ESPN Revisits ‘Worst’ MLB Trade Deadline Deal Red Sox Ever Made

No team is immune to a bad trade.

Even the smartest front office executives make poor decisions from time to time, and the pressure of the Major League Baseball trade deadline often serves as the backdrop for such organizational missteps.

ESPN’s David Schoenfield revisited the worst deadline deal each team has made in a piece published Thursday on ESPN.com. Some moves obviously are worse than others, sometimes setting back a franchise for several years, but the Red Sox’s worst deadline trade is enough to make Boston fans cringe.

Schoenfield pointed to Aug. 1990, when the Red Sox traded Jeff Bagwell to the Houston Astros for Larry Anderson.

Bagwell, of course, slugged 449 career home runs and carved out a Hall of Fame career in 15 seasons with Houston, while Anderson pitched just 22 innings across 15 relief appearances down the stretch for Boston in 1990.

Here’s more from Schoenfield, who also — cover your eyes, Red Sox fans — mentioned the 1988 trade that sent Curt Schilling packing:

The Red Sox actually have another deal that could be considered worse — we’ll get to that — but this is the classic prospect-for-rental deal that backfired in a big way: a future Hall of Famer for 22 innings of a setup guy. The one that was arguably worse? In 1988, the Red Sox traded Curt Schilling and Brady Anderson to the Orioles for Mike Boddicker — 115.3 of future WAR traded away. Boddicker did go 39-22 with the Red Sox and helped them win division titles in 1988 and 1990, so it wasn’t a complete disaster, however, and the memory of the Bagwell deal is stronger (in part because Schilling never did anything for Baltimore).

The Bagwell debacle doesn’t sting quite as much now that Boston has won four World Series titles since 2004, but there was a time — particularly during the slugger’s peak seasons — when it was criticized ad nauseam. Totally understandable.

It should be noted the Red Sox have made several savvy trade deadline moves over the years, too. None sharper than when the Red Sox acquired Jason Varitek and Derek Lowe from the Seattle Mariners in exchange for Heathcliff Slocumb on July 31, 1997 — which Schoenfield considers the worst trade deadline deal in Mariners history.