10 worst Boston Red Sox trades in team history

Babe Ruth Red Sox FF Portrait
Babe Ruth Red Sox FF Portrait / Transcendental Graphics/GettyImages
4 of 10

7) Worst Red Sox trade: Mike Boddicker for Curt Schilling and Brady Anderson

A lot of hindsight is needed for this trade to make the list. On July 29, 1988, pitcher Mike Boddicker came over in a trade with the Baltimore Orioles. The Red Sox would send them Brady Anderson and Curt Schilling. Wow!

Boddicker was a pretty good pitcher for the Red Sox with the biggest exception being his disastrous start in the ALCS against the Oakland Athletics. He allowed 6 earned runs, 3 home runs, and lasted just 2.2 innings. He was much better in his 1990 start, again versus Oakland, but came away as the loser again.

His regular season success of going 39-22 with a 3.49 ERA was definitely overshadowed by his October starts. When the Red Sox needed him most, Boddicker didn’t deliver.

Meanwhile, the Orioles ended up with a very good outfielder for more than a decade when they acquired Anderson. His greatest claim to fame was hitting 50 home runs out of nowhere in 1996. Even aside from that he was a base stealing threat in the early 1990s and a well-rounded hitter who reached base at a .364 clip for the Orioles.

Easily the most fascinating part of this trade was the presence of Schilling. No one knew at the time he’d become a Red Sox postseason hero. Traded by the Red Sox before actually playing a game for them, this is a case of wondering what those early Boston teams would have looked like if a different pitcher had been traded. Schilling didn’t start to have major league success as a starter until 1992 when he first joined the Philadelphia Phillies.

A seemingly necessary trade for Boston without the payoff, the history of this franchise would have looked much different with Anderson and Schilling on the roster throughout the 1990s.