LOUISVILLE, Ky. — Charlie Greenleaf ’63 grew up in Indiana, playing basketball and following the sport closely. “Ever since I was a little kid,” he said, “I’ve gone to tournaments — the high school tournament in Indiana and now the college tournaments.” 

He traveled to see the Princeton men play in the NCAA Tournament nine times before this year, dating back to the 1980s. But last week’s first and second rounds in Sacramento, California, seemed too far away to arrange travel on short notice. 

Then the 15th-seeded Tigers gave him a second chance, upsetting Arizona and Missouri to reach the Sweet 16 for the first time since 1967. Greenleaf and his wife, Maureen, jumped at the opportunity. On Wednesday, they started the 600-mile drive from northern Virginia to Louisville, Kentucky, where they’ll watch the Tigers face Creighton on Friday night (9 p.m. ET on TBS).

Alumni from around the country are converging on Kentucky for what promises to be a sea of orange (or at least a healthy-sized lake) at Louisville’s 22,000-seat KFC Yum! Center. According to Brendan Van Ackeren, an associate director of athletics, Princeton sold out its allotment of 1,000 tickets in a few hours Sunday, and many Tiger fans who missed out on that chance have bought tickets through other sellers. For those staying closer to home, at least 30 Princeton regional alumni associations have arranged watch parties, from New York City to Taiwan.

Jim Waltman ’86, a longtime fan who, as a kid, followed the Tigers to Madison Square Garden for the 1975 NIT championship, donned a festive trilby with an orange-and-black checkerboard pattern as he and his wife, Alicia, boarded their connecting flight to Louisville (drawing a hearty “Go Tigers!” from an uncle of one Princeton player). “There were a lot of over-the-top Reunions costumes last week [in Sacramento],” Waltman said. “I’m sure there will be this week, too.”

Read more PAW stories about Princeton in March Madness

The turnout from the Class of 1998 promises to be particularly strong, with friends and former teammates coming to support head coach Mitch Henderson ’98. The class will celebrate its 25th reunion in May and has been having a string of de facto mini-reunions in the basketball postseason. 

“We’re going to see a lot of each other this year,” said Darren Hite ’98, a friend and former teammate of Henderson who attended the games in Sacramento and is flying to Louisville from San Francisco. As of Wednesday, he was expecting to see others coming from as far away as England and Peru.

Brian Douglas ’98, one of Henderson’s former roommates, followed the Tigers to Indianapolis in 1996, taking a spring break road trip in an aging Buick Regal. Douglas and fellow traveler Doyl Burkett ’98 were rewarded with a close-up look at one of Princeton’s most memorable wins, a 43-41 first-round upset of UCLA in Pete Carril’s last season as head coach.

Two decades later, Douglas brought his family to see the Tigers play at the 2017 NCAA Tournament (a two-point loss to Notre Dame in Buffalo, New York), and for this year’s Sweet 16, they’ll be driving in from the Chicago area. 

Princeton is the first Ivy League men’s team to advance this far in the tournament since Cornell in 2010. “Watching the evolution of Ivy League athletes over the past 25 years, these men and women are really talented athletes,” Douglas said. “It was a matter of time before this was going to happen.” 

For Greenleaf, the most memorable NCAA Tournament trip may have been in 1998, when Princeton played the first two rounds in Hartford, Connecticut. The Tigers, who cracked the top 10 of the AP national rankings that year, dispatched UNLV in the first round, setting up a second-round game against Michigan State.

“It was more interesting for me because at the time, I was a vice president of Michigan State,” said Greenleaf.

But true to his alma mater, he wore Princeton gear (“subdued,” he insists) while sitting in a section of Michigan State administrators and trustees — and invited some Princeton friends to join him. “They were banished after the half,” he said.

Princeton lost the game, 63-56, ending its spectacular season. That’s the one downside to following your favorite school in March Madness, Greenleaf said: “Usually, it winds up in a defeat sooner or later.”

But rallying around a team and reconnecting with friends creates memories, win or lose, alumni said. 

“You know how nutty the alumni base is in general,” Douglas said. “Give us something extra to cheer about and … it’s lively, it’s exciting.”