From his high school days through college at Syracuse, Flynn has relished the role of the scoring point guard who has the freedom to attack the basket and create his own shot at a moment's notice.
It worked for him in high school, where he led Niagara Falls, N.Y., to the public school state title and became a McDonald's All-American.
It worked for him at Syracuse, where his fearless play lifted the Orange to the Big East tournament title game and made him the No. 6 overall selection in the 2009 NBA draft.
In Minnesota, Flynn is being asked to play the position in an entirely different manner. Rookie head coach Kurt Rambis calls for the point guard to be an organizer and distributor in his flow offense. Flynn's opportunities to freelance and play off of pick-and-rolls isn't as frequent with the Timberwolves (7-29), leading to some frustration as the losses have piled up.
"I can't even explain how big of a change it's been," Flynn said Thursday. "It's tough. I'm still learning. Thirty-something games in, I'm still trying to find my place and see where I can be effective. It's just been tough, especially with the losing. But hopefully it'll start clicking and I think I can get back to being my old self."
Flynn is averaging 14.2 points and 4.0 assists per game, numbers that put him near the top of this year's rookie class. Like most rookies, however, there have been ups and downs.
He had 28 points and five assists in a stunning win at Utah on Dec. 14.
Then there are nights like Wednesday, when Flynn had six points on 1-for-11 shooting with four turnovers in a home loss to Golden State. He played only 25 minutes because Rambis was unhappy with Flynn's ability to get teammates involved and orchestrate the offense.
"It's part of the stubbornness of young ballplayers, inexperienced ballplayers," Rambis said, taking pain to point out that Flynn wasn't the only Timberwolves player who was struggling with it. "If they don't have something that's created for them, they don't feel like they're involved and then they're going to try and make themselves involved. All that does is create more problems for them."
Flynn had a quick rebuttal that showed the lessons he is learning are not always easy to embrace.
"If something's not going right on the court, you're going to try to dictate something because that's what you know how to do," Flynn said. "It might be a wrong thing at some times, but that's just instincts of a basketball player. When things are going wrong, you're going to try to make something good out of it."
Rambis likened the process to a parent teaching a child. The child doesn't always agree with what he is being told, but one day realizes the message was the right one. The coach has been quick to applaud Flynn's willingness to listen and says he envisions him one day becoming one of the top point guards in the league.
"I think he's terrific. I've put him in a system that's difficult," Rambis said. "It goes against the way he grew up playing. I've asked him to be more of an organizer, a floor leader, and learn how to do point guard things at a very young age with a young team. He's had some frustration dealing with that. But overall, he's done an incredible job doing the things I've asked him to do."
Flynn's backup, third-year veteran Ramon Sessions, has had similar difficulties.
"This is a pass-first system," Sessions said. "I'm used to having the ball, controlling the ball in pick-and-rolls and the regular stuff. It's a lot different and we just have to adjust to it."
The adjustments have been slow to come, and the frustrations have been easily seen on Flynn's expressive face.
"It's tough learning this system because it takes your instincts out of it," Flynn said. "You have to do a lot of reading and a lot of reacting to what the defense dictates."
Through it all, Rambis has tried to keep the lines of communication open, and their relationship is still a work in progress.
"We talk," Flynn said. "I wish our relationship was a little better, but we talk, though. He's a guy that I always go to and talk about anything I want. He pulls me to the side and talks to me. We definitely have a player-coach relationship."
Rambis isn't going to let up on either point guard. The way he sees it, the success of this offense, and the team, rests on their shoulders.
"I'm going to continue to be very tough on both of them," Rambis said. "They're such an integral part of what we do on both ends of the floor and they have a lot of responsibility. So much of our success begins and ends with them."
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