It was an evolution forged by opponents' wild elbows on the blacktop courts at Ash Park every summer and fine-tuned in gymnasiums across the county with the Red Raiders' varsity team each winter.
Tooles played his final game as a senior for the University of Connecticut in 2004 on the floor of the Alamodome in San Antonio. He walked off the court an NCAA champion.
Then basketball - a daily part of his life, for most of his life - ended.
"I used to play every day to take your heart," Tooles said. "Now I still work out every day, but I only play basketball when summertime comes."
Now Tooles is back in the limelight, making a name for himself as a rapper. Performing as "Toolez," he has delivered a 22-minute set of tracks from his CD "Reloaded" before 7,000 fans and opened for Kanye West and Ludacris at Connecticut's annual spring concert.
The performance instantly introduced Shamon Tooles, the rapper, to a new group of hip-hop fans.
"People see you playing basketball all of your life, and first I had to just convince people (I could rap)," Tooles said.
The Connecticut concert was not the Coatesville native's debut. By that time, he already had convinced many people in his hometown and his college teammates of his musical talent.
But Tooles said it did mark the moment when hip-hop stopped taking a back seat to basketball.
Rap had been his "summer hustle," especially in college when writing rhymes, making recordings and later selling his CDs out of the trunk of his car always came second to practice, off-season workouts and summer league games, he said during an interview earlier this month.
Today, Tooles, 27, records his albums with a Downingtown-based independent record label called 50/50 L.G. Entertainment, which is owned by another Coatesville resident and high school classmate Mondre "DJ $Dre Money$" Boggs. Tooles is vice president of the label.
Tooles still makes his home in the city, where he spent some time living in the Parkway and Oak Street housing projects as a child.
"I learned a lot before I was supposed to because of those two places," he said. "The core of who I am comes from Coatesville. I've learned so much in college, but growing up in Coatesville prepared me for it."
His father, Damon White, a club DJ in Philadelphia, helped shape his musical tastes, he said. His dad also got his son interested in reading album credits, explained to him what a producer did and taught him about the metaphors in song lyrics.
Tooles remembers when he and his cousin wrote out the lyrics to Notorious B.I.G. tracks on paper and dissected their meanings.
Tooles was 6 foot 5 by the time he was a senior in high school. In his final season, Coatesville's boys basketball team won the District I title and advanced to the Pennsylvania Interscholastic Athletic Association Class AAAA before losing to Chester High School and standout guard Jameer Nelson in the semifinal game. Playing center, Tooles averaged 16 points and 11 rebounds per game and was named to the all-District I team.
At Connecticut, coach Jim Calhoun played Tooles sparingly. Although he did start a few games in his career, he mostly was used as a defensive specialist. After basketball was done, Tooles returned to the university for a fifth year and finished his degree in political science.
His latest album is "I Am Legend," and he performed songs from the album in concert on Friday in Baltimore as part of the bill for the E&R Smoke Tour, which includes rapper T.I., whose sixth album, released last summer, debuted at No. 1 on the album charts.
"This is not my first go-around. I'm not the guy who just started rapping yesterday," Tooles said when asked what he thought it would be like to be part of the show. "Things are different for me."
One difference between Tooles and other independent label rap artists is that Tooles' cell phone is programed with the numbers of current NBA players like Ben Gordon of the Chicago Bulls, Emeka Okafor of the Charlotte Bobcats and Charlie Villanueva of the Milwaukee Bucks.
And of course he has the phone number of another Coatesville and Connecticut alum, Richard "Rip" Hamilton of the Detroit Pistons.
The two are friends, Tooles said, and Hamilton influenced his decision to go to Connecticut, where Hamilton and his teammates won their own NCAA championship in 1999.
There has always been a friendly rivalry between the 1999 and 2004 Huskies teams, Tooles said.
"We got one up on them," Tooles said. "We got NBA players. They got NBA players. But no one from that team ever rapped at the spring concert."
Then again, Hamilton does have the Rip City Celebration in Coatesville every year. Tooles admitted he has some catching up to do before he reaches Hamilton's heroic status in the city.
With the direction he sees his music career going, he said he can close the gap.
"Maybe me and Rip can have a day together."
Join the discussion at the Coatesville Roundtable, http://www3.allaroundphilly.com/blogs/dailylocal/coatesville/blog.html.
To contact staff writer R. Jonathan Tuleya, send an e-mail to jtuleya@dailylocal.com.
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