General managers are paid huge salaries to crunch numbers, rate prospects, and work out deals that will put their teams in a better position to win. Unfortunately, even a transaction that looks great on paper can have disastrous (and potentially hilarious) consequences.

That’s the saddest thing about front-office mistakes — at some point, an organization’s brightest minds were convinced that they were getting the better deal. Still, bad trades aren’t just embarrassing. They have the potential to ruin a team’s championship fortunes for years to come. Let’s climb up on our high horses and take a look at five trades that never should have happened.

1996: Hornets Trade Kobe Bryant

Kobe Bryant

As the first guard ever to be drafted out of high school, 17-year-old Kobe Bryant entered the NBA to a considerable amount of fanfare. Impressed by a pre-draft workout, Lakers general manager Jerry West decided to work out a deal with the Charlotte Hornets to acquire Bryant’s services. Charlotte drafted Kobe with the 13th pick and immediately shipped him off to the Lakers in exchange for Vlade Divac, a journeyman center known more for his flopping than his rebounding. Kobe has won five rings and an MVP award as a Laker, while the Hornets’ biggest move was relocating to New Orleans.

1989: Walker Gets Dealt For a Dynasty

Herschel Walker

In 1989, the Minnesota Vikings were so sure that Herschel Walker would lead them to a Super Bowl that they traded away their future to get him. In total, the Cowboys acquired five players and six future draft picks in exchange for their star running back. Walker wasn’t the same player in Minnesota, failing to break the 1,000-yard plateau during his two-and-a-half seasons as a Viking. Meanwhile, the Cowboys used their picks to acquire Hall of Famers Emmitt Smith and Darren Woodson, a pair of key components of the team’s 1990s dynasty.

1971: Nolan Ryan’s Wild Start

Nolan Ryan

When a trade is singled out as the worst transaction in New York Mets history, it’s safe to say it was a catastrophe. Frustrated by their young flamethrower’s control issues and general lack of progress, the Mets shipped him off to the California Angels for All-Star shortstop Jim Fregosi. Fregosi’s career tailed off with the Mets, while Ryan went on to amass over 300 wins, seven no-hitters, and a MLB-record 5,714 strikeouts. Judging by the some of the New York’s recent front-office debacles, they still haven’t learned their lesson.

1983: Elway Passed to Denver

John Elway

Stanford product John Elway was the Andrew Luck of his day — a mobile, rocket-armed quarterback who was considered a “can’t miss” NFL star. In the weeks leading up to the 1983 NFL Draft, Elway made it clear that he wouldn’t play for the Baltimore Colts, prompting the hapless squad to trade the first overall pick to Denver for a backup quarterback and a pair of offensive linemen. Elway led the Broncos to a pair of Super Bowl wins during his Hall of Fame career, while the Colts wallowed in mediocrity until another “can’t miss” quarterback came along. In the Colts’ defense, Elway didn’t give them much of a choice in the matter — he threatened to switch to baseball if he wasn’t traded.

1919: The Curse of the Bambino Begins

Babe Ruth

Ask any baseball fan about the worst trade in baseball history, and they’ll refer you to this 1919 disaster. At the time, Boston Red Sox star Babe Ruth had recently transitioned from the mound to the outfield, hitting a record 29 home runs and cementing his status as a marquee ballplayer. After his record-breaking season, Ruth demanded a $20,000 raise, which the cash-strapped owner Harry Franzee refused to pay. Instead, the Sox shipped the Babe off to New York for $125,000 cash and an additional loan that Franzee needed to fund his Broadway play. And the rest, as they say, is history.

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