Data from Traded: Inside the Most Lopsided Trades in Baseball History

Are Trade Deadline Deals Really Worth It?

As the National League celebrates its first All-Star Game victory since 1996, general managers are gearing up for those oh-so-important trade deadline deals. But how important are they? Doug Decatur, author of Traded: Inside the Most Lopsided Trades in Baseball History , has shown that teams that trade away young prospects for proven veterans in an attempt to win a World Series now rarely come out on top.

Even in 2008 when the Brewers and Dodgers made two of the largest impact deadline deals of all-time, acquiring C. C. Sabathia and Manny Ramirez respectively, neither club reached the World Series.

Historically speaking, 14 of the top 50 most lopsided trades of the twentieth century were deadline deals (trades made between the original trading deadline of June 15 to August 31, the deadline for playoff eligibility.)

1. July 29, 1988:
Red Sox traded Curt Schilling, Brady Anderson to Orioles for Mike Boddicker

2. August 30, 1990:
Red Sox traded Jeff Bagwell to Astros for Larry Anderson

3. August 28, 1983:
Braves traded Brett Butler to the Indians for Len Barker

4. July 27, 1989:
Rangers traded Sammy Sosa to White Sox for Harold Baines

5. July 23, 1910:
Athletics traded Shoeless Joe Jackson to Indians for Bris Lord

6. July 29, 1996:
Mets traded Jeff Kent to Indians for Carlos Baerga

7. June 15, 1964:
Cubs traded Lou Brock to Cardinals for Ernie Broglio

8. June 28, 1995:
Astros traded Luis Gonzalez to Cubs for Rick Wilkins

9. August 31, 1980:
Expos traded Tony Phillips to the Padres for Willie Montanez

10. July 31, 1989:
Expos traded Randy Johnson to the Mariners for Mark Langston

11. July 20, 1916:
Giants traded Edd Roush to the Reds for Buck Herzog

12. August 12, 1987:
Tigers traded John Smoltz to the Braves for Doyle Alexander

13. July 31, 1997:
Mariners traded Derek Lowe, Jason Varitek to the Red Sox for Heathcliff Slocumb

14. June 15, 1975:
Athletics traded Chet Lemon to the White Sox for Stan Bahnsen

These 14 trades became lopsided because the main prospect traded in the deal became a star.

Was it worth it for the team trading the future star? No. Thirteen of the 14 teams giving up the prospect failed to win a pennant. The only club who produced a pennant was the 1910 Philadelphia Athletics and they had to cough up a young Shoeless Joe Jackson to do so. Ironically, “one” is the same number of pennants won in the same year as the trade by the teams giving up the veteran players for a prospect. That one team was the 1964 Cardinals, who not only got the prospect in the deal, future Hall of Famer Lou Brock, but they also managed to win a World Championship in the same year.

Trades are an important weapon in a GM’s armory, but deadline deals are not a successful way to win a pennant in the same season. The teams which are successful at the trading deadline are not the ones looking to make the playoffs, but the ones acquiring the final piece to a World Championship puzzle, such as the Phillies acquisition of Joe Blanton in 2008.

Information provided by Doug Decatur, the author of Traded .