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As the Toronto Raptors continue to wallow below .500 and out of the Eastern Conference Play-In Tournament picture, trade rumors swirl around most of their roster. Recent reports say the Raptors will “do something” before the February 9 trade deadline. Toronto President Masai Ujiri isn’t one who is content to sit in the middle, so expect the Raptors to pick a direction soon. They’ll either be all-in or they’ll be resetting the roster ahead of a busy offseason.

One player caught in the center of all of this swirl is veteran point guard Fred VanVleet. Recently, VanVleet addressed his contract and potential extension negotiations with the Raptors. He didn’t say much beyond his loyalty is with the Raptors. On reports that he turned down a contract extension, VanVleet’s response was that there hadn’t been an offer made for him to turn down.

That’s all well and good, but a player of VanVleet’s caliber is going to be made an extension offer. Even if an official one hasn’t been made, VanVleet, his reps and the Raptors know what the max they can offer him is. The other option is that VanVleet could play things out and immediately become one of the best players on the free agent market this summer. Let’s look at what VanVleet’s next contract could look like.

The Veteran Extension

The most beneficial extension scenario for Fred VanVleet would be to decline his player option for next season. This would allow him to add four years via an extension. If VanVleet opted in for next season, he’d only be able to add up to three years. He could wait, and extend after opting in, but that’s probably not something that’s on the table.

In a four-year extension by declining his option, here’s what VanVleet’s deal would look like:

    • 2023-24: $25,500,000
    • 2024-25: $27,540,000
    • 2025-26: $29,580,000
    • 2026-27: $31,620,000
    • Total: four years, $114,240,000

That’s a bump of 20% over VanVleet’s current $21,250,000 salary with 8% raises on top of that.

This deal would give VanVleet an average annual value (AAV) of $28.56 million. That’s well below his max salary, but in range of what a realistic salary could be if VanVleet opted for free agency.

For reference, $25.5 million would make VanVleet the 14th highest paid point guard next season. He’d be right behind Jalen Brunson and just ahead of Mike Conley. That feels about right for VanVleet, as far as company goes. Non-All-Stars, but right at the top of that next tier down.

Given that company, the dearth of quality free agents next summer and the need to have a good point guard, we have to ask: could VanVleet do better by simply opting out and hitting the open market?

Re-signing with the Raptors as a free agent

Toronto’s leg-up on the competition to re-sign Fred VanVleet is that they can offer him a fifth year and they can offer him 8% raises vs being limited to four-years deals with 5% raises. The max VanVleet can get in free agency from Toronto looks like this:

    • 2023-24: $40,200,000
    • 2024-25: $43,416,000
    • 2025-26: $46,632,000
    • 2026-27: $49,848,000
    • 2027-28: $53,064,000
    • Total: five years, $233,160,000

That’s the full 30% of the cap max, with 8% raises and the max of five years.

This deal would immediately vault VanVleet into third place in salary among all point guards, behind only veteran superstars Stephen Curry and Damian Lillard. He’d be ahead of Luka Doncic and Trae Young (in the second years of their Designated Rookie extensions) and on par with someone like Ja Morant (who seems destined to quality for a Designated Rookie extension).

If you blanch at that kind of money for VanVleet, don’t worry. You aren’t alone. He’s not getting a full max deal. We’re simply setting the high-end that he could sign for. History tells us VanVleet will land somewhere south of that $40.2 million number in first-year salary.

Signing with another team as a free agent

Fred VanVleet is going to fall somewhere between the top-five and top-10 on available free agent lists this summer. We’ve got him ranked fifth overall, and the players in front of him (James Harden, Kyrie Irving, Draymond Green and Khris Middleton) are more likely to re-sign with their teams than they are to leave.

That could put VanVleet in play to be the best free agent to actually change teams this summer. We’ve already got reporting that the Phoenix Suns and Orlando Magic could be interested in acquiring the veteran point guard to lead their offenses.

Here’s the most a rival team could offer VanVleet:

    • 2023-24: $40,200,000
    • 2024-25: $42,210,000
    • 2025-26: $44,220,000
    • 2026-27: $46,320,000
    • Total: four years, $172,860,000

That’s the same 30% of the cap in first-year salary, but the max another team can offer VanVleet is four years and 5% raises.

We’ve already covered where that would place VanVleet among his peers at his position next season. That’s probably not in play.

One other thing to be aware of: This is the most VanVleet could get via a sign-and-trade too. That’s important because of something we’re going to cover next.

The Extend-and-Trade or Extension After a Trade

Extend-and-trade deals are rare, because they don’t really offer all that much for the player. They’re limited to a 5% bump in salary over their current salary and then adding one more year at an 8% bump. In Fred VanVleet’s case, here’s what it would look like for him in the new years of an extend-and-trade:

  • 2023-24: $22,312,500
  • 2024-25: $24,097,500

That’s over $46 million in new money, but that’s not really where VanVleet is at. He’d also make roughly $500,000 less in the first year of an extend-and-trade than he would by simply opting in with Toronto for next season.

It’s important to note that any team trading for VanVleet can’t extend him immediately either. They’d have to wait for six months to extend him for more than he could get via an extend-and-trade. At that point, it’s probably best for VanVleet to simply opt out and sign a new contract as a free agent.

The Opt-In-And-Trade

Given the reported interest in Fred VanVleet on the potential free agent market, we’re going to cover the idea of an opt-in-and-trade. For example, one of the teams mentioned as a potential landing spot for VanVleet is the Phoenix Suns. If Phoenix is convinced that Chris Paul doesn’t have it anymore (he’s slipped greatly this season), they could look to move on and replace him with VanVleet.

However, Phoenix won’t have the cap space to sign VanVleet outright. And doing a sign-and-trade would subject Phoenix to the hard cap. That makes it tricky to add much salary and to maintain roster flexibility.

Thus, we could see VanVleet opt in for next season under the auspices he’d be traded to Phoenix this summer. Because it would be a straight trade, the hard cap wouldn’t be triggered. And, after a six-month waiting period, Phoenix could do a four-year extension with VanVleet. That deal would look like this:

    • 2023-24: $22,824,074
    • 2024-25: $27,388,889
    • 2025-26: $29,580,000
    • 2026-27: $31,771,111
    • 2027-28: $33,962,222
    • Total: five years, $145,526,296

That’s VanVleet opting in for next season, then extending (after a six-month waiting period) to add four new years. That would follow the Veteran Extension math of a 20% bump in first-year salary, followed by 8% raises on each new year.

As you can see, this could leave a good deal of money on the table over simply signing with a team outright as a free agent. The benefits here are that it allows the acquiring team to avoid becoming hard capped, while allowing VanVleet to still add several years of new money to his deal.


Fred VanVleet’s contract situation isn’t as cut and dry as many others. He’s not a clearcut max player, so there isn’t an obvious reason for him to play things out to free agency. But VanVleet is also not a deep-career veteran who should take an extension to simply add more years to his deal.

Instead, we have a player who is firmly in the middle. We can absolutely rule out an extend-and-trade. That wouldn’t give VanVleet the money he’s earned, nor the safety of adding multiple years.

That leaves the standard veteran extension or hitting free agency. Given the market, VanVleet should probably forgo an extension, opt out of his current deal and become an unrestricted free agent this summer. That gives him the most control, plus allows for the same long-term security, while adding the ability to make the most money possible.

When suggesting VanVleet should opt for free agency, we need to consider who projects to have cap space. Eight teams project to have in the range of $30 million in cap space this summer. Of those teams, we can probably eliminate the Oklahoma City Thunder and Indiana Pacers as VanVleet suitors. They’ve got their guard positions covered for years to come.

The Los Angeles Lakers are interesting, but they are probably thinking bigger with their cap space. And if they aren’t thinking of adding a third star around LeBron James and Anthony Davis, the Lakers should be splitting their cap space up to add much-needed depth.

That leaves the Houston Rockets (they have guards, but are rumored to have interest in reuniting with James Harden so…), Detroit Pistons (if they don’t see Cade Cunningham as a point guard, and they’ve also had VanVleet interest before), Orlando Magic (guard rotation is very much in flux), San Antonio Spurs (Tre Jones is the only point guard on the roster) and the Utah Jazz (whole roster is in flux) as cap space suitors.

Of that group, VanVleet can carve out a market. And that’s before we even get to teams that could do a sign-and-trade with the Toronto Raptors.

Given that a market for VanVleet exists, it’s now about figuring out value. VanVleet will be 29 at the end of February, which means his next deal will cover his age-29 through age-32 seasons. He’s had some injury issues over the last four years, so he’s not exactly a young 29-year-old either.

Now, we have to combine that with some shooting percentages that have slipped to a dangerous level this season. VanVleet has always been an average finisher at the rim and more of a midrange and three-point specialist. Given his shot profile, shooting 40% overall, 37% on three-pointers wasn’t overly worrisome.

This season, VanVleet is under 40% overall and hitting just 33% of his shots from deep. That’s on a high volume of 8.6 three-point attempts per game too. If that’s a blip, whatever. If it isn’t, that’s a bad sign of things to come.

On the flip side, VanVleet remains a fairly rugged defender. He’s strong, so he can hold up against bigger players. He’s also a good rebounder for his position and a good playmaker. Ideally, VanVleet would be the guy who sets your offense and then spots up for open jumpers off others. A high-end organizer, if you will.

Having looked at all that, VanVleet is probably going to garner offers that pay him somewhat near, or above, $30 million in first-year salary. That would put VanVleet right in that Chris Paul/Kyle Lowry territory as veteran point guards who are just outside the top-10 in salary.

If a team were smart, given VanVleet’s age, injury history and potentially declining shooting, they’d frontload his deal. Give him more in Year 1 than what most think is fair, but the contract would then descend each year, to match any potential fall-off in play.

For the Raptors, that deal could look like:

    • 2023-24: $33,600,000
    • 2024-25: $30,912,000
    • 2025-26: $28,224,000
    • 2026-27: $25,536,000
    • Total: four years, $118,272,000

That’s the max-allowable 8% declines from year to year.

For a rival team, they could offer a declining structure that looks like this:

    • 2023-24: $32,000,000
    • 2024-25: $30,400,000
    • 2025-26: $28,800,000
    • 2026-27: $27,200,000
    • Total: four years, $118,400,000

That’s the max-allowable 5% declines each year.

In both scenarios, VanVleet gets roughly $118 million. In both scenarios, teams are protected in the early-30s years for VanVleet, in case his play falls way off. For reference, $26 million would be roughly 15% of a $170 million cap in 2026-27. And that could be low-balling where the cap will fall under a new CBA and with new media rights deals in place.

No matter where his next deal lands, Fred VanVleet should skip signing an extension right now. Unless he really wants to stay in Toronto long-term, and he might very well want to, he’s likely leaving money on the table if he forgoes becoming an unrestricted free agent this summer. Bigger offers should await him this offseason, whether they are from the only NBA home he’s known, or elsewhere.