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.

May 29, 2003: Red Sox trade Shea Hillenbrand to the Arizona Diamondbacks for Byung-Hyun Kim

(A little before the deadline, but still deserves a spot)

BK’s the closest thing we’ve seen to Eric Gagne in a Sox uniform. He came over in early June as a starter and went 2-1, although that’s pretty deceiving. In his two victories, the Sox scored a combined 36 runs (yes, 36) and he was generally awful. He went to the bullpen and was worse.

By the time the playoffs rolled around, he was an after thought. He only pitched 2/3 of an inning in the post-season but still walked a guy and gave up an earned run.

The one positive aspect of the BK years was the fun I had watching the slo-mo replays (over and over) of his face after giving up a home run, and coming up with different BK inner-monologues. All of which start with, "Ohhhhhhh!!"

As for Hillenbrand, he’s had his share of decent years since leaving Boston, but he’s also universally known as a douche and famously punched his manager in the face while playing for the Blue Jays. Good people, Shea.

July 22, 2003: Red Sox trade Brandon Lyon and Anastacio Martinez to the Pirates for Scott Sauerbeck and Mike Gonzalez

Back in the summer of ‘03, there was a ridiculous amount of hype surrounding Scott Sauerbeck. He was "supposedly" automatic against lefties, and with Mike Timlin dominating the eighth innings, the Pirates reliever was "supposedly" going to make the Sox bullpen untouchable.

Eh, not so much. It only took the Sox 16 2/3 innings to realize they wanted no part of Sauerbeck. In those 16-plus, he gave up 17 hits, walked 18 batters and hit another four—and at one point he also simultaneously robbed an old lady at gun point and kicked Johnny Pesky in the balls.

Somehow, Scotty found his way onto the playoff roster, and even though he only pitched a third of an inning, he still managed to make his presence known—he gave up a hit and walked a guy in the Sox 6-2 loss to the Yankees in Game 2 of the ALCS.

As for, Lyon and Martinez… they were involved in another questionable trade a soon after.

July 31, 2003: Red Sox trade Freddy Sanchez and Mike Gonzalez to the Pirates for Jeff Suppan, Brandon Lyon and Anastacio Martinez

Not content with the Sauerbeck debacle, a week and a half later the Sox decided to let the Pirates burn them again. They got Lyon and Martinez back, returned Gonzalez to the Pirates, and entered two new variables into the equation.

In Jeff Suppan, the Sox got a perennially average pitcher who would go 3-4 with a 5.50 ERA in 10 starts down the stretch. He didn’t even make the 2003 playoff roster.

Sanchez won a batting title for the Pirates in 2006 and has hit over .300 the last two seasons.

In Suppan’s defense though, he did his best to help the Sox win the World Series in 2004, even though he was then a member of the Cardinals.

July 31, 2007: Red Sox trade Kason Gabbard, David Murphy and Engle Beltre to the Rangers for Eric Gagne and cash

Have you seen David Murphy’s numbers this year? If not, check out the top 10 AL RBI Leaders. But truthfully, it wouldn’t matter if Murphy were batting .039 and Kason Gabbard was 1-17 with a 7.10 ERA. Gagne performed worse than anyone who’s ever worn the Sox uniform. In his two months in Boston, he almost single-handedly brought down the season.

Gagne would come into a game and you’d know 100% that he was going to blow it, and 95% of the time he did. He was the anti-Okie. No matter what the situation last year, you had full confidence that Okajma would wiggle his way out. With Gagne there was never a doubt that he would take the Sox lead and move his bowels on it.

Thankfully, in the end, Gagne will merely go down in Sox history as a punchline. Despite his efforts, they still won the title, and had the organization had the good mind to force him out of town last winter. But still, his ineptitude can’t be overlooked and won’t ever be forgotten.

Bonus Question: Who deserves their championship ring less: 2007 Eric Gagne or 2001 Terry Glenn?