The trade is one of the biggest risks in all of baseball. Every scout and general manager knows that. Make a good one and you’ve got a mega-star who leads you to a championship and huge returns. Make a bad one and not only does your team slump but you might well be out of a job. So many times in baseball has a team made what they thought was the brilliant team of a lifetime only for it to blow up in their face. They go for a guy who looks experienced only to realize he was on the downside of his career. They pass on an untested rookie and see him turn into a legend. And some guys just don’t fit in with their new unit nearly as well as were expected.
It’s far from an exact science as it takes a while for some players to unlock their greatness. Other times, it was obvious to everyone but their own teams. A few cases of trades were just rough, a team slumping and seeing someone else benefit. Other times, the trade was an absolute flop that caused years (or decades) of heartbreak while the other side turns into a dynasty. While every team has a half-dozen or more of these deals, they always have one that stands out. One trade that becomes legendary as the worst. Here is the one trade every MLB team wishes they could take back to show the risks of this abounding to this day.
30 Arizona Diamondbacks - Trading Carlos Quentin
The Diamondbacks haven’t had too many horrible trades over the years. But Carlos Quentin has to stand out. In just two seasons, he’d done good work but hampered by an injury in 2007. Thus, Arizona decided to trade him to the White Sox for Christopher Carter.
Quentin would soon be a star for Chicago, becoming one of the team’s best hitters and an All-Star.
He hit a bit of a slump but still remained strong and clearly a slugger Arizona could have used.
Carter wouldn’t even play for Arizona while Quentin has played for the Sox and Padres among others to show this was a bad move for Arizona.
29 Atlanta Braves - Sending Adam Wainwright To St. Louis
True, the Braves have made a few bad moves over the years yet Adam Wainwright has to stand tall. The Braves drafted him in 2000 with a nice $1.2 million contract and Wainwright showed promise in the minors. However, just before he could start in the main roster, Wainwright was part of a multi-player trade that sent him to St. Louis.
Wainwright has since become one of the best pitchers in Cardinals history, second only to Bob Gibson in strikeouts. He’s twice led the National League in wins and part of the Cardinals’ 2006 World championship team. Given their rough times with pitchers since that deal was made, Atlanta would have been better off keeping Wainwright.
28 Baltimore Orioles - Trading Curt Schilling
This is one of the no-brainer choices on this list. Nothing riles up Baltimore fans more than this terrible deal that hit the team hard. Convinced that Glenn Davis would be the future of the organization, the Orioles traded pitchers Curt Schilling and Pete Harnisch and outfielder Steve Finley to the Astros for him. In spring training, Davis had a neck injury that was the harbinger for a forgettable run in Baltimore. He was never the hitter they wanted and not helped by antics like getting his jaw broken in a bar fight. Meanwhile, of the three traded off, the biggest would be Schilling, later the hero of the Red Sox’s 2004 championship team. It’s been a long time but Orioles fans still grouse on this.
27 Boston Red Sox - Babe Ruth
They’ve done well in the last 15 years with three World Series and several playoff runs. But the Boston faithful have never forgotten this deal which began the most infamous “curse” in sports history.
Harold Frazee is still loathed for how, to pay off personal debts, he sold Babe Ruth to the Yankees for $125,000.
Ruth was already showing his promise as a once-in-a-lifetime player who brought the Red Sox to prominence. Fans were upset but few truly realized the damage that was done. Ruth would push New York to prominence and help create the Yankees dynasty while the Red Sox spent decades without a title. No wonder it’s still hailed as a landmark move in baseball history.
26 Chicago Cubs - Sending Lou Brock To St. Louis
Ask any Cubs fan and they’ll agree that their own “curse” would have ended a lot sooner without this deal. In 1964, the Cubs were doing well but figured they needed more power. So, they struck a deal with the Cardinals for promising pitcher Ernie Broglio in exchange for rookie Lou Brock. Brogilio turned out to be injury riddled and his win-loss record sank before he was out of baseball in two years. Meanwhile, Brock erupted into an instant star in St. Louis. It was thanks to his hitting and base-stealing that the Cardinals won the pennant and then the World Series. Two more pennants and another World championship followed with Brock one of the greats of his time. The Cubs were good in this period but this trade kept them from getting to the top.
25 Chicago White Sox - Getting Rid Of Sammy Sosa
Fans outside of Chicago don’t understand the deep-set rivalry the Cubs and White Sox faithful have with each other. Thus, it really galled the White Sox when Sammy Sosa turned into a powerhouse for their cross-town rivals. To be fair, while showing good hitting with the White Sox in the early ‘90s, Sosa also struck out a lot and hit a poor slump in 1991. Thus, the Sox thought it would be good to unload him to the Cubs in exchange for George Bell.
It took a bit but Sosa was soon one of the powerhouse hitters of the majors.
The highlight was 1998 as he and Mark McGwire had their home run chase that livened up baseball. DSosa remains a beloved Cubs figure which aggravated those on the South Side.
24 Cincinnati Reds - Frank Robinson To BAL
Even the movie “Bull Durham” had to note this as one of the worst trades in baseball history. Frank Robinson had been a solid player for a decade for the Reds, a fantastic hitter, NL MVP and good in the outfield. But in 1965, he was traded to Baltimore for Milt Pappas as Oriole management considered Robinson “an old 30.” It took no time for Cincinnati to regret it.
In his very first season with his new team, Robinson won the Triple Crown, was named AL MVP (still the only man to achieve that honor in both leagues) and powered the Orioles to their first World Series. Robinson would go on to help Baltimore to three more pennants and another World Series and become the first black manager in the majors. Pappas, meanwhile, would be a footnote to this lopsided trade.
23 Cleveland Indians - Trading Rocky Colavito
To Indians fans, their decades of woe can be traced to this deal. Colavito was easily Cleveland's most popular player in the 1950s team. In 1959, he led the AL in home runs, including four in one game. He loved the town and would spend hours after games signing autographs for fans. That’s why it was so outrageous when the Indians traded him in 1960 to the Tigers for Harvey Kuenn.
General manager Frank Lane was slammed for the move, not helped by his line “I traded hamburger for steak.” The Indians went into a serious slump after that while Rocky struggled to reach the same numbers in Detroit. He returned to the Indians in 1965 and did well but giving him away as he was hitting his peak is a key reason trading Rocky was terrible for Cleveland.
22 Colorado Rockies - Trading Andy Ashby and Brad Ausmus
As a newer team, the Rockies don’t have the long history of terrible trades as other teams do. Still, this deal has to rank as a major one. In 1993, their third year of existence, the Rockies were trying to beef up their roster more. Andy Ashby was 0-4 as a pitcher while Brad Ausmus was still in the minor leagues. The Rockies sent both to the Padres in exchange for Bruce Hurst and Greg Harris.
The veteran Hurst was in the downside of his career and lasted just one season while Harris had a forgettable run.
Meanwhile, Ashby turned into a great worker who helped the Padres reach the 1998 World Series. Ausmus would bounce around the league but also win three Golden Glove awards and show how the Rockies gave away two guys who could have helped.
21 Detroit Tigers - Trading A Young John Smoltz
John Smoltz should have been a true success story for the Tigers. A Detroit native, he’d grown up loving the team and naturally jumped at the chance to play for them. But before he could start in 1987, the 20-year old was traded to Atlanta for veteran Doyle Alexander. While he helped the Tigers win the division, Alexander would be out of baseball in just two more years.
Meanwhile, Smoltz became a cornerstone of the Braves’ powerhouse team of the ‘90s, twice leading the NL in wins and strikeouts, a Cy Young winner and part of Atlanta’s 1995 championship team. He was easily elected to the Hall of Fame as one of the best pitchers of his time which could have been Detroit’s to boast.
20 Houston Astros - Giving Up On Joe Morgan
Reds fans are utterly grateful for the foolishness of the Astros. Joe Morgan had been rising up in Houston going back to when they were the expansion .45s. He was a good hitter but manager Harry Walker considered him to be a bad locker room influence. So in November of 1971, Morgan was part of a major multi-player deal with the Reds. The Astros didn’t benefit very well, slumping down badly and spending a few seasons mired in losses. Morgan turned out to be the perfect fit for what would become the Big Red Machine. In 1975 and 76, he was the NL MVP with the Reds winning the World Series both seasons. Morgan returned to Houston in 1980 but giving him away was one of the worst moves of Astros lore.
19 Kansas City Royals - Ship David Cone After World Series Win
There’s always a danger of teams after they win a World Series to make some moves that backfire. Such a case was after the Royals won in 1985. David Cone had been a good pitcher for them but the Royals wanted more firepower. In 1987, they reached a trade with the Mets who already were reacting to their own World Series win.
Cone was sent to New York for Ed Hearn, Rick Anderson and Mauro Gozzo.
None of those three would make any real impact as the Royals slumped badly. Cone would bounce about from New York to Toronto and a brief return to Kansas City. He truly found his groove with the Yankees, winning four World Series and a perfect game. It just shows how unloading talent after a championship is a risk.
18 Los Angeles Angels - Giving Up On Devon White
Drafted by the Angels in 1981, it took six years for Devon White to prove himself as a player. He began rising up nicely with his hitting and great speed and famous for stealing all the bases on the way to a run. He was popular with fans it looked like he could help the Angels be contenders. Instead, in 1990, White and Devon Frasier were sent to Toronto for Junior Felix and Luis Sojo. Both lasted barely two years with no impact. White took well to Toronto, winning back-to-back World Series with the team. He won another with the Marlins in 1997 and showed the Angels made a very unheavenly move giving him up.
17 Los Angeles Dodgers - Pedro Martinez For Delino DeShields
In 1988, the team had been enjoying a World Series win so few paid attention to their signing of a young Pedro Martinez. He showed his skills in the minors and promoted to the main roster. But, laughably, Tommy Larsoda questioned Martinez’s stamina. So in 1992, they traded him to the Expos for Delino DeShields. There, Martinez blossomed into a great pitcher that helped Montreal out. He then joined the Red Sox to become a hero of the 2004 World Series campaign, winning the Triple Crown in 1999 and three Cy Young awards. Now in the Hall of Fame, Pedro shows a major “give away a star” move by the Dodgers.
16 Miami Marlins - Miguel Cabrera Moved As Part Of Fire Sale
Miguel Cabrera had a great rookie season in 2003 as he joined the Marlins in time to enjoy a World Series victory. He continued to be an All-Star with good work and a powerful hitter.
But then in 2007, the Marlins entered one of their periodic “house cleaning” phases and decided to get rid of Miguel and his big contract.
So he and Dontrelle Willis were given to the Tigers in exchange for a half-dozen players.
After getting a big contract, Cabrera took off wonderfully as a major hitter, winning the Triple Crown in 2012, four-time batting champion and twice AL MVP. Miami has suffered badly to show how trading for so many guys doesn’t make up for giving away a huge star.
15 Milwaukee Brewers - Giving Up On Gary Sheffield
Gary Sheffield was seen as one of the best hitters of his time. Just a teenager when he debuted in 1988, Sheffield was soon notable for his great speed and improving his hitting. However, Sheffield was making noises in the clubhouse about management being biased against him and not making friends. Thus, the Brewers thought they’d be better off trading him to the Padres for Ricky Bones, José Valentin, and Matt Mieske.
Sheffield was immediately the NL batting champion and showed great improvement. In 1993, he joined the Marlins for a good All-Star run that included winning the World Series in 1997. While he moved to other teams, Sheffield showed that letting him go just as he was about to hit his stride was a dumb move for Milwaukee.
14 Minnesota Twins - Bert Blyleven
Right now, Twins fans know Bert Blyleven as a color commentator. That’s ironic given how he’s also a terrible trade for the team twice over. He started in 1970 and soon showed his skills as a fantastic pitcher. However, he wasn’t happy with his salary and so in 1976 was part of a multi-player trade to the Rangers. He didn’t last long before going to the Pirates where he won a World Series.
After a stint with the Indians, the Twins traded to get Blyleven back. On the one hand, he was part of their 1987 championship team. On the other, he allowed 96 runs over two seasons. So in 1988, the Twins traded Blyleven again, this time to the Angels. So as much as the Twins love to talk of their Hall of Fame favorite, they also handed him off a few times.
13 New York Mets - Trade Tom Seaver, Rather Than Pay Him
It’s a trade so epic that it created one of the biggest fan revolts in baseball history. Tom Seaver had easily been the star for the Mets, “The Franchise” notable for his fantastic pitching. He was a key reason the Mets went from jokes to 1969 World champions and fans loved to watch him play. With three Cy Young awards and numerous strikeout records, Seaver naturally thought asking for more money was logical.
The Mets disagreed and so, in what was called “The Midnight Massacre”, they made Seaver part of a big trade with the Reds.
The next day, the Mets front office was crammed with fans returning torn-up season tickets and massive booing at games. Seaver helped the Reds out and had a brief return to the Mets in 1983 before retiring as a legend the Mets tossed aside.
12 New York Yankees - Trading Fred McGriff
Usually, the Yankees benefit from a trade with another team. However, Fred McGriff was a major miss for them. He signed with them in 1981 but before he could really play, he was part of a multi-player trade to Toronto. The Yankees spent that decade mired near the bottom of the division with little to cheer about. Meanwhile, McGriff would go on for a fantastic career with just under 2500 hits and nearly 500 homers. He played for several teams, twice leading the league in home runs and a 5-time All-Star. The height of his career was winning a World Series with the Braves in 1995 and show a rare case of the Yankees letting a star get away from them.
11 Oakland Athletics: A's Won't Pay Reggie Jackson
As soon as he debuted in 1967, Reggie Jackson was a clear superstar in the making. Jackson was the key figure in the A’s dynasty that won five straight divisional titles and three straight World championships. Jackson was named MVP in 1973 and clearly loved Oakland. However, with free agency coming, Jackson held out for more money from owner Charles Finley. Finley refused and instead made Jackson part of a big trade to Baltimore.
That move basically destroyed the A’s dynasty and led to their downfall. Jackson would end up with the Yankees and the star of the 1977 World Series with another championship the next year. Jackson wrapped up his career in Oakland but giving him away in the first place turned the A’s into F’s.
10 Philadelphia Phillies - Ryne Sandberg Sent To Chicago
Sandberg was an okay player for Philadelphia, showing promise but the front office finding him untested. So they went to the Cubs and dealt both Sandberg and veteran Larry Bowa for shortstop Iván DeJesús.
DeJesus would do almost nothing for Philadelphia who slumped badly.
Meanwhile, Sandberg was the shot in the arm the Cubs needed, exploding in 1984 as MVP and leading the Cubs to their first NL Central title. A 10-time All-Star with nine Golden Gloves and seven Silver Sluggers, Sandberg is in the Hall of Fame as one of the best hitters of his time. Ironically, he managed the Phillies in 2013-15 as if to remind them of what they gave away.
9 Pittsburgh Pirates - Aramis Ramirez To Chicago
The Dominican Republic born player signed with the Pirates in 1994 and was the youngest starting player in the majors in 1998. He did struggle for a bit and sent to the minors so the Pirates didn’t see much promise in him. Thus, they traded Ramirez off to the Cubs with Kenny Lofton for Jose Hernandez, Matt Bruback and Bobby Hill. After a rough start, Ramirez was soon a top hitter for the Cubs, a three-time All-Star who won the Silver Slugger award in 2011. Ramirez would end his career with the Pirates in 2015 yet seeing how terrible Pittsburgh was in the 2000s, keeping the great hitter Ramirez would become was a terrible move.
8 San Diego Padres - Ozzie Smith
From his debut, Ozzie Smith was showing incredible skills for the Padres with his speed allowing him to make terrific plays. He was popular with the fans and looked the star the team needed. But Smith had issues with management to the point of taking out an ad in the San Diego newspapers offering his services to other teams.
Figuring they were better off without the headache, the Padres shipped Smith to the Cardinals as part of a big player deal.
Once there, “the Wizard of Odds” became a St. Louis icon. His great play, bright smile and astounding backflips made him a huge favorite with fans. A 15-time All-Star, Smith helped the Cardinals win the 1982 World Series and 1985 NLCS.
7 San Francisco Giants - Gaylord Perry To Cleveland
Throughout his career, it was no secret that Gaylord Perry was one of the biggest spitball throwers in the game. He reached a peak in 1971 with the Giants winning the division. Which was why it was so stunning when Perry was traded to the Indians with Frank Duffy for promising starter Sam McDowell. McDowell had just one bad season in San Francisco and ended up winning just 24 games for the rest of his career. Perry won 180 over several teams with two Cy Young awards. Thus, giving him away was a reason the Giants failed to take off in the ‘70s.
6 Seattle Mariners - David Ortiz
The Mariners listed the man as David Arias when they signed him on in 1992. Through the next few years, he was impressing scouts. Alex Rodriguez was one of many Mariners players telling the coaches that calling up Ortiz would help the team out majorly. Instead, they decided to use him to complete a transaction with the Twins.
Ortiz had good numbers in Minnesota but, to cut costs, the Twins released him in 2002. Thanks to old friend Pedro Martinez, Ortiz landed a contract with the Red Sox. “Big Papi” is now a Red Sox icon, a key factor in Boston winning three world championships and MVP of the 2013 Series. He’s a lock for the Hall of Fame and rocking Seattle fans on letting Ortiz go before he took off.
5 St. Louis Cardinals - Steve Carlton To Philly
Steve Carlton lucked out joining the Cardinals in 1967 just as “El Birdos” were turning into a powerhouse. They won back to back pennants and the ’67 World Series with Carlton showing his skills as a pitcher. However, Carlton had beef with management over his play and so just before the 1972 season, he was traded to the Phillies for Rick Wise. Wise would last just one season in St. Louis with little effect.
Carlton became a star for the Phillies, winning the Triple Crown in his first season.
He would add four Cy Young awards, lead the NL in strikeouts five seasons and won another World championship in 1980. The Cardinals spent much of the ‘70s in the lower ranks of the National League and the giving away of Carlton is a reason why.
4 Tampa Bay Rays: Bobby Abreu Flipped To The Phillies
After a brief stint with the Astros, Bobby Abreu was taken in the 1997 expansion draft by the newly created Rays. Within hours, the Rays flipped him over to the Phillies in exchange for Kevin Stocker. Stocker would have okay but not good numbers and be off the Rays in just two seasons. Abreu was soon the star of the Phillies' offense, putting up fantastic numbers with runs at the batting title and a two-time All-Star. It may make an odd bit of sense that the Rays’ very first trade also has to rank as their absolute worst to lose what could have been their first major star.
3 Texas Rangers - Ron Darling To The Mets
You could understand the thinking at the time. But it’s since turned into a massive error for the Rangers. Ron Darling debuted in the minors in 1981 and was soon having a very poor career with mediocre numbers. Thus, the Rangers figured it was better to trade him and Walt Terrell to the Mets in exchange for Lee Mazzilli.
Mazzili would have little success in Texas and be handed to the Yankees at mid-season.
Darling nicely improved and soon became a key to the Mets’ bullpen. In 1986, he was part of the epic Mets team that won the World Series and while not Hall of Fame standards, still a great pitcher. Ironically, on that ’86 team, he was joined by none other than Mazzilli to rub the bad trade in Texas’ face even more.
2 Toronto Blue Jays - Getting No Big Piece In Return For Roy Halladay
You knew this was coming. The Blue Jays have made their share of very bad moves from letting guys go to passing on future stars. But absolutely nothing drives the Blue Jays fanbase crazy more than this. Throughout the 2000s, Halladay had been the star ace for the Blue Jays. But for some reason, Toronto decided to hand him off to the Phillies for Travis d'Arnaud, Kyle Drabek, and Michael Taylor.
Toronto fans were upset then and worse when all three of those guys faltered. In his first year in Philadelphia, Halladay won another Cy Young, again led the league in wins and pitched both a perfect game and a post-season no-hitter. While injuries cut his career short in 2013, Halladay proved how his exit was the worst deal for a deal that specializes in them.
1 Washington Nationals - Jonathan Papelbon
If we were to go back to the days of the Montreal Expos, there are plenty of bad trades to mention, but we'll be sticking with the Nationals' history in Washington. The Nats were looking for a closer and got the once dominant Jonathan Papelbon. The Nats sent Nick Pivetta and cash to Philadelphia, which wasn't a big loss for Washington, but Papelbon came in and not only disappointed on the mound, but created problems in the Nats' dugout. Just a disaster all around.