A 'Cutty' Above: Former Bears QB Cutler Teams With LITH Cornhole Pro

LAKE IN THE HILLS, IL — Jay Rubin will be the first to admit that his first run-in with former Chicago Bears quarterback Jay Cutler wasn’t on the friendliest terms.

The two met at a bar in Wrigleyville during Cutler’s rookie season in Chicago and to hear Rubin tell it, the encounter didn’t leave him with the best impression of Cutler. But now, years later, Rubin — a Lake In the Hills resident who has played professionally on the American Cornhole League circuit for the past four years — has paired up with Cutler in a different environment.

And this weekend, the two will be shooting for a championship at the ACL’s World Championships in South Carolina after winning a qualifying event last month in Chicago. For Rubin, teaming up with a former NFL player who performed under mixed reviews during his time with the Bears, has given him a different perspective on Cutler, who remains as competitive as ever.

“Who he is now as a person versus who he was as a player and athlete at the time are two completely different people,” Rubin told Patch.

“We’re both fathers, we’re both the same age and so things were pretty loose and relaxed and we just wanted to have some fun with it. We just wanted to do the best we can and hopefully put on a good show.”

The Rubin and Cutler combination advanced out of the Chicago qualifier after Cutler delivered with a timely toss that found its mark in a clutch situation. Needing a bullseye throw to tie the match, Cutler came through by airmailing his final throw into the hole before he and Rubin pulled out the win at an event that paired ACL pros with celebrities.

With his fellow competitors reminding him what was at stake, Cutler took his time before someone from the crowd reminded him that the moment was similar to other pressure moments he had been in before.

Cutler, who was not available for an interview for this story per an ACL spokesman, paused his throwing motion and responded to the nearby fan.

“It’s not (the same),” Cutler said. “I wish I was playing football. This is much harder.”

In one fluid motion, Cutler released a shot that hit close to the target and slid the bag into the hole just as Rubin had instructed.

Cutler reacted to his match-tying bullseye by raising his arms in celebration with a finger extended on each hand. For Rubin, getting the chance to spend time off-stage with Cutler allowed the two to establish a connection that eased some of the pressure of competing together in front of a live audience.

Cutler told Rubin that he had played some cornhole on a casual basis before last month’s qualifier. While Cutler was sent bags and a board to practice on a month before the Chicago event, Rubin was impressed with the touch Cutler was able to put on some of his throws once the two got into the actual competition.

His background as a star quarterback at Vanderbilt and then in the NFL certainly helped, Rubin said. Rubin said he tried to assist Cutler with some of the finer points of cornhole, like developing a good slide shot or air-mailing technique that can help build up points in competitive cornhole settings like the one the two find themselves in this weekend at the world championships.

“Him being a quarterback and understanding accuracy or a touch pass or a fade pattern in the back of the end zone (helped),” Rubin said. “It’s about finding that sweet spot in the middle of the board where he could hit it every time.”

Rubin added: “He’s obviously played in pressure under the lights …. But he listened to what I said and took his time. He seemed pretty adaptable and was willing to listen to take any advice I could give him.”

Other competitors at the Chicago qualifier also noticed Cutler’s competitive spirit, especially when he found his team in need of a clutch scoring chance with the match on the line.

WGN sports anchor and former NFL running back Jarrett Payton — the son of Bears legendary running back and Hall of Famer Walter Payton watched as Cutler soaked in a different competitive environment than the one he was on during his playing career.

Yet, while Cutler is still relatively new to competitive cornhole, especially an event in which he is playing against teams that include ACL professionals, Payton said the former Bears quarterback’s ability to maintain his cool in the Chicago event was unmistakable. Payton characterized Cutler as someone who has always had a chip on his shoulder and that was no different when it came to proving himself on this stage.

“He came to play,” Payton told Patch this week. “He came to win that thing, man. It wasn’t like he was there to just show up. He was coming to win.”

Payton added: “Once that’s in you, it’s in you, and it’s hard to turn it off …when you’re an athlete, something has to tick inside you of you just a little bit different than everybody else.”

Payton said that while all former pro athletes maintain a healthy competitive spirit after their playing careers are over, Cutler’s desire to win hasn’t dwindled much since his NFL career ended in 2017 after he spent the final year with the Miami Dolphins after being released by the Bears.

Heading into this weekend’s world championships, Rubin expects the competition level to be much higher than it was in Chicago. While most of the professional cornhole players will cancel each other out with their performances, it may come down to amateurs like Cutler to make the difference when it matters most.

The winner of this weekend’s event will have $10,000 donated to charity.

“In that situation, with (some amateurs) having more experience, those guys are probably going to have a leg up,” Rubin said. “But we’re really going to have to capitalize on every opportunity we have to score points.”