Whenever he filled it out, he always picked Wisconsin to go on a deep run, including them winning the national championship last season.
"I had to pick them to win because I was committed by that point," Gasser said. "I love that kind of stuff, from fantasy football to the bracket, and I have to root for my teams."
Gasser hasn't done well on his brackets in recent years, mainly because his home-state team has not lived up to the expectations.
The success of the Wisconsin program under Ryan has been uncharted. The program has won five Big Ten championship in his 10 years, never finished lower than fourth in the conference, has the top winning percentage in the conference and the fourth best winning percentage at home over the last 10 seasons.
The month of March is a different story. Under Ryan, Wisconsin is just 35-21 (.675) in March, 22-17 (.564) in the post season and 12-9 (.632) in the NCAA Tournament. In the last five NCAA Tournament, Wisconsin hasn't made it out of the first weekend four times.
The fourth-seed Badgers (23-8) will try and reverse the trend this evening when it takes on No.13 Belmont (30-4) in the NCAA Tournament's second round in Tucson, Ariz.
For just the second time under Ryan, the Badgers enter the national tournament on losing streak, coming off an ugly 36-33 loss to Penn State last Friday in the Big Ten Tournament Quarterfinals. There were plenty of personal disasters to pick from – 29.4 percent shooting, 9.4 percent shooting, four bench points – but none more disappointing than the first 10 minutes, where Penn State outscored the Badgers 18-2.
"You get off to a slow start like that, that's it," said Gasser, as Wisconsin held the Nittany Lions to 18 points over the next 30 minutes but could never jump start its own offense. "We played good for 30 minutes, especially defensively, but we didn't play a good 40 minutes. That's what you have to do in the post season. If our season was done right now, the whole off season would be terrible for us.
"We know we get to play against after a performance like that."
It was also a challenging experience for Gasser, who has had personal highs this season like being the first freshman in conference history to record a triple-double and the first in UW history to hit a game-winning buzzer beater.
Gasser registered just one shot and zero points in 33 minutes, was pulled early from that game and questioned by Ryan about why he couldn't compete harder.
"He had to say that because we were getting out butts handed to us," Gasser said. "He had to do something to get us re-focused. They brought more energy and we can't let that happen. He said after one timeout that he wasn't going to say anything. You five go out there and talk to yourself and get focused."
Wisconsin has had some spectacular moments this season. The Badgers lead the NCAA in offensive efficiency (1.19 points per possession), free throw shooting (.824) and fewest turnovers per game (7.39), numbers that have given them wins over No.1 Ohio State, No.11 Purdue and Marquette.
Even with another 20-win season under their belts, there's no debating what a loss this weekend would mean.
"We have high expectations of ourselves so we would view it as a disappointment. We want to go to the Final Four and compete for a national championship. That's what great teams need to have their mindset as. Every game will be tough. If we don't bring it for 40 minutes, we will be done this weekend."
So with millions of people filling out there bracket this weekend, how far should people ink the Badgers? Although he has to retire from filling out a bracket for the next four seasons, Gasser didn't hesitate to give his insider's opinion.
"You should pick us not to lose," Gasser said. "We're not going to lose. Not a lot of picking us to go far, and that's OK with us. We're not going to go down easy. We're going to give it everything we've got."