While Frye, the Browns' 2005 third-round draft choice out of the University of Akron, was busy establishing himself as the Browns' quarterback of the future, Winslow was working his butt off just to have a future with the team that drafted him No. 1 in 2004.
But once the season ended, their worlds suddenly came together. Starting last January and carrying on throughout much of the off-season, Frye and Winslow were nearly inseparable.
Television cameras often caught them courtside at Cleveland Cavalier games. Out of the spotlight, they would spend long hours competing in video games or playing catch.
Frye and Winslow found they have much in common. Not only are both extremely talented football players, they also both possess an extreme desire to excel. "He's a competitor and that's what I am," Frye said during a break in mini-camp. "That's why we get along. He's a great guy. Everybody on the team likes him."
Maybe it's a good thing Frye didn't get to know Winslow when he first arrived in Cleveland in 2004.
Not everyone in Cleveland was convinced he was a "great guy." In fact, just the opposite might have been true.
He arrived in Cleveland with a chip on his shoulder and quickly turned off many people with an ego the size of his multi-million dollar signing bonus.
The fact he missed most of his rookie season after breaking his leg in Week Two against the Cowboys did little to rid him of his cockiness.
It wasn't until Winslow was seriously injured while performing motorcycle stunts following the '04 season that the light seemed to go on for the son of Pro Football Hall of Famer Kellen Winslow Sr.
A second straight season of sitting on the sideline seems to have humbled Winslow, who is finally healthy enough to once be playing football, albeit without pads and with very limited contact in the Browns' mini-camp.
Winslow says his inactivity has been a humbling experience. "It really has been," he said. "I've been working on being more humble. I've been given time to think, and time to get back."
He says it has been difficult being off the field. "Emotionally, there were a lot of long nights," he says. "I can't even really explain it. It was a hard time when my teammates were out there playing a game and I was at home with my leg up.
"But God put me in this place for a reason, because it wasn't my time yet. But now it's my time. I've had a lot of time to think about it, a lot of time to spend with my family, and it's good to be back."
There's still nothing to say that Winslow will ever get back physically to the same level he was at prior tot his broken leg and knee injury.
Head coach Romeo Crennel knows that better than anybody. "There is a lot of rust there," Crennel said, noting that Winslow has taken advantage of his down time to work on the mental aspect of the game.
"He has been around here for two years and even when he wasn't on the field, he was watching practice tape. He would get the call sheet and go down the sheet trying to understand what the calls were and what the routes are supposed to be.
"He was finding what his responsibility was and what the other players' responsibilities were. He was keeping up with the offense and keeping up with the meetings. It's not like he had forgotten football completely."
Winslow says he's not worried about the rustiness. "Not really," he said. "That's why we practice. I think I'll be OK. I feel about 90 percent. I've spent a lot of rigorous hours with (strength and conditioning coach (John) Lott and my teammates. There was a lot of pain and suffering I had to go through. But I'm almost back, and I'm happy to be back."
When informed Winslow said he was 90 percent, Crennel said, "Kellen knows his body better than I know his body. He still has a sleeve on the knee and I don't think it's 100 percent. It's not my body so if he says it's 90 percent, it's 90 percent.
"It still comes down to how he's going to do when he puts the pads on. He can still run. He didn't lose a tremendous amount of speed. I don't know if it is as good as it was when he came out of college, but he can still cut, make a catch and turn it up the field. It's not like he's dragging an anchor or anything."
Frye is even more glowing in his remarks. "Every day he amazes me with another great catch."
Yet to be seen is whether he still has the incredible quickness that, in the past, has made it very difficult for a linebacker to cover him. He has to show whether he can take a hit, whether he can still run the routes, catch the ball and block.
"He has to prove all of that to himself," Crennel said. "He wants to prove that he is the type of player that the Browns thought he would be when they drafted him. I think he really wants to do that and be the go-to guy. He wants to be the leader and he's competitive.
"Out here (in mini-camp), he still looks like he can run the routes, catch the ball and read the defenses. If he's able to go out there and show it in training camp, he'll have success on the field."
And when he is successful on the field while not acting like the cocky, spoiled player he was when he arrived in Cleveland, he'll have success in life as well.