Top Five Worst Red Sox Trades Ever Made

As we sit on the playoff sidelines—and contemplate a flurry of Winter trades—it might be instructive to look back at the five worst Red Sox trades ever. Keep in mind that Babe Ruth to the Yankees was not a trade, so that doesn't count. OK, here goes:

5. Dave 'Hendu' Henderson to the Giants for Randy Kutcher. Yikes! This 1987 trade—one year after Hendu's thrilling HR against the Angels—was a real loser. Henderson later went on to the A's and made it to the World Series three straight years (1988-1990). Kutcher batted .224 in three forgettable seasons with The Carmine Hose;

4. Sparky Lyle to the Yankees for Danny Cater and Mario Guerrero. This 1972 deal brought a 32-year old Cater to Boston. He had three "vanilla" seasons for the Red Sox. The 26-year old Lyle, meantime, had 35 saves in his first year in pinstripes—and eventually collected 141 in the Bronx. Bad trade, no biscuit!;

3. Fred Lynn to the Angels for Jim Dorsey, Joe Rudi and Frank Tanana. Lynn had four solid years in Anaheim and another three-plus in Baltimore. Dorsey, Rudi and Tanana all had short, non-impactful Red Sox careers;

2. Curt Schilling and Brady Anderson to the Orioles for Mike Boddicker. This 1988 deal did bring back a productive Boddicker (39-22 over two-plus seasons), but both Schilling and Anderson eventually became pretty big stars. Then again, we did get that Schilling guy back;

1. Jeff Bagwell for Larry Anderson. This horrendous 1990 deal sent a little-known minor league infielder to Houston for the one-year rental of an OK relief pitcher. Anderson was good (1.23 ERA in 15 games), but Bagwell became a force in Houston. He played 15 years there, hitting .297 with 449 HRs and 1529 RBIs. He was Rookie Of The Year in 1991, the 1994 NL MVP and a four-time All-Star. He may yet make the Hall of Fame. Worst. Sox. Trade. Ever.