Summary
After having real production in his first two seasons and proving to be a steal as the 25th pick in the 2020 draft, Quickley took a big leap in '22-'23, proving to be a real scoring threat and finished second in 6th Man of the Year voting. With similar players such as Anfernee Simons, Tyler Herro, and Jordan Poole all getting big contracts in recent seasons, Quickley could be next in line.

Offensively, Quickley is a threat with the ball in his hands either in pick-and-roll situations or isolations. He has real shake off the dribble, and uses his speed to get in the lane. Quickley is a three-level scorer, hitting 67% at the rim, 50% from floater range, and 37% from 3 in '22-'23, all rates that were above-average for his position, according to Cleaning the Glass. His midrange numbers took a slight dip in '23-'24 but his overall true shooting was similar due to him hitting 39% from three. Quickley really likes taking runners, and will even take them from fairly deep. 

Quickley also could improve his passing, as he has generally been a low-assist player. He can make the right reads when needed, but isn't someone that is manipulating defenses with his vision, and will sometimes miss the open pass.

Defensively, Quickley has good length and competes hard on that end. He isn't disruptive, as he posts low steal and block rates, but he rebounds well for a guard. However, at 6'3" and skinny, Quickley can get overpowered by bigger wings, and I could see him getting targeted in later rounds of the playoffs. Those are first world problems, but could stop him from becoming someone that can close games in the most important situations. 

Overall, Quickley has proven to be an effective scorer and someone that will shoot well from 3. It's unclear if he will continue to be as efficient as he was during his breakout with the Knicks, but if he does he will be someone that has a long career and makes close to $200 million. Even if he tops out as a semi-efficient bench scorer in the mold of Jordan Clarkson, that would also be a very successful outcome, despite being slightly disappointing considering how much promise he has shown thus far.
 
Cap Considerations
Quickley will be a restricted free agent with a $12.5 million cap hold, $8.5 million Qualifying Offer, and full Bird Rights. I wouldn't expect Quickley's QO to come into play, as he will likely sign a large contract with the Raptors or a large offer sheet elsewhere.

If a player has a smaller cap hold than his starting salary, his team can use cap space to sign-free agents before using Bird Rights to re-sign its own free agents. If the Raptors operate under the cap, they will be able to take advantage of this rule.

Depending on how close the Raptors are to the luxury tax after free agency, if Quickley is brought back by the Raptors on a multi-year contract they could benefit from frontloading his contract, as it could give them additional flexibility in the future. 

From other teams, Quickley will be looking for a 4-year, $100+ million offer, and it would likely take something over that in order for Toronto to not match. In addition, the team signing him to an offer sheet adding a 15% trade bonus, a player option, and some advances on his salary could make it more difficult for Toronto to match. Since Quickley will gets offers above the full MLE, only teams with cap space will be able to sign him, unless a sign-and-trade occurs, which would be complicated by base-year compensation rules.