Red Sox 25-man roster from the past quarter century

On Friday, Baseball Prospectus’ Russell Carleton issued a challenge to anyone who wanted to take part.

The directions were pretty straight forward. Pick one player from one team’s roster in each of the last 25 years. Fill out an entire roster without repeating players. In other words, you can’t use 1999 Pedro Martinez followed by 2000 Pedro Martinez. It’s one or the other.

I saw this tweet Friday night and immediately decided to dive into making the Red Sox version of this roster. It was a task I thought would take just a few minutes, but actually took longer than I’d care to admit. There were a lot of moving parts and a lot of tough decisions to make. Here is what I ended up with.

I’m pretty happy with what I ended up with, and am confident it’s an extremely strong roster. It took me a little while to figure out how I wanted to tackle this. At first, I figured I’d go year-by-year, but that would’ve been too hard to keep track of positions. Instead, I started with individual seasons I knew I wanted to include. I knew Mookie Betts would be my representative from last season, and I knew 2011 Jacoby Ellsbury would be my center fielder.

After that, I picked out some players who had multiple great seasons here. I knew David Ortiz was going to be my DH, I just wasn’t sure what year I wanted to use. This actually filled out the largest chunk of my roster, and included others like Dustin Pedroia, Pedro Martinez, Roger Clemens, Nomar Garciaparra, Manny Ramirez and Mo Vaughn.

Finally, it was as simple as matching the blank years with the blank positions. At this point, I mostly had to fill out my rotation, bullpen and bench. The lineup and front of the rotation were mostly set. In the end, I got a good representation of the last 25 years of Red Sox history. I will admit, however, that my memories of pre-1999 Red Sox are hazy, so I just went strictly by numbers there.

Anyways, what would you change? What did I mess up? Yell at me in the comments.