The Top 12 Head-Scratching Trades in Baseball History

By now you’ve probably heard about the epic blockbuster Miami fire sale that sent Jose Reyes, Josh Johnson, Mark Buehrle, Emilio Bonifacio, and John Buck to Toronto for Yunel Escobar, Adeiny Hechavarria, Henderson Alvarez, Justin Nicolino, Jake Marisnick, Jeff Mathis and Anthony DeSclafani. And, you’re probably thinking what we are. Who are these guys that the Blue Jays are sending to the Marlins? Besides Yunel Escobar, we’re not familiar with many of these players involved in the deal. Naturally, it sounds like a lopsided deal.

However, some of the prospects heading to Miami could actually become quality players. And, the big names going to Toronto could flounder. Long story short, until baseball resumes next season, no one knows how this trade will actually play out. Regardless, this deal is a head scratcher, which got us thinking about other questionable baseball trades.

So, here they here. The top 12 head scratching trades in baseball history.

12. November 29, 1971

The Cincinnati fans and press weren’t too happy when the Reds sent Lee May, Tommy Helms, and Jimmy Stewart to the Astros for Jack Billingham, Ed Armbrister, Cesar Geronimo, Denis Menke, and Joe Morgan. However, the addition of Morgan, Geronimo, and Billingham were key pieces of the ‘Big Red Machine’ with ten straight winning seasons, two world championships, three league championships, and five division titles.

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11. November 10, 2008

Colorado made out like bandits when they had a trade with Oakland involving Matt Holliday for Carlos Gonzalez, Huston Street and Greg Smith. Holliday spent only 93 games with the A’s before being shipped off to St. Louis. Meanwhile, CarGo and Street found success with the Rockies. In short, Colorado essentially got two great players for several players that no one remembers.

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10. December 5th, 1984

When the Yankees traded Stan Javier, Tim Birtsas, Jay Howell, Eric Plunk and Jose Rijo to the Oakland Athletics for Rickey Henderson, Bert Bradley, and cash, it pretty much laid the groundwork for the prospects-for-superstar-entering-free-agency trade.

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9. December 10, 1971

Mets fans probably still cringe at the mention of this trade. While Jim Fregosi was a solid player for the California Angels, New York gave up a number of players, including Nolan Ryan, Frank Estrada, Don Rose, and Leroy Stanton, for a player that wouldn’t live up to that potential. And, while Ryan wasn’t the player that would eventually strike fear in batters around the league, it’s unbelievable that any team would trade him away.

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8. December 4, 2007

Miami had to send Miguel Cabrera, along with pitcher Dontrelle Willis, to Detroit in 2007. However, the 2012 Triple Crown winner is arguably the best player in the game. But, the fact that the Tigers got Miggy for Dallas Trahern, Cameron Maybin, Burke Badenhop, Eulogio De La Cruz, Andrew Miller and Mike Rabelo just seems unfair.

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7. August 30, 1990

When the Red Sox sent Boston native Jeff Bagwell to Houston for veteran pitcher Larry Andersen, it made sense at the time. Boston had Wade Boggs and needed Anderson for a playoff run. Today, however, this trade sounds insane. Bagwell would go on to have a stellar Hall of Fame worthy career with the Astros and Larry Anderson would only play 15 games for Boston.

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6. December 5, 1990

The Sporting News called the San Diego Padres trading Roberto Alomar and Joe Carter to the Toronto Blue Jays for Fred McGriff and Tony Fernandez the “trade for the ages”. Why? Because in terms of Win Shares and Win Shares Above Bench (WSAB), this trade was actually the greatest exchange of premium talent.

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5. May 25, 1989

The Montreal Expos trade of Randy Johnson, Brian Holman and Gene Harris to the Seattle Mariners for Mark Langston and Mike Campbell was completely lopsided at the time. Langston did rather well for Montreal and they didn’t know what kind of pitcher Randy Johnson would become. In hindsight, it’s unbelievable that the Expos gave up the future Hall of Famer.

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4. January 27, 1982

Some Philly fans may still not have gotten a handle on this trade. The Phils sent veteran Larry Bowa and a kid named Ryne Sandberg to the Cubs for a mediocre second baseman in Ivan de Jesus. Overall, this move is just confusing. It’s not like de Jesus was really good at the time, so why ship off a future Hall of Famer?

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3. June 27, 2002

Before Montreal moved the franchise to Washington, they were trying to make their way up the standings in the NL East. So, they decided to give up a number of future All-Stars for pitchers Bartolo Colon and Tim Drew to the Indians. In return, Cleveland received Grady Sizemore, Brandon Phillips, Cliff Lee, and Lee Stevens. While Phillips didn’t hit his stride until he went to Cincinnati, it’s mind boggling that Montreal gave up this group of players for Bartolo Colon.

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2. January 10, 1991

Baltimore essentially gave up the farm in Steve Finley, Curt Schilling, and Pete Harnisch to Houston for Glenn Davis. Finley became the big bat for Houston, while Schilling would go on to have a Hall of Fame career and Harnisch would become an All-Star for the Astros. As for Davis, he never really amounted to much for the Orioles.

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1. August 25, 2012

When Boston sent Josh Beckett, Adrian Gonzalez, Carl Crawford and Nick Punto to the Dodgers it broke a number of baseball records. For example, it was the first time that two players (Crawford and Gonzalez) with $100 million contracts were part of the same trade. And, with the acquisition of the former Red Sox players, the Dodgers added an astounding $250 million to their payroll. This means that L.A. added more salary in one transaction than any other team in baseball’s long history.

In return, Boston received Allen Webster, Ivan De Jesus, James Loney, Jerry Sands and Rubby De La Rosa, which again, on paper sounds lopsided. However, since the trade went down towards the end of the season, it’s too early to tell which team made out better. One thing’s for sure. It opened up a ton of money for Boston and could restrict the Dodgers from pursuing pricey free agents this off-season.

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