Lou Gorman seemed like he was a good 4-5 years behind the times for much of his tenure as GM. Every winter was filled with "big" free agent signings and trades for guys that would have been far better pick-ups five years earlier.
I'm not sure if you ever read "Lords of the Realm" but any time Lou Gorman gets mentioned in that book, he gets hammered. GMs are always targeting him because he'll trade for anyone who was once pretty good and player agents are even worse. They always say that their client is really interested in the Sox, Gorman will splash the pot and the agent will use that to negotiate a deal with the player's original (or new) team. It was very rare that a really good free agent came to Boston (Kirby Puckett famously used the Sox in the early 90s). Reading it (and if you haven't read this book, you really should) made me feel bad for Gorman. He really wasn't a great GM, but he seemed like a nice enough guy who wanted to win for the Yawkey name. It was his naked pursuit of a World Series that got him this reputation.
David Cone and Billy Wagner were the 2 that came to mind after I started thinking about this. Then I started reading this thread and saw someone post Javy Lopez the catcher. Well, since I couldn't remember him on the Sox until reading it at that moment, I guess I need to add him to Cone and Wagner.
The one thing that I will never forgive TIto for is not letting Javy Lopez the pitcher throw to Javy Lopez the catcher. That's some bullshit right there.
Here's my list of the Weirdest Red Sox to Earn a World Series Ring. I'm defining "Weirdest" by a guy with a decent/noteworthy career outside of their time with the Sox, that was on the briefly, and was not a major acquisition or contributor to the team (so no Dave Roberts/Eric Gagne):
2004: Pedro Astascio - Made six unmemorable appearances in September/October. Ellis Burks should get a mention here, but I felt his presence was a little more noteworthy.
2007: Joel Pineiro - Tried to resurrect once-promising career in the bullpen, didn't go well, was traded mid-season. JC Romero is also a consideration.
2013: Matt Thornton - mid-season pickup to bolster the bullpen. Pitched decent but didn't make the postseason roster. Honorable mention to longtime noodle bats infielder John McDonald for his six games at the end of the season.
2018: Brandon Phillips is the obvious answer. Someone's going to mention Ian Kinsler, but he was a postseason contributor.
You can add
2004: Abe Alvarez, I think that he got in a game; maybe two.
2007: Royce Clayton, the long-time Giant was brought up at the end of the season and perhaps got a dozen innings*.
2013: Can't think of anyone off the top of my head. That was such a mismash of a team that if you told me that Buddy Biancalana somehow played for them, I'd probably believe you.
2018: I loved that Phillips played for this team and had his moment. As much as I loved the 04 team, I liked this one a speck more. I wish that Phillips hung around the team during the postseason like Clayton and Burks did.
* The thing that I really dislike about MLB killing the practice of expanding rosters to 40 after September 1 is that we're going to lose little things like this. For a guy like Clayton, he played 15+ seasons and I think that it's a nice capper to be on a World Series winning team, even if you don't get an at-bat or an inning in the field. It think it's a nice perk and humanizes these players. At the end of the day, it's difficult to connect with a superstar like David Ortiz or Dustin Pedroia or Josh Beckett. They're just so good at what they do, it's not even like they're the same species as mere mortals. But an aging Royce Clayton? You can see yourself as that dude, just hanging with the team in the best seat of the house. Pulling for you teammates, just happy to be there. It's a cool story and one that I bet he remembers.