Toronto Raptors guard Fred VanVleet turned down a four-year, $114 million contract extension offer from the team last offseason, according to TSN. VanVleet, who has a player option for 2023-24 and can become an unrestricted free agent this summer, is looking for a deal worth at least as much as the one Tyler Herro signed with the Miami Heat -- $130 million over four years. 

Whether he'll get such a deal, either from the Raptors or elsewhere, remains to be seen. This has been a frustrating season for the veteran, who was a first-time All-Star in 2022. His scoring, rebounding and assists are all down slightly, and his 3-point shooting has fallen sharply. Through 31 games, he's putting up 18.8 points, 4.1 rebounds and 6.2 assists per game, while shooting 37.1 percent from the field and 32.5 percent from behind the arc. 

One thing that's stayed the same from last season is his heavy workload. The Raptors don't have a reliable backup point guard, nor much in the way of offensive creation outside of VanVleet and Pascal Siakam. As a result, he's once again among the league leaders in minutes per game at 37.1. In fact, the only players in the entire league averaging more minutes than VanVleet are his teammates, Siakam (37.3) and OG Anunoby (37.2). 

At this point, the Raptors are trapped in a vicious cycle with this roster. They need VanVleet on the floor as much as possible to stay competitive, but the more he plays, the more he breaks down. The more he breaks down, the worse he plays. The worse he plays, the more the Raptors lose. The more the Raptors lose, the more they need to play VanVleet to try to get back on track. 

All of which, combined with VanVleet's decision to turn down the extension offer last offseason, should make for a very interesting trade deadline. After a competitive first-round exit in the playoffs last season, the Raptors were projected to again be in the middle of the pack in the Eastern Conference -- not a top contender but a definite playoff team with potential upside depending on how much Scottie Barnes improved. 

Now, as we reach the mid-way point of the season, they are 16-23 and sitting in 12th place, 1.5 games out of the play-in tournament and 5.5 games back from a top-six spot. They haven't been super healthy and are just 1-7 in three-point games. So, you can make a case they are a bit better than their record shows. Even so, it's clear they're further away from the top teams in the conference than everyone thought. The big question is whether the Raptors' front office believes they're a move or two away from getting to that level or whether they need to tear things down and start over. 

Aside from the strange COVID season in Tampa, the Raptors have always leaned towards competitiveness, and per TSN the front office currently has no plans to deal VanVleet. However, if the team continues to slump and is well out of the playoff picture early next month ahead of the deadline, that could change. 

Regardless, the VanVleet contract situation will be hanging over everything. He's a small guard who has only played more than 65 games once in his career, is approaching 30 years old and has carried a tremendous workload in recent years. Even if the Raptors want to keep him, it would be totally understandable if they're wary of committing too much money to him long-term. At the same time, if you don't trade him at the deadline you then run the risk of being outbid this summer and losing him for nothing. 

The Raptors are in an unenviable spot, but making these tough decisions is exactly why they made Masai Ujiri the highest-paid executive in the NBA. This is his time to shine.