But he's never looked back.
"I think it was the best move for me," Wiggins said this weekend during the NBA all-star festivities. "It gave me more room and put me in a position where I could grow up faster. In the league, that's always what's best for you."
Had he stayed on Cleveland's star-studded roster, Wiggins knows he wouldn't be getting the same opportunities he's had with Minnesota, where he has quickly proven he has what it takes to be a future superstar in the league.
"There I would have been more of a role player," he said. "Here I'm getting more time to shine and do what I was put in this league to do. And I'm enjoying the process."
Wiggins' game has been steadily improving with each month of NBA experience. He has been especially successful in 2015, averaging 19.8 points, 4.6 rebounds and 2.5 assists per game for the month of January.
The 19-year-old swingman from Vaughan, Ont., has also made the Cavaliers well aware of what they let go, scoring 33 and 31 points against them in two games this season.
He wasn't among the all-stars this weekend but he did make his mark in the Rising Stars Challenge at Barclays Center, scoring 22 points to lead Team World to a 121-112 victory over Team U.S.A. en route to being named the game's MVP. He also wowed the crowd by throwing down a few dunks.
"He's really a leaper," Timberwolves teammate Shabazz Muhammad said. "It's just so easy how he jumps. That's something that's really a gift for him. His skill set has been really improving and that's something I've been really pleased with."
With a low-key demeanour, Wiggins can be a difficult player to read. But judging by the perma-grin on his face when he is around his teammates, he's had no trouble building a rapport in Minnesota.
"He's really shy with the media," Muhammad said. "He's a funny guy. If he's comfortable with you he's really talkative."
But it took time for Wiggins to gain that comfort level with his teammates after the trade happened.
"I think at times, at the beginning of the year he was trying to find his identity, especially with our team," Muhammad said. "He was shy with our team, too. We really embraced him and he's really starting to get comfortable and you're starting to see it on the court."
Second-year player Victor Oladipo faced off against Wiggins in Friday night's Rising Stars. A second overall pick of the Orlando Magic in 2013, he understands first-hand the challenges Wiggins has faced.
"The NBA game is very different from college," Oladipo said. "It's something you really have to get used to. It's something that doesn't come overnight. It's a process.
"As the game slows down and as he figures out where his spots are on the floor, he figures out how teams are guarding him, the game gets easier. It's a lot of room to grow for him. The sky is the limit (for him)."