The 5 Worst MLB Trades Since 2000

Being a general manager in sports is hard. Like very hard. However, as many good moves as one may make, he will always make at least a handful of bafflingly bad moves along the way.

In my humble opinion, being an MLB GM, President of Baseball Operations, or whatever position is making moves on any given club, is one of the hardest jobs in sports. There are so many players within each organization that one wrong move could cost you a future superstar for a one-year rental. 

So, with MLB free agency rumors at a standstill, I figured it would be interesting, using the power of hindsight, to make fun of some general managers for some of the most boneheaded trades since the year 2000.

Yes, I know most of the dumbest moves in MLB history happened before the turn of the century, but everyone knows those ones. Just for the sake of history I’ll acknowledge Pedro Martinez traded to the Expos and later the Red Sox for absolute squat, Nolan Ryan to the Angels for Jim Fregosi, John Smoltz to the Braves for Doyle Alexander, Tom Seaver to the Reds for a handful of nothing, and, of course, Babe Ruth to the New York Yankees.

Now that those are out of the way, let’s begin.

Indians trade Bartolo Colon to Montreal Expos for Cliff Lee, Grady Sizemore, and Brandon Phillips

Photo By Getty Images

Back before he was a meme, Bartolo Colon used to be a really good pitcher, and was young too! Back in 2002, with the club on the verge of being contracted entirely, Expos ownership decided to go for broke and trade for the then 29-year-old Colon to push for the playoffs. They gave up a seemingly low-risk trio of prospects to try to win right then.

The only problem was that those prospects turned into things that the Expos desperately needed to keep the team in Canada. Grady Sizemore turned into a multiple time All-Star and heart-throb for the ladies of Cleveland. Brandon Phillips became one of the most fun players to watch in all of baseball, as well as a four-time Gold Glove winner and two-time All-Star. Then there’s Cliff Lee, who only became a Cy Young winning pitcher. Colon was out of Montreal by 2003, and the team moved to DC after the 2004 season. Ouch.

Texas Rangers trade Mark Teixeira to Atlanta Braves for Matt Harrison, Elvis Andrus, Neftali Feliz, Jarrod Saltalamacchia, and Beau Jones

Photo by Fort Worth Star Telegram

Hey, it’s Mark Teixeira again. Teixeira was great during his 4fouryears with the Rangers, winning a Silver Slugger twice and a Gold Glove by the age of 26. The Braves were in the playoff hunt in 2007 so, similar to the Expos, decided to go for it all. They sent five minor leaguers to the Rangers in the hopes of winning it all. It didn’t work. The Braves missed the playoffs and traded Teixeira to the Angels the next year. So what did they give up for a year of ‘meh’? Just a core of players that would help the Rangers get to back to back World Series.  Matt Harrison was one of the Rangers key starters during their run of dominance and became an 18 game winner. Neftali Feliz won the AL ROTY in 2010 and saved 72 games in 2010-11 before blowing out his arm and fading into obscurity. Jarrod Saltalamacchia won a World Series with the Red Sox in 2013. Probably could’ve used some of those guys, huh Atlanta?

Philadelphia Phillies trade Curt Schilling to Arizona Diamondbacks for Omal Daal, Vicente Padilla, Travis Lee, and Nelson Figueroa

Photo by Stephen Dunn/Getty Images

This is one of those trades when giving up a king’s ransom of prospect just to get “the guy” works out. Schilling turned into one of the best pitchers in baseball, at the age of 34 nonetheless, once arriving in the desert. He would be named Cy Young runner-up twice and help lead the Diamondbacks to a World Series title, where he and Randy Johnson would win World Series co-MVP. With the exception of Vicente Padilla, who was okay at best, none of the return pieces for the Phillies filled the void left by Schilling. 

San Francisco Giants trade Joe Nathan and Francisco Liriano to Twins for AJ Pierzynski

Minnesota Twins v New York Yankees, Game 2
Photo by Jim McIsaac- Getty Images

AJ Pierzynski had a very good start to his career in Minnesota, hitting .301 over his first 6 years for the Twins and earned an All-Star appearance in 2002. The Twins knew they didn’t want to pay the upcoming free agent, so they sent him to the Giants for two young arms.

Liriano never truly realized his potential and was repeatedly caught by the injury bug, but when healthy, he pitched at an ace level during his time in Minnesota. Nathan would become arguably the best closer of the 2000s not named Mariano Rivera, saving a total of 377 games, good enough for eighth all-time. He would also be a six-time All-Star and twice received Cy Young consideration for closing games. The Giants definitely could’ve used one of the best closers of all time instead of AJ Pierzynski, who was out of San Fran by 2005.

Florida Marlins trade Miguel Cabrera and Dontrelle Willis to Detroit Tigers for Cameron Maybin, Burke Badenhop, Andrew Miller, Mike Rabelo, Dallas Tehran, and Eujolio De La Cruz

Photo from Cabrera’s Instagram

I shouldn’t have to say anything, but I must. The Florida Marlins traded away a 24-year-old BEFORE HIS PRIME Miguel Cabrera for what ended up being a bag of balls. It doesn’t matter what the Marlins got in return because they gave up the best pure hitter of the 2000s.

Cabrera went on to be a seven-time All-Star, five-time Silver Slugger winner, four-time batting champ, two-time home run champ, two-time MVP, and the 2012 Triple Crown winner. This is easily the worst trade of the last 20 years. This was egregiously stupid and I can’t believe it isn’t talked about more. The Marlins are a joke. Delete the franchise.

Photo: Smithsonian Magazine



Leave a Reply

Powered by

Up ↑

%d bloggers like this: