The Poll Position MLB trade deadline extravaganza wraps up today with five of the most random deadline deals of the last 20 years.

July 29, 1988: Red Sox trade Curt Schilling, Brady Anderson and a set of sideburns to be named later to Baltimore for Mike Boddicker

Boddicker went 7-3 with a 2.43 ERA down the stretch for the Sox in 1988 and then racked up 32 over his next two seasons in Boston. The Sox won the pennant in two of the three years he was in the rotation.

Anderson had one great year and took enough steroids to kill a Monique.

As for Schill, I think it’s fair to say that the Sox eventually got more than they could have ever imagined from the big guy.

Eight years ago, you would’ve said Boston got the puny end of this trade wishbone, but all things considered, it turned out pretty well.

Today, with the MLB trade deadline looming, we take a look at the worst deadline trades in Sox history. Vote at the bottom and feel free to sound off in the comment section. Tomorrow, we’ll take a look at some of the stranger deadline deals in Sox history.

August 31, 1990: Red Sox trade Jeff Bagwell to the Astros for Larry Andersen

Andersen had a 1.23 ERA down the stretch for the Sox in 1990, as they took the AL East by two games over the Blue Jays. Or at least that’s how those who try to defend this trade see it. Bagwell’s three or four years away from a Cooperstown induction and he very well could be going in with a Sox hat on.

The one saving grace for the Sox is that they decided to give the Astros Bagwell instead of the prospect Houston really wanted: Scott Cooper.

Losing Bagwell was bad enough, you just don’t give up on a two-time All-Star like Cooper.

Note: When Cooper made that second "All-Star" appearance in 1994, he finished the year the year hitting .282 with 13 home runs and 53 RBI in 104 games. Bagwell won the 1994 MVP with a modest .368/39/116. And he did it in only 110 games.