accumulated 20.7 WAR, which outpaced Granderson’s 14.4 WAR for the Yankees over nearly the same time frame. Starter, Ian Kennedy, was also involved in this three-team trade, going from New York to Arizona, but netting Scherzer before he blew up qualifies this trade as a big win for the Tigers. While with the Diamondbacks, Scherzer was known as a young, hard-throwing pitcher who hadn’t yet put it all together. Though he was a little inconsistent initially with Detroit, he went 16-7 and led the league with 11.1 K/9IP in 2012. The following season was even more impressive for Scherzer, as he went 21-3 with a 2.90 ERA and a league-leading 0.970 WHIP (walks and hits allowed per inning pitched) en route to the A.L. Cy Young Award. Overall, during his five seasons in The Motor City, he went a ridiculous 82-35 and struck out over a batter per inning.

12 Zack Greinke and Yuniesky Betancourt for Lorenzo Cain, Alcides Escobar and Jake Odorizzi

Steve Mitchell-USA TODAY Sports

In 2009, Greinke won the American League Cy Young Award for Kansas City with a 16-8 record, a 2.16 ERA and a 1.073 WHIP. Milwaukee acquired him after the following season in a trade that helped the Brewers capture their first division title in 29 years. But a year later, in the final year of his contract, they sent him to Anaheim. The Royals managed to use the trade to plug several holes in their roster with players who would eventually become key pieces on their 2015 World Championship team. Last year, Cain made his first All-Star Game, won the ALCS MVP, finished third in the A.L. MVP vote, had a 125 OPS+ and set career highs in virtually every offensive stat. Escobar has not contributed much with his bat during his six years in K.C., but he plays good defense and has stolen 145 bases for the team. Odorizzi’s time with the Royals was brief (two games), but he was used as part of a package that returned starting pitcher, James Shields (27-17, 3.18 ERA before he left as a free agent), and closer, Wade Davis (18-3, 41 saves, 1.09 ERA during the past three seasons out of the bullpen).

11 Jake Arrieta and Pedro Strop for Steve Clevenger and Scott Feldman

Jake Roth-USA TODAY Sports

Before he threw two no-hitters and won a Cy Young Award for the Cubs, Arrieta was a two-time MLB top-100 prospect (by both Baseball America and Baseball Prospectus) for Baltimore. He was never able to realize his potential with the Orioles, however; in 69 appearances (63 starts), he was 20-25 with a horrific 77 ERA+. So the team moved him to the Cubs in a deal that included Scott Feldman, who had once won 17 games with Texas, but was otherwise the very definition of an average MLB pitcher (46-50 with an ERA+ just under 100 at the time of the trade). Feldman only made 15 starts for Baltimore (5-6, 4.27 ERA) before heading to Houston via free agency. Arrieta, meanwhile, has finally met, and exceeded, his lofty expectations. Since the beginning of 2015, he is 38-11 with a microscopic 2.12 ERA. Over 92 starts with the Cubs, Arrieta’s WHIP is just 0.967 and his ERA+ is 164.

10 Mark Teixeira and Ron Mahay for Elvis Andrus, Neftali Feliz, Matt Harrison, Jarrod Saltalamacchia and Beau Jones

Andy Marlin-USA TODAY Sports

This was the trade that helped launch the Texas Rangers into back-to-back World Series appearances. The Braves sent several young players to Arlington in exchange for Teixeira, one of the best sluggers in the game. And while he was with Atlanta, Teixeira produced at an extremely high level. In parts of two seasons, he hit 37 HR and knocked in 134 runs in just 157 games. Rather than lose him for nothing, they then sent Teixeira to Anaheim for Casey Kotchman. But in that initial deal, the Rangers were able to land a starting shortstop, a closer, a mid-rotation pitcher and a backup catcher. Andrus has not hit much (84 OPS+) during his eight-year career, but he plays solid defense, has stolen 235 bases and has 22.4 WAR. Feliz saved 72 games for the two Texas teams that reached the Fall Classic and had a 164 ERA+ over his seven-year tenure with the team. And Harrison has won 50 games for the team, including 32 over 2011-12.

9 Shin-Soo Choo and Shawn Nottingham for Ben Broussard

Isaiah J. Downing-USA TODAY Sports

Prior to this 2006 trade, Choo only had two hits and three walks in 33 career plate appearances with the Mariners. After being acquired in late July, he ended up playing parts of seven seasons in Cleveland. He missed a lot of time early on, but ended up with a 134 OPS+ while playing 685 games for the Tribe. At his peak, Choo hit .300 and had at least 20 homers, 80 runs, 80 RBI and 20 stolen bases in both 2009 and 2010. First baseman, Ben Broussard, didn’t fare as well after he arrived in Seattle. His playing time dropped considerably after the trade and his OPS+ dipped from 112 with the Indians to 91 during his year-and-a-half with the M’s. Following the 2012 season, Cleveland traded Choo and received starting pitcher, Trevor Bauer, among other players. This year, the 25-year old is having his best season to date, with a record of 9-6 to go along with an ERA+ of 121.

8 Brandon Phillips for Jeff Stevens

Charles LeClaire-USA TODAY Sports

Prior to the 2003 season, Phillips was rated by Baseball America as the 7th-best prospect in the game. Three years later, he was dumped by Cleveland after he posted a dismal OPS+ of 48 over 462 plate appearances. Still just 25 at the time, Phillips was immediately installed as the Reds’ starting second baseman and a decade later, he’s in the exact same spot. During his time in Cincinnati, he’s hit 188 homers, stolen 189 bases and has over 800 runs and RBI. Phillips has also made three All-Star Game appearances and won four Gold Gloves as the National League’s best defensive player at his position. He has just over 30 WAR for the Reds and across three postseasons, he’s hit .325 with a pair of home runs in 41 plate appearances. Stevens, the only player Cleveland received in return for Phillips, never played for the team and was eventually traded to the Cubs.

7 Carlos Gonzalez, Huston Street and Greg Smith for Matt Holliday

Isaiah J. Downing-USA TODAY Sports

Following the 2008 MLB season in which they went 75-86, the Oakland A’s went out and traded for the Rockies’ great outfielder, Matt Holliday. During his first five years in the league, Holliday had a 134 OPS+ (keep in mind, that’s adjusted to neutralize the effect of playing in Denver) and famously scored the winning run that sent his team to the 2007 World Series. That year, he was runner-up for the N.L. MVP and led the league in batting average (.340), total bases (386), hits (216), doubles (50) and RBI (137). To get him, Oakland gave up their 24-year old closer, Huston Street, and a highly-touted prospect in Carlos Gonzalez. Holliday only wound up playing 93 games for the A’s with numbers that were good, but well below his standards. The team wasn’t winning, so they flipped him to St. Louis at the trade deadline for three players who would never make a significant impact in the Majors. The Rockies made out very well; Street went on to save 84 games in his three seasons with the team and Gonzalez has blossomed into a legitimate star. In 2010, he won a batting title (.336) and finished third in the N.L. MVP vote. Last year, he belted 40 homers for the first time in his career.

6 Ben Zobrist and Mitch Talbot for Aubrey Huff

Jake Roth-USA TODAY Sports

As the 2006 Houston Astros were making a push for the playoffs (they’d eventually fall a game and a half short of division winner and eventual World Series champion, St. Louis), they acquired Aubrey Huff from the Devil Rays. He had a 107 OPS+ in 68 games with Houston, but the team let him move on in free agency following the season. To get Huff, the ‘stros sent 25-year old Ben Zobrist, an on-base machine with very little power at AA, to Tampa. In 2009, his first full season as a big league starter, Zobrist suddenly discovered his home run swing. He hit 27 balls out of the park that year with an OPS+ of 149 and played all over the field defensively (1B, 2B, SS, 3B and all three outfield spots). Over one six-year stretch with the Rays, Zobrist accumulated 37.5 WAR and led all position players in baseball with 8.7 WAR in 2011.

5 Anthony Rizzo and Zach Cates for Andrew Cashner and Kyung-Min Na

Kamil Krzaczynski-USA TODAY Sports

Rizzo has been a beast in the middle of the Chicago Cubs’ lineup over the past two-plus seasons. His OPS+ over that time is right around 150 and he is currently on pace to set personal bests in homers, hits, runs, RBI, doubles, triples, walks and total bases. With runners in scoring position this season, he has an OPS of 1.128. At just 26 years of age, Rizzo has already developed into one of the best hitters in the sport and with 4.7 WAR already in 2016, is on the short list for league MVP. In 2012, the Padres sent him to Chicago for starting pitcher, Andrew Cashner. Unfortunately for San Diego, he never developed into the pitcher they had hoped he’d become and was dealt to Miami just prior to this year’s trade deadline. In 130 appearances (97 starts) with the Padres, he was just 28-43 with a mediocre 98 ERA+.

4 Bartolo Colon and Tim Drew for Cliff Lee, Brandon Phillips, Grady Sizemore and Lee Stevens

Noah K. Murray-USA TODAY Sports

Sometimes, a team is willing to give up a prospect with All-Star potential in order to acquire a veteran who will significantly increase the club’s chances of advancing deep into the postseason. Occasionally, surrendering two potential stars may be worth it. Montreal, however, in its quest to land Bartolo Colon for a handful of starts down the stretch of the 2002 season, gave up a package of players who would combine for 10 All-Star Game appearances over their careers. Though Phillips wouldn’t get much playing time until he was eventually traded to the Reds in 2006, Sizemore became the Tribe’s starting centerfielder when he was just 22 years old. During his first four years as a full-time player, he posted 24.6 WAR and had at least 20 home runs, 100 runs, 75 RBI and 20 stolen bases each season. Cliff Lee went 83-48 for Cleveland and won the 2008 A.L. Cy Young Award (22-3, 2.54 ERA). Colon, for his part, pitched well for the Expos, going 10-4 with a 3.31 ERA over 17 starts during his half-season in Canada. However, Montreal finished the year a distant 12 ½ games out of a playoff spot.

3 Jose Bautista for Robinzon Diaz

Troy Taormina-USA TODAY Sports

It took Bautista a long time to land on his feet in baseball. In 2000, he was drafted by Pittsburgh in the 20th round and was then taken by Baltimore in the 2003 Rule 5 Draft. The following year, he was waived and subsequently claimed by Tampa Bay, his contract was purchased by Kansas City and he was then dealt to the Mets and then back to Pittsburgh. Bautista played in 400 games and posted a 91 OPS+ for the Bucs over parts of five seasons. Toronto acquired him in a 2008 mid-season trade and, after putting up average numbers during his first year-and-a-half there, he exploded for 54 home runs in 2010. Joey Bats, as he’s now known, was born. In his time with the Jays, he has an OPS+ of 146 with 258 long balls. Diaz was out of baseball before he was 26, finishing with a home run and 39 hits in 148 plate appearances.

2 Adam Jones, Chris Tillman, Tony Butler, Kam Mickolio and George Sherrill for Erik Bedard

Tommy Gilligan-USA TODAY Sports

In 2007, the Seattle Mariners won 88 games and then acquired Erik Bedard in the off-season to solidify their starting rotation. Bedard had gone 28-16 over the prior two seasons in Baltimore, but he was hit with injuries during his time in the Northwest. He missed the entire 2010 season and made only 46 starts for the M’s, posting a 123 ERA+, while winning just 15 games. In the trade, the Orioles received outfielder, Adam Jones and starting pitcher, Chris Tillman, along with a few other minor players. Jones has become a fixture at or near the top of the O’s lineup. He’s made five All-Star teams during his time in Baltimore, hitting 220 home runs and accumulating over 700 runs and RBI. Tillman, meanwhile, has won at least 10 games four years in a row and has compiled a career record of 71-47. He is currently tied for third in the A.L. this season with 15 wins.

1 Miguel Cabrera and Dontrelle Willis for Cameron Maybin, Andrew Miller, Dallas Trahern, Burke Badenhop, Frankie De La Cruz and Mike Rabelo

Rick Osentoski-USA TODAY Sports

The Marlins knew they were giving up a superstar when they dealt Cabrera to the Tigers after the 2007 season. “Miggy” was just 24 at the time and had already launched 138 homers and posted an OPS+ of 143 during his first five MLB years. The move was a cost-cutting measure for the budget-conscious Marlins, but they got virtually nothing in return for what turned out to be one of the best hitters of his generation. In Cabrera’s nine years with Detroit, he has won two MVPs, four batting titles and a Triple Crown (baseball’s first since Boston’s Carl Yastrzemski accomplished the feat in 1967). This trade was so one-sided, it easily sits atop this list, even though Willis actually had a negative impact on the Tigers (2-8 record, 6.86 ERA). While Maybin had been a top-10 MLB prospect, he’s never realized his potential. He’s posted an OPS+ of 92 while bouncing around several teams over the years. Miller has become an elite relief pitcher, but only after he was flipped to Boston for Dustin Richardson, who never even played for Florida.

Give TheSportster a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheSportster?

Get Your Free Access Now!

More in MLB

Top 25 Most One-Sided MLB Trades Involving Active Players