Brian Baumgartner Is The Buffalo Bills Of ‘The Office’ Fantasy Football League

If there’s one thing Brian Baumgartner has mastered over 20 years of fantasy football with The Office cast and crew, it’s getting to the championship game. The problem? He hasn't quite figured out how to win the championship game.

"I’ve made our Super Bowl more than anyone else — never won," Baumgartner told me on Wednesday. "Always a bridesmaid. Always the Buffalo Bills of The Office fantasy football league."

As the Buffalo Bills of the OutKick fantasy league, I feel his pain. I just can't get over that second or third place hump.

Brian Baumgartner has been in a fantasy football league with his castmates from "The Office" for more than 20 years.

(Joe Vulpis)

The Office league is serious business, though. This is a two-decade-old, trash-talk-heavy competition that started on the Dunder Mifflin set with a yellow legal pad passed from desk to desk. If an actor was filming or busy? The draft just sat there until they had time to make a pick. Weeks later, maybe someone would finally draft a kicker.

"There was no minute-and-a-half time limit. It was like, whenever you can get to it," Brian recalled. "And then, if you were sitting there, and you were taking a long time, you'd get yelled at, of course, by Rainn."

He was referring to Rainn Wilson, who played Dwight Schrute on the show. And honestly, policing the slow drafters sounds like something Dwight would do.

Watch the whole interview with Brian Baumgartner here:

Eventually, the league went online, and things got a little more efficient.

"For a few years, after hours, we’d bring some Sam Adams Octoberfest into Dunder Mifflin and sit at the computers — which were active on the set of The Office — and we would draft there," Brian said. "I don't know if NBC would like this story. Just occurred to me maybe they wouldn't appreciate that. But that's what we did."

These days, the crew — including Brian, Rainn, John Krasinski and other longtime Office staffers — are scattered all over the country. Their commissioner, Stephen Saux, somehow wrangles everyone into one draft time. Saux was a longtime stand-in on the show and appeared in a couple of episodes as well.

"We're probably drafting at, like, 4:30 a.m. Eastern on a Sunday or something. I don't know when we're all going to be able to figure it out," Brian said. "But we all love it. The trash talking began last night when the draft order was sent out, and it'll continue 'til late December."

Octoberfest, Chili Season & That One Scene He’ll Never Escape

Brian teamed up with Sam Adams this year to promote the "Fall Legends Commissioner’s Kit" — a gift pack celebrating the hardest-working person in every league. It comes with a commissioner vest, a coin for settling disputes, a koozie and Brian’s favorite: a gavel. 

"Gavels are just inherently fun," he said.

For me, seeing Octoberfest tap handles pop up in bars is the official signal that we've finally made it to football season. Brian agreed.

"You know the draft is right around the corner," he told me. "Then it’s chili season."

And yes — I went there. After all, he was the one who brought up chili, knowing full well that he probably hasn’t gone a single day without someone referencing the most famous cold open in Office history: Kevin Malone’s tragic chili spill.

"You never hear that joke about Kevin's famous chili, do you?" I asked.

"Never," Brian laughed. "But everyone who says it thinks they’re the first one."

At least I had the self-awareness to know I hadn't come up with anything original.

Brian Baumgartner's Hot Takes: Trash Talk, Team Loyalty & Draft Day Food

When I asked about the league’s top trash talker, Brian gave the nod to Rainn Wilson. He also commended Rainn's resiliency.

"He’s not always a great drafter, but he never gives up," Brian said. "He’ll start 1-4, make trades, work the waiver wire, and somehow scrape into the playoffs."

Let that be a lesson to those of you who lose a few games and then quit setting your lineups altogether — ruining the experience for everyone. That's my fantasy football pet peeve.

Brian's pet peeve, though? Cheering for your fantasy team over your real-life favorite team.

"There is almost nothing that I dislike more than being in a sports bar establishment… and having someone rooting for their fantasy team. Oh, it makes me crazy," Brian said. "I understand it's controversial. I understand. But like, you know, someone gets tackled, and you start hearing some guy or gal gripe about their fantasy team. That does legitimately bother me. So for me, it is always about team. Always about team."

If Brian could pick an all-time dream fantasy lineup (regardless of era), he'd go with Barry Sanders, Derrick Henry, Ja’Marr Chase, Calvin Johnson and his "old pal" Aaron Rodgers.

Brian Baumgartner and Aaron Rodgers became friends while sitting at a blackjack table in 2008.

(Photo by Michael Buckner/Getty Images for Entertainment Weekly)

When it comes to pairing beer with draft day food, he’s skipping the cliché buffalo wings, chips and dip — at least for now. What's on Brian's menu?

"Thai chicken skewers," he said without hesitation. A little random, but there are no rules here. "I'm sticking with that. I'll wait 'til October for chili."

And before you say anything… yes, he'll do his best not to spill it.