TORONTO – VanVleet apparently turned down a four-year, $114 million contract extension last summer. The guard turned down a four-year, $114 million contract extension offer from the Toronto Raptors last offseason, according to TSN. VanVleet wants a contract worth at least as much as the $130 million over four years that Tyler Herro signed with the Miami Heat. Herro has a player option for 2023–2024 and may become an unrestricted free agency this summer.

Whether he will receive such a deal from the Raptors or someone else is unknown. The veteran has had a difficult season after becoming an All-Star for the first time in 2022. While his scoring, rebounds, and assists have all slightly declined, his 3-point shooting has drastically reduced. Through 31 games, he has averaged 18.8 points, 4.1 rebounds, and 6.2 assists while shooting 37.1 percent from the floor and 32.5 percent from outside the arc.

One thing that hasn’t changed from last season is his enormous workload. The Raptors don’t have a quality backup point guard or a lot of offensive productivity outside of VanVleet and Pascal Siakam. As a result, he is once again among the league leaders with 37.1 minutes played per game. In fact, in the entire league, only his teammates Siakam (37.3) and OG Anunoby average more minutes played per game than VanVleet (37.2).

The Raptors are currently mired in a vicious cycle with this group of players. They need VanVleet to be on the floor as frequently as possible to stay competitive, but the more he plays, the worse he gets. The more he breaks down, the worse he performs. The worse he plays, the more games the Raptors lose. In an effort to turn things around, the Raptors must use VanVleet more frequently as they lose more games.

In light of VanVleet’s decision to reject the extension offer throughout the summer, all of this should make for a very intriguing trade deadline. After a valiant first-round playoff exit last season, the Raptors were anticipated to once again be in the middle of the pack in the Eastern Conference. They weren’t top contenders, but they were unquestionably playoff teams with promise if Scottie Barnes continued to improve.

They are 16-23 and in 12th place halfway through the season, 1.5 games from the play-in round and 5.5 games from a top-six spot. In games decided by three points or less, they have a 1-7 record, and their health has not been great. You could claim that they may be a little better than their track record suggests. They remain more clearly apart from the conference’s elite clubs than anyone had anticipated. The key question is whether the Raptors front management thinks they can get there with just one or two transactions or whether they need to rebuild from scratch.

The Raptors have always preferred competition, with the exception of the unusual COVID season in Tampa, and according to TSN, the front office has no immediate plans to sell VanVleet. That might change, though, if the team keeps having trouble and is already out from the playoff chase early the following month.

The VanVleet contract controversy will always cast a shadow over everything. He is a small guard who has only ever participated in more than 65 games in his career, is over 30 years old, and has just been given a lot of work. Even if the Raptors want to keep him, it would be understandable if they are unwilling to commit a significant amount of money to him. You face the risk of losing him for free this summer if you don’t deal with him before the deadline if someone outbids you. 

Masai Ujiri was put in an awful predicament, yet the Raptors made him make these tough decisions, making him the highest-paid executive in the NBA. His chance to shine has arrived.