As a Cardinals fan, New York City, during the 2004 World Series, was a lonely place. If you haven't spent much time on the eastern seaboard, you might think New York is a Red Sox-fan free zone, but that's the opposite of true. There are Sox fans everywhere. They're real loud about it, too, because they all secretly feel guilty about having left New England to live among the bad guys.

Some of my best friends in 2004 were Red Sox fans, so before that Series began, we all agreed to keep our distance from each other. I wished them luck and waved goodbye. This was back before Twitter and Facebook, so we couldn't even virtually (and passive-aggressively) trash-talk each other. We just stayed out of contact.

When the Series was over, after they all washed the four days of partying out of their hair, we reconvened. It was a wise decision to stay away. There would have been fisticuffs, or at least an occasional lopsided scowl. One of those friends was Eric Gillin, co-founder (along with me, future Deadspin and Gawker editor A.J. Daulerio and current Syracuse journalism assistant professor Aileen Gallagher) of The Black Table, our old online journalism magazine. (Back when people did those.) Now he's the director of product for Epicurious, but he's still one of the biggest Red Sox fans I know.

Before the Pittsburgh NLDS with the Cardinals, I had a Know Your Enemy discussion with Deadspin writer Dom Cosentino, a Pirates fans. Before the Los Angeles NLCS, I fired questions off to Variety senior editor Jon Weisman. Now it's Gillin's turn. It's the Heat-esque détente before the battle. Neither of us will hesitate to take the other down.


1. So how greedy are you guys? You won your ALCS ... ISN'T THAT ENOUGH? How can you take away this title from the Cardinals, who so clearly deserve it? Who have suffered SO MUCH? 

Totally understand this question has comic implications, but as someone who regularly wears a Boston Red Sox cap around New York City -- thanks balding! -- I kinda understand the sideways glares I get from people now.

Those "long-suffering" Boston sports fans haven't really suffered in more than a decade. All four major sports teams have won. There is an entire generation of front-running, championship T-shirt owning Massholes who have the nerve to go thermonuclear when inexplicable NFL officiating costs the Pats a game against the Jets. Given that expectations were so low this year, winning the ALCS might seem to be enough on some level. But who roots for "enough?" I hope it's another red wedding for the Sox at the Card's expense.

2. So last year was a complete disaster, and here you are, back in the World Series. I know injuries, along with fighting, the manager and apparently chicken, were all problems last year. But what's so different about this year? Was last year the aberration? Was it just Valentine? Is this team more fun to root for just because they won more, or is there more than that?

Have you ever had a boss you hated? The kind of sociopath who would publicly call you out in front of co-workers, regularly praise underperforming cronies and ensure all of your mental energy was going into cataloguing your boss' every move and your subsequent reaction to that move. Who the hell wants to go to work in the morning and give 110 percent?

That's what life was like under Bobby V. I bet most of the players were so checked out -- hence the fried chicken and beer -- they were just waiting for the season to come to a merciful end to go to other teams, watch their manager get fired, go rehab their injuries, whatever. It's not all on Bobby V, but baseball players aren't very sophisticated humans. Simple math: Unhappy people don't do well at sports.

Here's what makes this team better than any Red Sox team of the last four or five years: They're fun to watch lose. It's hard to watch overpaid, overhyped, disgruntled millionaires with huge contracts lose. But these rejects? It's all gravy.

3. David Ortiz went from "Great All-Time Red Sox" team to "Red Sox Legend" this year, thanks to both his excellent season and his big speech after the Patriots Day bombing. He's also the only real link between this and the '04 team. I know Tom Brady is Tom Brady and all, but considering the importance of the Sox to this city, has he reached true icon status at that level? Are we gonna see a statue of him alongside Ted Williams and Carl Yastrzemski? 

Yes. This is his f--king city. But he was a legend before that speech. He cemented his status last year, when most Sox fans were in their "he's a Dominican guy who says he's 36, which means he's 39, and we're about to pay him how much again?" phase -- and his numbers have held up. I don't care if he's really 56 years old. He can still rake in clutch situations and he's the undisputed heart-and-soul of the team. Kinda puts the Manny Ramirez years in a new perspective, don't it?

4. I can't get a read on John Farrell. Do you guys like him? What kind of manager is he?

Not only do we like him, we love him. He's like the one who got away who came back. What if he never went to the Blue Jays? Would we have been subjected to the "fried chicken and beer" team? Would we have had that ill-advised one-season stand with Bobby V? And yet, he's unlike any manager the Red Sox have had. He's cerebral but rarely overthinks things. He bunts. He moves the runner over. He uses his bullpen when he's supposed to. He plays matchups. And he does all of this without resorting to Belichickian levels of silent dickishness to a Boston media that's just waiting to turn any long pause or change in tone into a major story.

The fact he hasn't stepped in sh-t yet is just remarkable, actually.

5. Who's the big folk hero on this team, the lovable role player guy? Or is it just collectively "beards?" Oh, and how did the beard thing start?

Can the entire team be a folk hero? Is that possible? These guys look like the Duck Dynasty and Smith Brothers Cough Drop beer league softball team. I went to Spring Training and saw them up close. Average and anonymous looking, besides all the tattoos. A little scruffy maybe. Looked decidedly not terrible. 

But then -- and I'm ashamed to admit this -- I didn't watch the team in April and May. I just scanned the box scores and kept up with some reading. Had trouble finding them on television since I live out of market and I don't make a huge effort to track down still photographs of baseball players. By the time I finally saw them on television, I couldn't tell the guys apart. Is this Mike Napoli or Jonny Gomes? Did they swap beards under the ring and come to bat twice in the same inning? It was amazing.

6. You and I have been friends for almost a decade-and-a-half now, so we knew well enough to get away from each other the last time our teams met in a World Series. (We'll do the same thing this week, though it's easier now that I don't live a subway ride away.) What do you remember most about 2004? The breakthrough, does it feel as strong now? Is it your best sports memory? Your family's?

My first memory of 2004 was watching Game 4 of the ALCS in a bar directly across the street from Grand Central Station. It was closing. We were the only Sox fans. The rest were Yankee-supporting staffers, putting chairs up onto tables and semi-aware of the game. They knew they were gonna win. They were ready to go home. Roberts stole. Mueller singled. The game tied up. The staffers stopped cleaning and started watching. Time slowed down. Papi hit the homer. We cheered. They got pissed. We ran like hell as they locked the doors behind us. 

I vaguely remember jumping around my living room when we finally swept the Cardinals, but really, my memory is talking to my dad after Game 3 and having the preparatory conversation. "It's not possible that we can finally win one of these, can we? You mean that's on the table?" As a breakthrough, the idea of winning that World Series holds up, but the best sports memory? It's really that comeback against the Yankees. I don't really remember that series against the Cardinals other than never feeling scared we would lose. It's all fait accompli at that point. We couldn't be beaten.

7. What frustrated me about the 2004 Series is the Cardinals basically ended up playing the Washington Generals that series: They were the supporting characters to the heroes. Do Sox fans have any thoughts about the Cardinals as a franchise? Do you hate us like everyone else seems to all of a sudden?

I doubt I could name a single player on the Cardinals right now. John Tudor? He's still pitching, right? 

Maybe I'm alone in this, but as an American League fan, I have never paid any attention to the National League on any level, ever. It's as if y'all are playing cricket or quiddich. I have enough trouble keeping track of the Red Sox farm system and the AL East, let alone the 42,000 people who will play professional baseball at some point this season. If I played fantasy baseball, I'd have a real, well-formed opinion on the Cardinals. I'd have no wife and no job, but I'd be able to name all of the Alou family members who played baseball, explain VORP and whatever other trigonometry passes as baseball knowledge these days.

So no, I don't hate the Cardinals. I tend to have a soft spot for any of the old-timey teams who have stayed in the same place for a long period of time, despite crumbling economies and huge eye tracts of the city looking like Snake Plisskin's jogging track. 

So yeah, I didn't hate Detroit either.

8. What would it mean to win this year? A legitimate breathtaking experience? Icing on the cake? A giddy surprise? That's to say: How, nine years after the 2004 rapture, does a Red Sox title feel today?

Yes, it would still be a legitimate breathtaking experience. It wouldn't be once-in-a-lifetime, unless you were a very, very sensitive 8-year-old, but you'd have to be some kinda asshole to give it a golf clap then promptly go online to buy some timely sports paraphernalia.

9. All right, let's get a series prediction out of you.

Will Leitch will obsessively watch baseball for the next 10 days and I will get a very polite congratulatory text message or a very exuberant text message that strikes a slightly conciliatory tone. 

My pick: polite congratulations over a digital platform after six games.

Twitter mailbag video Part One here.


Email me at, follow me @williamfleitch or just shout out your window real loud, I'll hear you. Point is, let's talk.