Fred VanVleet Faces Another Decision With Contract Extension Available: Bet On Yourself or Take the Money?

The Toronto Raptors can offer Fred VanVleet a contract extension this offseason, but will he take it or would he rather double down and test free agency?

Nathan Ray Seebeck-USA TODAY Sports

Fred VanVleet lives by a three-word slogan: Bet on yourself.

They're words that go back to his 2016 NBA Draft night party when he turned down opportunities to be a second-round draft pick and instead opted to go undrafted, betting on his skills that he could crack an NBA roster, stick around, and get to an earlier payday.

By now, you know how things played out. He made the Toronto Raptors roster and fast-forward a half-decade and he became the highest-paid undrafted player in NBA history.

"Only you know what you’re really worth," VanVleet's official website says under the tab for Our Story.

This summer VanVleet is going to be faced with another decision: Double down or hold? At 28 years old, he's entering the third year of his record-breaking four-year, $85 million contract and is set to make $21.25 million this season before he holds a player option at $22.82 million in 2023-24.

If he wants, he can ride out the season and, assuming he stays healthy and he plays at or near an All-Star level next year, he can opt-out of the final year of his deal and become an unrestricted free agent in the summer of 2023. Worst case scenario, he'll have that nearly $23 million cushion to fall back on should something go awry. In the best-case scenario, VanVleet takes his game to another level and signs something close to the five-year nearly $200 million max contract he'd be eligible for as an eighth-year player.

Alternatively, as of July 8, 2022, the second anniversary of his current contract, he and the Raptors can work out an extension of up to four years $114.2 million that would keep him in Toronto through 2026-27 and his age 32 season.

Operating over-the-cap this summer, Toronto will need to find ways to improve the team's depth. They'll also have a couple of extensions to consider for their 2 centerpieces, Fred & Pascal. Not mentioned below, but Banton & Brooks' contract also become Fully GTD on opening night. pic.twitter.com/cnJqlmWnU8

— Anil Gogna (@AnilGognaNBA) April 29, 2022

“I love having conversations," said VanVleet on the topic of offseason extension talks. "We’ll cross that bridge when we get there.”

The Bet on Yourself playbook would call for VanVleet to take another gamble. He's improved every season so far and he showed last year that he's one of the league's best point guards when he's healthy. Even at barely six-feet tall, he's a foundation piece for this Raptors organization, and someone Toronto has made it clear won't be moved this offseason.

Conversely, the security of a four-year, $114 million deal with the only organization VanVleet has ever known is nothing to scoff at.

VanVleet has always been a risk-taker when it's come to his contracts, but in the words of Kenny Rogers, sometimes, you've got to know when to hold 'em, know when to fold 'em, know when to walk away, and know when to run.

Further Reading

Can the Raptors be all about size and versatility with Fred VanVleet on the roster? Masai Ujiri explains why it works

Masai Ujiri drops a hint regarding Chris Boucher's upcoming free agency

Masai Ujiri gets emotional praising Pascal Siakam & Raptors forward explains what's next