"To see the Cubs and Wildcats turn it around in the same year, it's such a treat," said Sherry, 45, who earned a bachelor's degree from Northwestern in 1993 and a master's in 1995. "You're almost waiting for the other shoe to drop."
Instead, the Wildcats are expected to be slipping on dancing shoes. And fans of both teams are pinching themselves. Their luck, it seems, has finally turned.
"When you're going through it, you don't get the perspective of the big picture," said Jay Sharman, who ran the popular NU sports blog laketheposts.com from 2007 to 2015. "You're so neurotic about your team and thinking the world is set against you. It's crazy. I'm 43 years old and I'm nervous as hell (about the tournament)."
Sharman said he went to every home basketball game as a Northwestern student and had season tickets until - interestingly enough - this season. A New England native, he became a transplant Cubs fan as an NU student, taking the L to buy bleacher seats for Friday afternoon games. He attended playoff games this year and sensed history was being made.
He sends a weekly email to 50 people, including such NU alumni as ESPN commentator Michael Wilbon and "Late Night" host Seth Meyers. He and some of his friends plan to attend the first NCAA Tournament game, wherever it may be. But they feel like they're tournament newbies.
"It's so new to us," Sharman said. "We're like, 'What do you do? How do you book hotel rooms?' "
Sharman said he asked his wife to keep the calendar clear in March.
"I declined business meetings," he said. "I'm going. We don't care. Orlando, Sacramento or Tulsa, we're going."
Helen Chen, a Cubs fan since childhood, graduated from Northwestern in 1997 with a bachelor's of music and added a master's of music in 1999. She convinced her friends to delay a group trip to Cuba from October to November in case the Cubs made the World Series. She attended Game 7 in Cleveland.
"It was very surreal," she said. "I was pretty numb watching that last out."
And now she is rearranging life again to follow the Wildcats on their tournament journey.
"We know we have to be there," she said of herself and two friends who have season tickets and watch televised road games together.
Chen, 43, painted her nails red and blue during the baseball playoffs. Since basketball season began, they've been various shades of purple. Co-workers at the insurance firm where she works wear purple on her birthday.
"It's starting to be a borderline obsession," she said with a laugh.
NU fans are finally coming to grips that their basketball team could follow in the footsteps of the Cubs. Nobody is predicting a championship for the Wildcats; one step at a time. Fans of both teams compare Northwestern to the 1984 Cubs. Making the tournament is a historic, giant jump.
Sherry said he almost passed out at last week's game against Michigan, which the Wildcats won on a wild last-second shot that seemed to wrap up a tournament bid.
"People said Northwestern needs to make a statement to get into the tournament. This was like the Gettysburg Address," Sherry said. "It's a wonderful sports year for fans of both teams."