Not may receivers at Wynn's size -- he weighed less than 150 pounds when he got to Indiana -- can play in the Big Ten. Many people told Wynn he couldn't.
But he's proven those people wrong over his first three years in Bloomington. And while things certainly haven't come easy, they weren't quite as hard for Wynn last season as they had previously been.
With talented guys around him, including Cody Latimer and Kofi Hughes, Wynn flew under the radar. He played in the slot and got more one-on-one opportunities because of the guys playing on the outside.
Those opportunities led to 633 receiving yards on 46 receptions and a team-high 11 touchdowns. Wynn emerged as one of the top receivers in the Big Ten.
Things are different now. Latimer is now a member of the Denver Broncos, and Hughes will try to make a team in training camp. Both guys are gone, leaving Wynn as the lone returning receiver who made significant contributions last season.
"I definitely miss those guys," Wynn said Monday at Big Ten Media Day. "They taught me so many things. You couldn't double any of us. I miss those guys just joking around, just playing around. Now it's, I'm the leader, I'm the senior. There's not many receivers on our team that have played in big games, so now I can't really laugh around like I want to. I'm focused on being a vocal leader now."
Wynn, the goofy, charismatic wide receiver not laughing as much? That seems hard to believe.
"It's true in some aspects," quarterback Nate Sudfeld said, smiling. "He's definitely still an energy guy, joking around. But he has definitely taken his leadership role more seriously and brought guys along. He understands, for him to get more catches, he has to help other guys get open. He's been a great leader and is working really hard."
Indiana brings in a talented class of receivers that features Dominique Booth, but the group as a whole is untested and unproven. If the offense is to avoid taking a step backward, it will be key for Wynn to help the young guys grow, and grow quickly.
"I almost forget Dominique is a freshman because he's been here so long," Wynn said of Booth, who has been with IU since the spring. "He'll see a lot of playing time this year."
For Wynn, leading and mentoring a new crop of receivers will undoubtedly be a challenge, but he's also in the process of re-learning to play the outside receiver spot. He's been in the slot for the last three years.
"I'm still having a little trouble, but I'm working on it," Wynn said. "I'm getting better at it, of course, but there's still a lot of work I need to do."
Sudfeld admitted it hasn't been easy for Wynn to learn the new position, but he has confidence in his senior receiver to be ready when the season rolls around.
"He's put a lot on himself to learn to be an outside guy," Sudfeld said. "There's definitely been a learning curve for him. He's getting out of his comfort zone a little bit, but I really thing he's gonna do fine. I feel like he can play multiple positions and not miss a beat."