At 6:00 pm on Monday night, the deadline for the Raptors to get an extension done with Delon Wright passed. Now they have to wait for the summer before they can negotiate again. For many reasons, this seems like it might be the beginning of the end of Wright’s time with the Raptors.

Why Wright is likely to be gone:

Due to the late start to his NBA career, Delon Wright will be 27 when his rookie contract runs out next summer. If he were 24, like Fred VanVleet was when he signed his two-year $18 million deal this summer, then maybe his current outlook would be different. But, at 27, it is pretty doubtful that a bridge deal will be in Delon’s plans. He is in his physical prime. This is the approximate age where NBA players typically make the most of their career earnings. Wright will likely be looking for the biggest offer available, and it can be very difficult for contending teams to justify paying any kind of premium for their best bench players.

Look no further than Boston and the current Terry Rozier situation for a more extreme example of a bench player becoming too good for the pond they’re swimming in.

The Raptors are already pretty capped out. They’ve already got money committed to two other point guards. And it seems that Masai wants to leave open the option for a rebuild in 2020. With that in mind, a long-term deal to a good, middle-aged bench player like Delon just doesn’t make sense.

Even if Wright is open to a one or two-year bridge deal, it is unlikely to be with Toronto. A bridge deal is, ostensibly, a short-term prove-it contract for a player to try and prove that they’re worth a far bigger contract. If Wright were to sign one, it would be with a team in desperate need of guard help, where he could possibly even secure a starting spot.

Meanwhile in Toronto, last year’s G-League MVP is the Raptors’ fourth-string point guard. Even with his dual position flexibility (point guard and shooting guard), the path towards the starting lineup for Wright in Toronto is just too convoluted for it to be a realistic option over somewhere like Orlando or Phoenix.

A Trade?

Will Delon Wright be traded this year? As of right now, probably not. But it’s definitely going to remain an open option in Masai’s mind as the season progresses.

You might think that everyone’s spot in the Raptors’ 10-man rotation is pretty secure, but I’d disagree. After Leonard and Lowry (and on some level, Valanciunas), it’s a free-for-all. The right streak at the right time, the wrong slump at the wrong time, injuries, etc.; almost everyone’s spot is up for grabs. Sure, there’s a current ranking of players that Nick Nurse will start with, but that ranking is immediately and constantly subject to change. Just look at how long it took for Norman Powell to fall from golden child to benchwarmer. Conversely, look at how long it took for Pascal Siakam to rise from low-skill, energy guy to possibly the most talented player on the bench.

A Norman Powell renaissance could singlehandedly make Delon Wright an expendable piece, leading to a trade. I believe that that could happen just as much as I believe that Wright and Lorenzo Brown could make Fred VanVleet expendable. That’s not sarcastic. The NBA season is chaos. Delon Wright is just as close to taking over as the starting shooting guard as he is to not playing at all. There is going to be an unbelievable amount of in-competition between Raptors players this season. Any trade made Masai Ujiri will be a trade of circumstance.

An Anticlimactic End

As it stands now, the most likely path for Delon Wright is probably him just walking in free agency. Masai has a history of getting value out of players that he feels are no longer needed, but he might find that there isn’t a strong trade market for Wright like there was for Greivis Vasquez. At that point, he might just decide that it’s better to have Delon on the team for the playoffs and risk letting him walk next summer.

As a conclusory side note; the comparison of Delon Wright and Fred VanVleet has always intrigued me. On the surface, they’re about as different as two players can be. But they seem to accomplish exactly the same things. Look at these statlines from last season:

Delon Wright: 20.8 minutes, 8.0 points, 2.9 assists, 2.9 rebounds, 1.0 steals, 1.1 turnovers, +11 net rating, .574 true shooting %, 1.7 VORP

Fred VanVleet: 20.0 minutes, 8.6 points, 3.2 assists, 2.4 rebounds, 0.9 steals, 1.0 turnovers, +9 net rating, .556 true shooting %, 1.5 VORP

The two operated at a virtually identical level last season, and yet they are both looked at very differently right now. One is being groomed as the potential heir to Kyle Lowry, while the other’s window with the team appears to be slowly shrinking. It all just goes to show how thin the line is for success in pro sports.

How different would Delon’s career be right now if he hadn’t been forced to go JUCO as a result of poor grades in high school? How different would it be if he’d never torn his shoulder in his rookie season with the Raptors? Or if the timing of his and VanVleet’s contracts ending were reversed?

These kinds of questions are what make basketball so interesting, and they’re also what the regular season is meant to answer. Something is definitely going to happen with or about Delon Wright’s current situation this year, so add that to the list of narratives that you’re paying attention to this season.