Regardless, the two defensive linemen verbally committed to North Carolina minutes apart during the same unofficial visit on July 21.
"We have talked about going to the same school before, but committing that weekend really wasn't a topic," Drennon said. "We were just going down for the visit."
While both Drennon and Webb were highly recruited, their recruitments followed different paths. In April, Webb verbally committed to Penn State and was 100-percent firm until the circumstances forced him to look around. While Webb was set with his school, Drennon was visiting campuses attempting to find a home.
"I wanted to make sure that when I made my decision that I made the right decision so I wouldn't have to go through the whole de-committing process," Drennon said.
Both Webb's and Drennon's paths crossed in June when Webb decided to visit UNC while in the area visiting family.
"That visit definitely put them on the map for me," Drennon said. "I always liked North Carolina, but when Greg told me he was going down to take a visit, I thought ‘Why not.' And actually it came to something totally more than that."
Shortly thereafter, Drennon narrowed his focus to Kentucky, Notre Dame, UNC, and West Virginia.
"With those four, I had visited and there was a high chance for me to play early," Drennon said. "Two of the schools, West Virginia and UNC, there was plenty of room on their depth chart at my position because of graduation or they were starting a new position. With Kentucky, it's an SEC school so I'd be playing against top competition."
According to Drennon, UNC is recruiting him for the Bandit position in its 4-2-5 defense. Since the previous regime didn't utilize that position, UNC's roster is void of adequate depth at Bandit.
Primarily, Drennon is a pass rushing specialist for Timber Creek. But he does have plenty of experience dropping into coverage.
"He's not a guy that is playing man coverage on a No. 2 receiver," Timber Creek head coach Rob Hinson said. "But if he's playing in the flats, hook/curl he definitely can do it. We work those drills pretty much every day and we do run a 4-2, so we're familiar with what [Larry Fedora] did at Southern Miss and there's a lot of similarities."
Regardless of where Drennon plays, Hinson believes the sky is the limit.
"He's a guy that is nowhere near reaching his potential," Hinson said. "At the end of last basketball season, he was 214 pounds. He's only 240 now. He didn't do AAU [basketball], so this last year was his first year where he was 100-percent football. Basketball may have slowed down his development initially. At this point, he's a football player through and through. Not only has he put on size, but he's starting to watch football more. He just has an unlimited ceiling, because he could [become] 260 pounds and be just as explosive."
Drennon's parents accompanied him on every recruiting trip, except for the June visit to UNC. Thus, he decided to return to UNC with his parents, as well as Webb and his family.
"I wanted to take my parents back up there to see what they thought about it," Drennon said.
During the visit, Webb and Drennon had separate, back-to-back, individual meetings with Larry Fedora. Webb went first and, unbeknownst to Drennon, had verbally committed to UNC.
"There was a feeling in the air like [Webb] was going to commit," Drennon said. "And then when I went into the room, Coach Larry Fedora, he said ‘We just got one of your guys and we just want to know are you ready to make that commitment too?' My parents didn't even know [that I was about to commit], but it just came out. I felt like ‘Why wait any longer, this is where I want to be. I felt at home."
Additionally, Drennon would receive his parents' seal of approval and had already established a bond with UNC's players, whom he had spent some time with prior to his commitment.
"The players were a big help, because they felt like they were my brothers already," Drennon said. "I had only been with them two or three hours, but I felt at home with them."
In hindsight, UNC had everything Drennon was looking for in a school.
"I feel like once I had gotten down to Carolina – I had gone down there twice – I felt like it was the right place for me," Drennon said. "My best friend is going down with me, it's a program on the rise, and the position that they're going to have me playing I'll be the first person recruited specifically for that position. I feel like getting on the field as a freshman would be easy – that was one of my big things. Academics at UNC are great – it's a very prestigious school, so a degree from there will get you any job. I just felt like everything about North Carolina was great."
Throughout the recruiting process, Drennon kept in regular contact with Dave Duggan, his primary recruiter, and Deke Adams, UNC's defensive line coach.
"Coach Duggan is a great guy," Drennon said. "I talk to him a lot over Facebook. I don't really get to call him that much, because our camp times don't really matchup. But he's a great guy, he's high-spirited – so is Coach Adams. Coach Adams and I can talk about football for just hours and hours."
Drennon expects both he and Webb will make regular appearances in Kenan Stadium this fall.
"Six hours away, that's nothing," Drennon said. "We might be down there every weekend. They might become sick of us."