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.