Curt Schilling and Brady Anderson for Mike Boddicker – 1988
The Red Sox were looking for an established veteran starter with postseason experience and ended up getting exactly that from Mike Boddicker. The deal worked out pretty well in the short term, but this is a classic example of why pushing your chips in to win now can backfire in the long run.
Boddicker went 7-3 with a 2.63 ERA down the stretch for the Red Sox to help get them to the postseason, but was lit up for 6 runs in a loss to Oakland in the ALCS. He followed that with two more solid seasons, going a combined 32-19 with a 3.66 ERA to wrap up his tenure in Boston.
Not bad for a trade deadline acquisition. What the Red Sox got out of Boddicker isn’t what makes this a regrettable deal, it’s what they gave up for him. It may have taken a few years to realize what they lost, but in retrospect the Red Sox ended up giving up a very valuable prospect that they would have been better off keeping.
I’m of course referring to Brady Anderson, who years later blasted 50 home runs and finished in the top-10 in MVP voting. The Red Sox sure could have used that one brilliant season from Anderson in 1996, but instead they had to watch it happen for the division rival Baltimore Orioles.
Oh, they also gave up Curt Schilling, who went on to have a Hall of Fame career.
Schilling was a late bloomer who didn’t break out until years later when he had already moved on from Baltimore, but the Red Sox could have reaped the benefits of some of his best seasons if they had patiently waited for him to develop instead of dealing him for a quick fix. Boddicker did a fine job in Boston, but would you rather have him for a few good years or potentially have Schilling for his entire career?
Boston rectified this mistake by bringing Schilling back in 2004 and he ended up winning a pair of World Series rings in a Red Sox uniform. It worked out in the end, but you have to wonder how many more rings this team would have won if they had Schilling in the rotation through his prime years instead of only the tail end of his career.