If Kyle Lowry wanted to he could ride off into the sunset a future Basketball Hall of Famer and enjoy a post-NBA career playing golf every day without any financial worries he could.
At this point, there's not much else for the 35-year-old guard to do. He's hoisted the Larry O'Brien trophy, he's played on a gold medal-winning Olympic team, he's been a six-time All Star, former All-NBA third teamer, become the greatest player in Toronto Raptors franchise history, and he's collected over $190 million in game cheques. There are only two things keeping him around these days: a love for the game and a desire to keep supporting his family and community for the years to come.
As he heads into the 2021 offseason for what could be his last significant payday as an NBA player those factors will be at the top of his mind.
"My family will be a major factor in this," Lowry said during his season-ending media availability Tuesday. "Also, money talks, and years talk, and all that stuff. Let's be real. I play this game for the love of the game but at the end of the day, I want to make sure my family is still taken care of for generations and the time to come."
Lowry wants his impact to be felt off the basketball court. In March, he told Business Insider that he wanted to help break down systemic barriers for people of colour.
"We don't want to just be sitting at the table with everybody else — we want to create our own table and bring people that we want to be in there, to have people of our color at the table with us," Lowry told Business Insider.
Those goals will once again be a deciding factor for Lowry who said he wants to continue to build his brand as an "ownership-type person" and an entrepreneur.
The Raptors are set up with the ability to offer Lowry more money than anyone else this summer. If they want him back and are willing to pay up both in terms of yearly salary and term, there's little question Lowry will be back playing at Scotiabank Arena sometime soon. But Toronto is at a different part of its developmental curve. The team has already locked up Pascal Siakam, Fred VanVleet, and OG Anunoby, and will likely have to spend a considerable amount to retain restricted free agent Gary Trent Jr. this summer and that could leave Lowry on the outside.
There will certainly be a handful of other suitors ready to pony up the cash for Lowry. Most notable among those are expected to be the Miami Heat and New York Knicks who both have the salary cap space to sign Lowry outright and can afford to offer him the kind of multi-year deal he's looking for. While the Philadelphia 76ers can't sign Lowry outright, they can work a sign-and-trade with Toronto if Lowry wants to return home to Philly.
Based on what Lowry has said regarding financials it sounds like the thing he's going to be focused on taking the deal with the highest total value. While a shorter term and higher average annual value might allow him to eek out one more contract, the security of a longer-term deal seems to be what interests him these days.
Then there's the championship and family side of the free agency equation. Lowry said he wants to find some stability for his family going forward. While that might indicate a preference for the Raptors, Lowry sold his home in Toronto and has spent the past few months living in Tampa, Florida. It's not entirely clear if moving back to Toronto is the most stable option for his family, especially if Lowry is eventually looking toward a post-NBA career outside of Canada.
As far as championship aspirations, it's hard to see Toronto being atop that list, especially with Miami lurking. If the NBA lottery balls bounce right and Toronto wins the top pick in the NBA Draft it's possible that the equation changes somewhat, but the Heat are just one year removed from reaching the NBA Finals with a core that remains mostly intact.
Every time Toronto has prepared to say goodbye to Lowry he seems to pop back up ready for next season. It became a bit of a joke during his final press conference which ended with a lighthearted goodbye until Raptors media day next season. It's true, his Raptors eulogies have been written many times before. But this time the ball is in his hands. The Raptors should want him back, but I wouldn't put my money on a Lowry return.