Why is the Ivy League’s best player taking a year off from playing basketball?

All his life, it was simple: Caden Pierce played basketball. He played basketball a lot.

Sure, there were other sports, other ways to sweat and scrape his knees. But from a very young age, there was nothing like finding small ways to win at five-on-five. A well-timed cut. A bounce pass through traffic, thumbs turned to the floor. Perfectionists keep satisfaction at a distance. But those things, the minutiae, how they would tip the scoreboard little by little, could get him pretty close.

Eventually, Pierce grew, kept hooping, grew some more, kept hooping. A whole existence formed around the next game. So in August, a week before starting his senior year at Princeton, he had trouble trying to label the absence of that structure.

“Sitting out? Gap year? Redshirting?” said Pierce, a Glenbard West graduate, taking a breath during dinner at a restaurant in his hometown. “I don’t have a name for it. I just say I’m not playing.”

Still, that didn’t feel as if it explained enough. A young guy walked by with his family, nodding. Pierce nodded back, the language of 20-some-year-old dudes who sort of know each other.

“I’m preserving my eligibility?” he offered. “I don’t know, man. It’s complicated.”

*** *** ***

Complicated is a popular word in modern college sports. Pierce’s version is this: He is sitting out/taking a gap year/redshirting/not playing/preserving his eligibility after three standout seasons at Princeton, where he was named Ivy League rookie of the year as a freshman, then conference player of the year as a sophomore.

The reason, at least the biggest one, is so he can finish his degree in economics, spending this year at Princeton as a nonathlete, a regular old student, before transferring to a bigger program for his final college season.

And the reasons for that, at least the two biggest, are so he can showcase himself against tougher competition and make the big money that Ivy League schools don’t offer.

College athletes have earned over-the-table money off their name, image and likeness (NIL) since July 2021. This summer, that evolved to schools paying them directly for the first time, giving five-, six- and seven-figure salaries to top players in football and basketball, which had previously been exclusively brokered by donor groups.

But none of that has happened in the Ivy League. None of those donor groups, known as NIL collectives. No revenue sharing between schools and athletes. The league doesn’t even permit athletic scholarships (and Pierce’s family pays his full tuition).

So Pierce, a 6-foot-7, positionless wing, officially enters the transfer portal Wednesday. The expectation is most top schools will call.

Money is important but not the sole factor in his decision. After starting at Princeton with four other freshmen, he’s the last remaining player in his class. Two of his favorite assistant coaches are gone, too, having left the program in the spring. Pierce also played through torn ligaments in his ankle last year.

At 21, with the hope of hooping as long as he can, it feels like a good time to reset, sharpen his offensive skills, get his legs back to 100% and impress pro scouts on the other side. But if Princeton paid its players as power conference programs do, or if it did anything to shrink the financial gap, would he be doing this?

“I can’t say for sure, but it’s 1,000% a harder decision,” Pierce said. “It wasn’t an easy choice, but you can see why I would do that. There is lots of money out there, higher-level basketball, a chance to prove myself. Yeah, I love Princeton and everything it has given me. But it just felt like the scale has long been leaning toward this being the right move.

“College sports have changed so much.”

*** *** ***

The Pierces are no strangers to the transfer portal. They were actually pioneers, going back to the spring of 2019.

Justin, the oldest of three boys, had worked like crazy, bulking up his course load, to graduate from William & Mary in three years. He was already a 1,000-point scorer. His coach was on the way out.

And if he transferred, he figured, the next school would pay for his graduate degree, plus he could see how he stacked up against better competition.

The rules were much different then. Because only grad students could switch programs without sitting out a season, experienced, plug-and-play veterans — much like Caden is now — had gone from a market inefficiency to essential for success. Justin was among the top-ranked grad transfers, and he had the option to enter the portal with a “no contact” tag. But, really, how many schools would it be?

A dozen? Two dozen max?

“In the first 48 hours, I’m not even joking, I would take a 15-minute phone call, hang up and have seven or eight voicemails,” Justin recalled. “It was never-ending. My girlfriend didn’t see me for three days.”

After the coaches talked to Justin, they would call his father, Greg, who was a college athlete, married a college athlete, then raised three college athletes with his wife, Stephanie. Alec, the middle brother, went to Cincinnati and is now a wide receiver for the Indianapolis Colts. But Justin, seven years older than Caden, was first through the door, the family’s introduction to the very top of college sports. In about a month, Justin narrowed his list to North Carolina, Notre Dame and Michigan, ultimately joining the Tar Heels. Greg still has a voicemail from Hall of Fame coach Roy Williams saved.

Drawing a line from Justin to Caden, what’s similar is that teams all over the country are interested.

What’s different is … well, everything else.

“They’ll go through Caden’s agent,” said Justin, laughing from Seattle, where he works in finance for Nintendo. After college, he played four years overseas, including stops in Finland, Germany and Japan. He continues to play on FIBA’s three-on-three world tour. “There was no such thing as agents in college then. It was me and our dad, taking on the world.”

*** *** ***

Five springs later, after the 2023-24 season, the trend of mass player movement reached the Ivy League. Point guard Malik Mack, the league’s rookie of the year that season, left Harvard for Georgetown. Chisom Okpara, Mack’s Harvard teammate, jumped to Stanford. Tyler Perkins, another freshman guard, went from Penn to Villanova. Yale lost star big man Danny Wolf to Michigan.

NIL — in this case, shorthand for earning money elsewhere — was the driving factor. Princeton, though, retained its core, most notably keeping Pierce and point guard Xaivian Lee. The year before, when Pierce was a freshman starter, the Tigers made the Sweet 16 of the NCAA tournament. And while they stepped back in 2023-24, losing in the Ivy League tournament semifinals, Lee chose to return after testing the NBA draft waters. That was enough for Pierce, who had decided to leave only if Lee did.

“For me, if I was going to transfer, it was going to be after that sophomore year, when I had won player of the year and wasn’t so close to my degree,” Pierce said. “But once Xaivian came back, we had another shot with a great group. Other teams weren’t reaching out to me directly, but they passed things along through a high school coach, an AAU coach, whatever. You start to hear what you could make somewhere else and it’s like: ‘Huh. Really?’ It gets harder and harder to ignore.”

A year later, then, this past spring, Lee transferred to Florida. Forward Jack Scott left the team and wound up at Duke. They were supposed to be Pierce’s senior-year roommates. With them gone, he would have been the last senior on the roster, playing without his best friends.

That’s when he really started to consider sitting out. There were cons, of course. He wondered about rust, especially without access to Princeton’s gym and weight room. By skipping a season, he also will be a year older when he eventually jumps to the pros, whether that’s the NBA, the G League or a team overseas. And maybe more than anything, he worried about how he would feel once the season started, when the team took the court and he couldn’t get closer than the stands. The basketball team was — is — his main social circle. There was a lot to lose.

Pierce decided there was even more to gain. He had talked it through with his parents, brothers and agency, Priority Sports. They all agreed, but it was Pierce’s choice to make. Just before the Fourth of July, he called Mitch Henderson, Princeton’s coach, and told him he wouldn’t be playing. He then called each of his teammates, one by one, then the entire staff. A few days later, he posted a letter to X and Instagram, titled “Thank You, Princeton Men’s Basketball …”

“What I’m learning as I continue to grow is that the only constant in life is change,” Pierce wrote, and while he vowed not to read the comments, it was impossible not to peek. As expected, a few posters saw the move as a shameless money grab, a sign of everything that’s wrong with college sports. But most of the strangers understood, some even floating that this could become a trend in the Ivy League.

“He has the chance to get his grad degree paid for and make connections with a whole new alumni base,” Justin said. “And then we’re talking about life-changing money, too. The reality, and I’ve told Caden this, is that overseas, the G League, whatever it is, if you don’t make the NBA, you won’t make this kind of money again for the foreseeable future. Sure, you can go up the totem pole in corporate America, but it would be decades before you’re touching this kind of money ever again.

“For a 22-year-old to have a nest egg like that, it’s invaluable. It will all open a lot of doors.”

*** *** ***

When Pierce returned to school in August, he and his mom went to a women’s soccer game. Pierce’s girlfriend is on the team, and after a weird summer, after fretting so much about the biggest call of his life, watching her play, being back at Princeton, was close to relief. He was just a bit nervous about seeing his old teammates.

When he did, though, the tension passed with some light ribbing. Then a football player suggested he try out for tight end.

“I could see him take a big, deep breath,” Stephanie said. “It was like ripping a Band-Aid off.”

Last week, Pierce left an afternoon class — The Roman Empire: 44 B.C. to 337 A.D. — and split from a few of his former teammates. They were headed to the gym. He was walking back to his apartment. He lifts at the campus rec center, setting an extra early alarm to beat the morning rush. He recently returned from China, where he competed with the U.S. under-23 three-on-three team. Soon, he’ll start working with a skills trainer in the area, someone connected to his agency. He will sink into new routines, even if they never feel normal.

And as of Wednesday, coaches can officially reach out to his agent, talk numbers, plant their flag in the Caden Pierce Sweepstakes. Pierce likened it to a high school recruiting process, taking place in the fall and winter, not a hurried stretch next spring. But there are a lot of unknowns, none more tricky than how most rosters will flip again after the season.

Pierce could visit a school, vibe with the staff, fall in love with the program and campus, then watch them recruit two similar players in April. Sure, he’s versatile. And, yes, his experience and skill set should make him a fit on almost any team. There just has to be some art to this, doesn’t there? Some dos, some don’ts? Should he have all the possible data before picking a school? Or should he jump when an offer feels right, even if it comes in October? What about November? January?

“The unknown of it is exciting,” Pierce said. “At this point, I can’t wait.”