MLB Trade Deadline: Top 25 midseason deals of all-time

23. Orioles acquire Curt Schilling and Brady Anderson, July 29, 1988

Remember the Wild Card didn’t exist in baseball until 1994. When the Boston Red Sox won 15 out of 16 games heading into a July 29 doubleheader against the Milwaukee Brewers shortly before 1988 trade deadline, but still trailing in the division standings, the club made an aggressive move to add pitching depth to the starting rotation.

The trade, which included two prospects for Mike Boddiker, worked out in the short-term. Boddicker, a 30-year-old right-hander was 7-3 with a 2.63 ERA in 15 games (14 starts) for the Red Sox, and helped Boston win the division. He was lit up in his only start in the ALCS against the Oakland A’s but the trade accomplished its goal of winning the division. Plus, Boddicker pitched two more seasons for the club, with his last start also coming against the A’s in the 1990 ALCS.

But it’s interesting to think what might have been if the Red Sox hadn’t made the trade. After all, the two prospects in the deal were Curt Schilling and Brady Anderson.

Schilling pitched three seasons for the Orioles, and was traded to Houston and then Philadelphia before establishing himself as one of the best pitchers in baseball. In a 20-year MLB career (which included four seasons and one bloody sock with the Red Sox), he posted a 3.46 ERA and amassed 3,116 strikeouts, putting him in the discussion for the Hall of Fame.

Anderson, who played 41 games for the Red Sox in 1988, spent 14 years in Baltimore. He was a three-time All-Star, and put together one of the most surprising offensive seasons in history, hitting 50 home runs in 1996 despite never connecting for more than 21 in any previous season (and no more than 24 in any future season).