Bronx Banter just published a list of their 25 least favorite Yankees from the last 20 years. That was inspired by a list of least favorite A's at Catfish Stew. I haven't followed the Sox closely for a full 20 years, so I alone can't possibly put together a full list of 25 for the Sox, but I figure we can try. I'll get started:
First off, the easy ones:
Byung Hyun Kim, Carl Everett, Shea Hillenbrand: duh.
Manny Alexander: somehow managed to be the only person in the Steroids Era to actually get caught. And yet he sucked. (Part of that whole "we need a third baseman, stat!" fiasco, also involving Wilton Veras, Ed Sprague, Chris Stynes...)
Izzy Alcantara: lazy fielder, batshit crazy in AAA (the video can be found here).
Now, the ones who are harder to hate - nothing obviously despicable about them, but whose tenure with the Sox made them hard to like...
Jeff Suppan: that Freddy Sanchez-Jeff Suppan trade in 2003 was really a Freddy Sanchez-Brandon Lyon trade. Suppan went 3-4 in August and September, with an ERA of 5.57, and was left off the postseason roster. Of course, then he bounces back to become an important part of the NL Champion St. Louis Cardinals the next year.
Mike Lansing: the best player ever to come out of Wyoming. Which is like saying Dick Cheney was the best Vice President to come out of Wyoming. Both are technically true, but...
Jose Offerman: I actually didn't hate him the way most Sox fans did (his 1999 season was actually quite good). But I'm pretty sure he makes this list anyway.
So those are the first 8 that come to mind...I know I'm missing a lot (others that might make the cut include John Wasdin, Patt Rapp, Brian Rose, John Burkett...), but I have to get to work. Anyone want to contribute in the comments?