A consensus around the room revealed that Crosby, Eric Fehr and Olli Maatta are usually the most competitive guys when it comes to their league, which has 12 teams. Some guys work alone; others pair up to be co-general managers.
"Olli's probably one of the most active guys on fantasy football, quietly," Crosby said. "He's always looking to make deals because he loves to work the phone and try and get some deals going."
Did that surprise them, that a kid who grew up in Finland was so into the sport?
"A little bit, but he knows football," Crosby said. "He watches a lot. He knows all the players. He's always open for business, Olli."
Maatta says that playing fantasy football is what got him into actual football, and he's now obsessed with both.
"Definitely when I get into stuff like that, I take it serious," he smiled. "I do. But at the same time, I enjoy it and I have fun with it and I think all the guys are doing the same."
While Crosby and Fehr both singled Maatta out as the most competitive, he pointed the finger right back at them.
"Sid is, while Fehrsy thinks he's running an actual football team," Maatta laughed. Which is kind of true - more on that below.
But all jokes aside, Maatta said that being in this league together is a fantastic bonding experience for the group.
"I think it's absolutely one of the best things we do as a team, just to see guys compete in something else other than hockey," Maatta said. "It's pretty cool to see when you can bring the competitive side of each other out."
And if there's one thing the guys can set that competitiveness aside for, it's to give Phil Kessel a hard time.
"There's not really that many rivalries. We just like seeing guys that can't win not win, and Phil's one of those guys," Fehr joked. "We like to see the same teams lose every week."
Crosby is the one to beat this season, as he and co-GM Kevin Porter finished in first place last year.
"We had to swing a couple big deals," Crosby said. "We picked up D'Angelo Williams, that was a good pickup off the waiver wire. Then we also traded Derek Carr for Doug Martin, that was a good one. And we picked up Doug Baldwin off of waivers, I don't know how he was on the waiver wire. Those guys came up big for us."
Unfortunately, Fehr had a much less successful year - joining Jeff Zatkoff's team as co-GM after it was already on a slide after a tough trade with Crosby and finishing at the bottom of the standings.
"I got really behind the eight ball last year coming in and starting on an 0-3 team that had just sold the farm to Sid," Fehr said. "I had a really rough year last year. This was my chance to redeem myself and that's what I'm trying to do. Every day, every trade, every pickup, every waiver claim is to try and redeem myself from last year."
Fehr also doing everything he can to make the league better, joking that he had a few issues with how it was ran last season, calling it a 'free for all.'
"If a guy got injured during a game, you could go pick up a running back right then and there," he explained. "So the guys that were single and staying at home watching football were watching it go down. They'd pick guys up and boom, they'd load up their team. The married guys with kids were out at the parks, we'd come home and all the guys were gone. So that was another disadvantage we had last year."
So this year, Fehr proposed they have a waiver process so every NHLer has a chance at every NFLer.
"Olli would pick up and drop eight guys in a day," Fehr said. "So I said, 'We've got to have a waiver process. You pick a guy up; you go to the bottom of the line.' That way everyone gets a chance, and you have to actually think about what you're doing. That has helped this year, I think. It's really increased the parity of the league."
And while Maatta understands that change was for the good of the league, it was still an adjustment for him.
"I did not like it," Maatta laughed of the rule changes. "I think it might be fair, but I did not like it because I was usually the first guy. I'd be sitting on my phone watching football and seeing the waiver wire, whoever was available. But it evens things out and I think it's good."
Another change, said Fehr, was rewarding whoever wins first place each week.
"Some people would be too scared to make moves if they had bye weeks," Fehr said. "They would just sit on their team and lose on purpose. You get incentive to win every week and if you finish first in the league in the regular season, then you get rewarded also. Because that's hard to do and then you don't burn weeks.
"Sid burnt a week a couple weeks ago because he had a couple people on a bye and he didn't want to change his team, so he just lost on purpose. That screws up everybody else because whoever he's playing against gets a free ride. So we're trying to really encourage people to make moves and I think our league is growing. It's better for it."
Despite all of his successful campaigning to improve the league, Fehr is the least-liked GM in the room right now, according to sources.
"Nobody likes the guys at the top," Fehr shrugged. "What are you going to do?"
And while Crosby acknowledged Fehr is off to a strong start, he cautioned against getting ahead of themselves.
"We're not even halfway through the season yet, and he finished in last last year," Crosby laughed. "I think there's still a lot to be done as far as who's top in the league. But he's had a good start."
Fehr says the animosity stems from a deal he recently made involving one of the NFL's hottest players that sent shockwaves through their league.
"I made a fair trade with another individual," Fehr said. "We both agreed upon it. Guys don't like that not everybody got a chance at this player, that I snuck in and took him before everybody knew he was available. So guys are mad at me. I feel like that's just their fault for being bad GMs and not having their ear to the ground. You need to know what's going on. Everybody has a price. Every player is available for a price."
"HE'S JUST GOT TO LOOK IN THE MIRROR"
If there's one thing Crosby and Fehr can agree on, it's that Kessel's team is struggling the most.
"We bug Phil because he's the least active GM out there, but he should be the most active," Fehr said. "His team is struggling; he's got a lot of injuries. He needs to pick up the phone and try to make a deal but he overvalues his players way too much. He thinks the world of them, which is great, but he needs to have a bit of a reality of the situation he's in or he's going to miss the playoffs."
Crosby was a little bit harsher with his assessment of Kessel.
"Phil's team is terrible," Crosby laughed. "Like, it's awful."
I asked Crosby if Kessel perhaps got stuck with a bad draft position.
"I don't know. I mean, he's just got to look in the mirror, I think," Crosby joked. "His team has not been good and it's been like that. I think he co-GM'ed last year with somebody and didn't do well. So I don't know. He's got some work to do."
Maatta's team with Justin Schultz is struggling as well, but he's not too worried yet.
"We had a rough start, me and Schultzy," Maatta said. "But we're getting better. I think we're a playoff team. We don't worry about the regular season. We just want to make the playoffs."
Crosby added that Marc-Andre Fleury's team is one to watch.
"Flower gets a lot of help from a member of our medical staff, Curtis Bell," Crosby said. "So I don't know how much say Flower has. I'd say C. Bell is the GM and Flower more kind of okays everything. But C. Bell does a lot of the work."
While he's feeling pretty confident right now, Fehr said it's too early to say who could win it all.
"Right now, it could be anybody's game because injuries in fantasy football are crazy," he said. "So there's a couple teams that are doing well right now, but a couple star players go down and that changes things. So I'm not going to predict any winners right now, but there's some good teams out there."