Archbishop Wood's practice field did not have lights, but Webb, Pitts, and a few other teammates would stay out there for hours in the dark until then-Wood head coach Steve Devlin kicked them off the field so he could get home. Webb introduced Pitts to the value of after-practice reps, so putting in extra time was a no brainer.
"Football is something that I love to do," Pitts said. "I don't get bored with it. I don't drag on to practice. Any time I can get some extra work in, and it'll help me — I'm with it."
The two grew close off the field, too. So much so that Pitts describes Webb as a "big brother." Webb calls Pitts his "little big brother" because of Pitts' five-inch height advantage and jokingly calls him "moose" because he says Pitts resembles the animal. Since high school, Webb has been Pitts' go-to person for advice about anything from football to money management to relationships.
Webb and Pitts led Archbishop Wood to the 2016 5A state title. Pitts led the team with 28 receptions that season and caught a touchdown in the 37-10 win over now Dallas Cowboys linebacker Micah Parsons and Harrisburg High School.
That summer, Pitts and his father traveled up and down the East Coast playing in almost every football camp and tournament they could find. Until then, Kelly Pitts knew his son was good. After seeing him at a football camp in Florida, he realized that Kyle Pitts was special.
"He never ran like that before. His routes were different. Everything was different about him," Kelly Pitts said. "Whoever was supposed to be the top cover guy, top linebacker or the top kid there couldn't touch him."
Kyle Pitts grew two inches to his current 6-foot-6 by the time his senior football season came around. The hype around him significantly increased after his impressive summer, and power five college coaches began filling up the stands at Archbishop Wood games to see the tight end up close.
"It was all over then. He looked like a man amongst boys. Folks did not want to see Kyle like that on the field," Kelly Pitts said. "When I saw the recruiters, I was like, 'Well, damn! What is this about?'"
Archbishop Wood went on to win their second straight state championship that season and Pitts had a game for the ages, catching a touchdown pass while securing two interceptions as a defensive end. The game is one that Devlin still thinks about today and said defined Pitts as a player.
Outside of what he did on the football field, Devlin was most impressed by how humble and great a teammate Pitts was despite the national attention during his senior season.
"He took school seriously, he took training seriously, he took football seriously and, and he was a great role model for a lot of people," Devlin said. "I think to this day, he still tries to outwork everybody, and that's what makes him special."