“It’s Like Working Inside of the Vatican”: How a Former Red Sox Intern Ended Up Making a Documentary About Their 2004 World Series Run

What was your job in the front office? What did they have you doing up there that you were so bad at?

Oh, I was terrible. One of my first jobs was I worked a switchboard and I would relay the calls. Every once in a while I’d get a prank call from somebody in baseball operations trying to get down to the clubhouse to see if I would do it. And more often than not I would be like, “Yeah, sure, why not?” They’d be like, “No, no, no. Wait.” They’d break character and be like, “You can’t do that.” Oh. So then I worked the mail room for a little bit.

I remember this the team went down to Florida to play the Marlins. I was supposed to send the scouting reports down there, and I forgot to. They got swept, and we missed the playoffs by three games. And I was like, Ooh. So, the last job I had as an intern there—which doesn’t sound real, but it’s 100% true—they sent me out to measure the width of every seat in the stadium. They were switching out seats, so I did that for the last two, three weeks I was there. Then, yeah, I went down to the clubhouse, thank goodness.

Was it weird making a documentary almost about your own life? I know you weren’t there in ‘04, but reliving this through the eye of the camera must have been weird.

It was a little weird, but the weirdness was overtaken by the comfort of the surroundings. A lot of these guys, we would interview down in the spring training facility. And nobody ever leaves their job at Fenway Park. Like I said, it’d be giving up a job at the Vatican. So, the ability to just walk around and feel comfortable in the setting—because walking into a clubhouse and there’s a bunch of pro athletes around, there’s certain rules and they’re unwritten and you don’t know what they are. To be able to walk around and at least have a general acknowledgement like, “Oh yeah. No. We know who he is. He’s fine,” was very helpful. They’ve seen me around, but they’d be like, “The last time I really worked with you, you were literally washing my underwear.” But it helped in terms of just the casualness and the candidness of the interview.

Was it difficult for you to square your opinions on someone like Grady Little, for instance, with trying to make an objective documentary about him? Because I’m sure in ’03, you probably wanted to run him out of town too. [In 2003, the Red Sox lost a Game 7 heartbreaker to the Yankees when Little famously left Pedro Martínez on the mound far longer than most fans wanted him to.] When you get him in the interview, did you find him to be more of a sympathetic figure?

I was at Game 7 in 2003. It was the first regular season or postseason game outside Fenway Park I had ever been to. My dad chose that day and that game to bring us to. So when I sat down with Grady, I was—he won 95 games as a manager back-to-back years. [In 2002, the Red Sox won 93 games. In 2003, they did indeed win 95.] I did think that his imprint on 2004 is never mentioned, but he’s the guy who—Kevin Millar’s going to Japan! He’s out of baseball. David Ortiz is being released. He’s out of baseball. Bill Mueller, who won the batting title, he’s coming back from a horrific knee injury. Grady’s the guy who allowed them, cultivated them, gave them the confidence to become the icons of Red Sox history they are now. And yeah, did he make a mistake in 2003? I asked every single player what they would’ve done, and every single player said, “I would’ve left Pedro in.”