Watch: How Dame was pranked about trade destination

"He's always joking around, so I called him and he didn't answer. Then he called me back and was laughing."

Despite Raptors general manager Bobby Webster telling SportsNet that Toronto made "the biggest offer we've ever made for a player," it wasn't enough for Portland, who agreed to send Lillard to Milwaukee on Sept. 27 in a three-team deal. 

Between Lillard and Giannis Antetokounmpo, Milwaukee features two of the most explosive offensive players in the NBA. Both are capable of scoring 40 points on any given night and on paper have complimentary offensive skill sets. 

Lillard showed in 2022 that he's still one of the NBA's best scoring guards, averaging a career-high 32.2 points per game in 58 contests last season while shooting 37 percent from deep and 7.3 assists per game. He's also a strong distributor with a career 6.7 to 2.8 assist-to-turnover ratio.

With Lillard joining veteran sharpshooter Khris Middleton in the Milwaukee backcourt, opponent defenses won't be able to simply collapse on Giannis when he drives to the basket. Instead, they'll need to stay home on Middleton and Lillard, theoretically creating more room in the paint for Antetokounmpo to excel on a nightly basis. 

Lillard said that he also thinks that he'll be able to take a step forward defensively with the Bucks. 

"At the very least, I'm going to go out there and compete," he said per clickondetroit.com, acknowledging he doesn't have a reputation as a great defender.

"I've had a lot of responsibility on the offensive end for my entire career. I think playing with the players I'll be with here, it will also give me the opportunity to show myself much better on the defensive end of the floor."

Other than injury, the biggest threat to the success of this pairing is ego. 

Both Lillard and Antetokounmpo are accustomed to being their team's primary offensive weapon. In 2022-23, Giannis recorded the highest usage rate in the NBA, with Milwaukee calling plays for him 38.8 percent of the time. Lillard finished fifth in the league at 33.8 percent.  

If head coach Adrian Griffin is able to keep both of his stars happy on offense, Milwaukee could easily play for their second NBA Championship in four years.