After being acquired by the Knicks at the 2023-24 trade deadline, the Raptors swiftly committed to Quickley long-term by signing him to a five-year, $175 million contract in June of 2024. The Kentucky product was expected to serve as a key piece in the franchise alongside Scottie Barnes and RJ Barrett. Still, Quickley missed 30 of Toronto's first 33 regular-season games due to pelvic and elbow injuries and had scheduled rest days over the final quarter of the season. Quickly has the scoring punch and playmaking ability to lead an offense, but health will be a big question mark for him heading into his second full season with the Raptors. The challenge facing Quickley will be how to balance the offense, given that Barnes, Barrett and a healthy Brandon Ingram will all be asking for the ball. Quickley's usage and shooting output will probably dip, but he could make up for that with an uptick in assists; he averaged a career-high 5.8 dimes per game last season.