"Wesley lives in a nice neighborhood, he's well-provided for and he's very clean cut," Bucs' coach Richard Bailey said. "I think it's a credit to him that with that much freedom, he hasn't gotten into a whole lot of trouble. That's not to say he is a saint, or that he hasn't gotten into the kind of mischief 16-year-olds will from time to time.
"He has sort of figured out what is important. He is very mature for his age."
Born into a military family, Flagg's mother has been stationed in South Korea for the past year, while his father works a schedule that basically makes it impossible for him to see his sons except on weekends.
The family is close-knit and supportive mind you. Still, Flagg has had to rely heavily on his older brother, Brandon, 21, to help take care of him these last few years. And Flagg admits he's a "momma's boy" and misses her a great deal. However, he has also managed to maintain grades of A's and B's -- and was voted Homecoming King.
"It's not that hard," Flagg said. "My brother helps me out a lot. He's like another parent to me."
It's strictly school and football for Flagg right now, who said he fell in love with the Tar Heels when his Jack Britt team competed for a 4-A state championship at Kenan Stadium last year.
The Buccaneers fell 19-17 to Greenville Rose on Dec. 11 after having ousted No. 1-seed Mocksville Davie Co. in the semifinals a week before. But while Flagg would like to have left Chapel Hill that day with a victory, he knew from then on that he wanted to be a Tar Heel.
The playoff run also enabled Flagg to meet and establish friendships with future teammates Cooter Arnold and Logan Buchanan, both Davie Co. standouts.
"Cooter is tough to bring down," Flagg said. "Logan and I spend time together when we go to Carolina games." Flagg loves to play football, but he is not necessarily a football fan. He's one of the team's most vocal leaders and a real comedian on the field his coach attests.
"He has a really good sense of humor," Bailey said.
But Flagg grew up primarily in Japan where his mother was stationed, until the family returned to Fayetteville for the first time in six years, prior to Flagg's freshman year.
His older brother, Brandon, played football overseas. But, as Flagg explains, "You weren't allowed to play football in Japan until high school."
So when Flagg began playing, his coach was impressed with his athleticism, but considered him "raw."
"His I.Q. for football has really improved," Bailey said. "He gained about 15-20 pounds between his freshman and sophomore years. He looked like a changed kid. And he's just gotten smarter. He understands a lot more about football now than he used to."
Flagg said he plans to enroll at UNC during the summer semester.