After Winding Journey, Will Cherry Follows Friendly Rival Damian Lillard to NBA

Cherry's deal with the Raptors is the culmination of his rise from Oakland through the Big Sky and NBA D-League.

Before Damian Lillard faced the likes of Chris Paul, Stephen Curry and Russell Westbrook each night, there was one point guard he couldn’t shake.

From the streets of Oakland to the mountains of Utah, Will Cherry stuck to Lillard like a thorn in his side -- the same way he guarded him and anyone else who crossed him on the court, for that matter.

Lillard averaged 22.4 points during a breakout senior season at Oakland High School; Cherry’s nearby McClymonds High team went 33-0 on its way to the state title. Lillard emerged as an under-the-radar star for the Weber State Wildcats; Cherry twice led the University of Montana past the Wildcats in the Big Sky conference title game.

“I respected him from the first time I ever played against him,” Lillard said of Cherry, whose games with the NBA D-League’s Canton Charge he tracked this past season. “He was just a dog. He played hard, he was aggressive -- fearless.”

Now, two and a half years after they last faced off, Cherry has trailed Lillard all the way to the NBA.

The news that the 6-foot pitbull of a point guard has signed with the Toronto Raptors comes three weeks after Lillard served as his former rival’s de facto promoter at the NBA Summer League in Las Vegas.

The Blazers star watched proudly as Cherry, a two-time Big Sky Defensive Player of the Year, hounded NBA hopefuls as the Cavaliers’ sixth man.

“He deserves to be on an NBA team,” Lillard told after Cherry finished with 21 points and a standing ovation from the crowd in his second game.

Their rivalry-turned-brotherhood is born out of a basic tenet of Oakland: The 510 takes care of its own. "When we're playing against each other, we do not like each other at all," said Orlando Watkins, who coached Lillard at Oakland High. "But once that final horn goes off ... we're actually a really close-knit city."

Eleven years ago, Watkins watched as Cherry exhibited all of the qualities of an Oakland point guard even while still in junior high: an unflappable court presence, a take-no-prisoners mentality and, most importantly, a burning desire to beat the player lined up across from him.

He arrived at the gym that day hoping he could convince Cherry to join Lillard at Oakland High. Instead their paths ran parallel: Lillard's eventual success at Weber State led Montana coaches to pursue Cherry, Watkins said.

By the September of 2012, Cherry was poised to become the next sleeper out of the Big Sky when he broke his foot during a pick-up game. Montana coaches sat him down to discuss the option of red-shirting his senior season.

"Coach, I can play," he told head coach Wayne Tinkle.

Tinkle estimated that Cherry played at 60 percent from the time he returned in December until March, when he led the Grizzlies to their third NCAA tournament appearance in four years to the detriment of his pro prospects.

“He was so passionate about his teammates that were there at the time that he didn't want to let any of them down,” said Tinkle, who has since moved on to Oregon State.

Still not fully recovered after graduation, Cherry played just 12 minutes for the Pelicans at the 2013 Summer League and waited for offers from European teams that never came. "This injury set me back a little bit," he told Watkins, "but when I get an opportunity, I'm gonna take it and run with it."

"That's what people from Oakland do," Watkins said. That opportunity came in February, when the Charge sold him on taking the NBA D-League route to his ultimate goal. The partnership proved beneficial for both sides.

Canton reached the playoffs for the third consecutive year, while Cherry averaged 11.6 points and 4.5 assists in 18 games.

He soaked up knowledge -- particularly on the nuances of the NBA’s staple play, the pick-and-roll -- from a staff led by first-year head coach Steve Hetzel, who in June was hired by the Hornets as an assistant. His invitation to join the Charge’s parent club in Las Vegas served as a stamp of approval of his diligent work.

“Last year at the Summer League, everything was moving so fast. Fresh out of college, you don’t know what to expect,” Cherry said during a Summer League in which he averaged 12.8 points on 52% shooting in 25.2 minutes per game. “In those two months, with my coaches from the Canton Charge, everything slowed down for me. I give them all the credit for teaching me, going over film every day.”

At 23, Cherry heads to Toronto as the player everyone from Oakland to Montana envisioned he could become: a dynamic floor general, whose quickness, court vision and improved jump shot have built him into a pick-and-roll weapon; an ultra-competitive scrapper with an insatiable work ethic, who entered Montana as a wiry teenager and left looking “like an NFL defensive back,” Tinkle said; and still, above all, the defensive dog Lillard met all those years ago.

“I was most proud of how he just stayed Will,” Lillard said. “He was always Will Cherry, whether he was new to a team or things weren't going well.”