Only after watching longtime friend Damian Lillard rocket up draft boards this month and get taken No. 6 by Portland on Thursday night did Cherry begin to believe he too could hear his name called this time next year.
Like Lillard, Cherry grew up in a rough part of Oakland. Like Lillard, Cherry received minimal interest from high-profile West Coast programs. Like Lillard, Cherry ultimately accepted a scholarship from a Big Sky program few of his peers even knew existed.
"That man right there, he's a role model for me," Cherry said. "As kids growing up, you always have a dream, but now that you see someone from Oakland who you played against since high school become a lottery pick, that makes it more realistic. You've seen the path he took, you played against him and you know what it takes to get to where he's going."
It will be difficult for Cherry to rise from lightly regarded recruit to small-conference star to lottery pick the way Lillard did, but the Montana guard is certainly on the NBA radar entering his senior season.
Cherry earned first-team all-Big Sky honors and the league's defensive player of the year award as a junior after averaging 15.8 points per game and leading Montana to a 25-7 record and a No. 13 seed in the NCAA tournament. He parlayed that into an invitation to last weekend's prestigious Deron Williams camp in Las Vegas, where he fared well against 16 of the top collegiate guards in the nation.
"Playing in the Big Sky, a lot of guys don't get the recognition, but on the heels of Damian's success that seems to be changing," Montana coach Wayne Tinkle said. "For Will to compete at that level and have the word spread, that's a great thing for him. He's going to be watched and scouted next year because of what he has been able to do."
Attention from NBA scouts is a startling phenomenon for Cherry because it wasn't long ago that he struggled to catch the eye of college coaches.
Despite scoring a team-high 19 points in McClymonds High's memorable upset of nationally ranked Dominguez in California's Division I state championship game his junior year, Cherry still had no scholarship offers the summer before his senior year. SMU, San Francisco and Santa Clara were the most interested in Cherry before Tinkle and his staff spotted him and encouraged him to take a visit to Montana.
To say Cherry was skeptical about the idea of leaving his big city comfort zone for small-town Montana would be a massive understatement. Cherry's coaches had to persuade him to accept the offer to even visit Missoula because he envisioned a scene right out of the Old West.
"Me being from the city, I stereotyped it," Cherry said. "I thought there were a bunch of cowboys and horses. I thought it would be the middle of nowhere. I didn't think they'd have a mall. I was like, 'I need a city around me to feel like I'm home.'"
What Cherry found instead was an environment more similar to McClymonds than he expected. While Montana's second largest city has not even one-sixth the population of Cherry's hometown, it supports University of Montana athletics the same way West Oakland embraces McClymonds' storied basketball program.
Cherry returned home from his visit and told his mom soon afterward that he wanted to commit to Montana. She encouraged him to sleep on the decision for a night, but the next morning they called Tinkle from the highway on the way to school to give him the good news.
Word of Cherry's decision inspired puzzled looks from most of his friends. Many of them asked him where Montana was.
"I was like, 'It's a state.' It's up north, by Idaho," Cherry said with a chuckle. "You won't believe how many times I got that question. Every time, I'd laugh and I'd look at them puzzled like, 'It's a state.' That was the most hilarious question I've ever been asked, and I got asked that over 50 times my senior year."
Cherry has made strides toward putting Montana on the basketball map, taking the Grizz to two NCAA tournaments in three years for the first time in school history. Along the way, he has benefited from leaving his comfort zone, overcoming early homesickness to become a more well-rounded person, a more vocal leader and an even more tireless worker.
Since Cherry and Lillard both had similar experiences leaving Oakland for Big Sky country, the two former high school opponents and AAU teammates forged an even stronger friendship in college. They texted or chatted as often as a few times a week, discussing life away from home or sharing scouting reports on conference opponents.
What Cherry has taken from Lillard's success story is the value of an insatiable work ethic.
Each day during the offseason, Lillard lifted weights, did an hour of game-speed drills and shot up to 400 3-pointers. The Weber State star returned better than ever from a broken foot suffered in Dec. 2010 as a result of his laser focus, even spending his 21st birthday shooting hoops and preaching the importance of education to kids at a local YMCA.
Cherry's dedication is just as legendary in Missoula as Lillard's is in Ogden.
He transformed his 3-point stroke from weakness to strength via hours in the gym, shooting 37.2 percent last season compared to 22.5 percent the previous year. This offseason, he hopes to keep improving his jump shot and become a more consistent playmaker off the dribble.
"My jump shot got a lot better, but I want to be to the point where it goes in every time I'm open," Cherry said. "My handles are good but I need them to be great. My playmaking ability is good but I need that to be great. Every element of my game, I need to take that to the next level."
Cherry planned to send a text or tweet congratulating Lillard as soon as the Weber State guard heard his name called Thursday night. And come this time next year, it could be Cherry whose phone is buzzing on draft night.