The Toronto Raptors aren’t exactly finding themselves in an advantageous situation these days.

During free agency this summer, they lost former All-Star point guard Fred VanVleet for nothing, when he signed a three-year contract with the Houston Rockets worth $128.5 million.

This season, they’re looking at three contractual hurdles, all of which – if mismanaged – could lead to similar outcomes as the VanVleet situation by the summer of 2024.

Pascal Siakam is in his final year of his deal, earning just over $37.8 million. While clearly an All-Star, and one of the better two-way players in the entire league, the Raptors risk losing him for nothing if they don’t trade him before the trade deadline, or extend him.

However, the organization does not seem interested in offering Siakam a new deal, at least not one worth maximum money, which means their option is really down to one final element: Moving him in a trade.

However, with less than a full year left on his deal, Siakam’s trade value likely is nothing but a shadow of what it used to be, meaning the Raptors won’t get as big a return for him as they could at last season’s trade deadline.

As such, the Raptors might have to settle for a return that’s 50-60 cents on the dollar, which is never an optimal situation to be in when the player in question is of star caliber.

Will a trade of Siakam, that lands the Raptors a package that’s made up of Buddy Hield and, say, Benedict Mathurin be enough to turn the team around? Not likely.

Toronto finds themselves in a similar situation with forward OG Anunoby, although certain variables are different. For one, the Raptors more than likely would be willing to extend Anunoby’s contract, but given the league’s 140% extension rule, odds are strong that Anunoby will decline that offer, as he can earn more on the open market.

Anunoby is earning just over $18.6 million this season, and has a player option for next season at $19.9 million, which he’s likely to decline.

Once again, the Raptors find themselves in a position of having very little say. They can trade Anunoby if they so desire, but once again they’ll have to accept that the market won’t pay full price for his services, given his contractual uncertainty.

Making the Anunoby situation even more difficult is the fact that whatever team trades for him will find themselves in the same extension situation as the Raptors do, meaning no team will be able to offer him an extension that makes sense for him.

(An extension offer tops out at a starting salary of $26 million, which seems low for one the league’s better 3-&-D players.)

Finally, there’s the situation with Gary Trent Jr, who could have been an unrestricted free agent this summer, but picked up his $18.5 million player option. He’s now looking to enter unrestricted free agency next summer, unless the Raptors trade him, or extend him.

Trent Jr isn’t in the same category of player as Siakam or Anunoby it should be noted. He’s struggled mightily this season, scoring just over 10 points per game, and hitting under 38% of his shots.

The Raptors will need to figure out if he’s worth extending, or if they should just take whatever they can get on the trade market.

There is the possibility that Toronto could take on a better player, who’s on a longer deal, which would sacrifice some of their future cap space. That idea shouldn’t be dismissed out of hand, particularly if the Raptors could re-package that player in a trade down the road for a better return. It’s time consuming, and they’d need to get the right player into their fold, but it’s an interesting option they should look into.

Because at the end of the day, these Raptors have painted themselves into a corner, by being passive in their salary cap administration, and not proactive on the trade market.

As of right now, it would make the most sense for them to lean into a rebuild, with Scottie Barnes being a key figure in that process.

Of course, they could roll the dice yet again, and let all of Siakam, Anunoby, and Trent Jr reach the open market, and hope they return on reasonable contracts. But given what happened with VanVleet just a few months ago, that’d be an enormous gamble, and one that could sink the franchise for years if it doesn’t pan out.