Looking at Instagram posts of Kyle Lowry rolling into to work in the Florida sunshine this past season in his Ferrari 812 GTS, top down, doubtless having already got a round of golf in and you had to ask yourself:
Would he ever give that up?
We’re about to find out. NBA free agency is scheduled to open Monday night at 6 p.m. ET and while deals can’t be confirmed until noon on Aug. 6 teams and player agents have been working on possibilities and frameworks for weeks, or even months now.
Which is why the rumblings -- or at least the more urgent ones -- about free agency began Sunday afternoon, more than 24 hours earlier than teams are ‘allowed’ to negotiate.
And a lot of those rumblings have Lowry at the epicentre and the Miami Heat as his destination, though there is enough froth in the market that things could change on a dime -- well, more like an extra $20 million or so, but you get the point.
What is evident is that Lowry -- the greatest player in Raptors history -- won’t have to put the ride in storage for the winter, and won’t be looking for a Bridle Path rental with a golf simulator in the basement.
It’s a mutual decision. The Raptors haven’t completely closed the door on Lowry returning -- anyone who’s followed the burly point guard’s previous forays into free agency knows that he’s always been eager to test the market but three times before -- twice in free agency and once by contract extension -- he’s had the Raptors ready and willing to step up and offer him the best deal out there.
But this time seems different.
From the Raptors' point of view, they seem ready to lean into a new future and different timelines. Their focus is on building a winning team around their core of 20-somethings while hoping that just turned 20-year-old Scottie Barnes, taken fourth overall last week, can evolve quickly enough to help in that cause.
It’s not that they believe they’re better off without Lowry but as long as he’s a Raptor, it will be hard for the existing team to take its new form.
“Fred, Pascal, OG they’re not the bench mob anymore, they’re [five and] six-year vets, as long as Kyle is around there’s always going to be a little brother thing going on,” was how one source close to the organization put it.
And while the Raptors understand Lowry’s value better than anyone, they don’t feel this is the time to try to compete if other teams are willing to guarantee the 35-year-old three seasons for as much as $90 million.
Meanwhile, Lowry is trying to thread the needle on what will be his last major contract, one that will likely take him through his 18th NBA season and push his career earnings up and over $275 million.
He wants his money -- “it’s a big ask and it should be,” said one league insider -- but he wants a chance to win and he wants to do it somewhere he’ll be happy to live with his family.
Miami -- just a year removed from the NBA Finals and always in win-now mode, it seems -- checks pretty much every box.
But they’re not his only suitor. The difference Chris Paul made to the Phoenix Suns as an elite veteran point guard caught the league’s attention.
With the expectation that Paul -- also a free agent having opted out of the last year and $44 million left on his deal as a 36-year-old -- will re-sign with Phoenix, Lowry has become the next best option.
But both New Orleans -- desperate to prove to Zion Williamson that they can build a winning culture around him -- and the Dallas Mavericks, looking to get help for Luka Doncic, have made moves in the past week to signal their intention to make a run at Lowry.
The result is the Pelicans are in a position to offer Lowry a deal averaging $30 million and -- according to sources -- are the most likely to be willing to guarantee a third year.
Similarly, when the Mavericks traded Josh Richardson to the Boston Celtics, the instant interpretation was that the goal was to create enough space to go after Lowry. They did that, but since they also want to re-sign Tim Hardaway Jr., there might be a possibility of a sign-and-trade that nets the Raptors a piece or two, maybe Canadian big man Dwight Powell and reserve point guard Jalen Brunson, as Mavericks beat reporter Tim Cato suggested in The Athletic.
And that’s without going into what the New York Knicks -- sitting on the most cap space in the league -- or Lowry’s hometown Philadelphia 76ers, who are desperate to finalize their divorce with Ben Simmons, are planning.
The thinking in those scenarios is the Knicks are determined to keep their powder dry to be the preferred landing spot for Damian Lillard if the Portland Trail Blazers star asks for a trade, as has been speculated.
Meanwhile, the perception around the league is that Sixers president Darryl Morey has been too aggressive in his asks for a return for Simmons to find a fit with any team at the moment and his unwillingness to sign Lowry to a longer-term deal remains an obstacle.
As well, while Lowry’s affection for his hometown is real, he’s aware that playing at home comes with its own set of complications.
Translation: Lowry -- who would have to approve of any sign-and-trade arrangement -- is unlikely to end up in Philadelphia.
So where does this all leave the Raptors?
There is some exposure, undoubtedly. If Lowry is signed as a free agent into cap space in Dallas or New Orleans, Raptors president Masai Ujiri and general manager Bobby Webster would be faced with losing five of the top six players from the rotation of the 2019 championship team without getting anything in return, with Lowry joining Kawhi Leonard, Danny Green, Serge Ibaka and Marc Gasol as free agent departures.
Even with all the credibility Raptors management has earned over the years, it’s not an ideal scenario.
But the buzz around Lowry could work in the Raptors' favour.
With Dallas and New Orleans circling, Lowry’s price has been driven up.
At one point the Heat could have conceivably signed Lowry into cap space -- they could comfortably get to about $23 million -- and with the advantage of the address, the weather and the lack of state income tax in Florida may be the preferred choice among the credible offers.
But with the potential of Lowry getting multiple offers in the three-year, $90 million range, the Heat are incentivized to look at options like a sign-and-trade with Toronto.
In that scenario, the Raptors would sign Lowry using their Bird Rights and then trade him to Miami.
The Heat picked up the option on the final year of Goran Dragic’s $19.4 million contract on Sunday, eating up their cap space and signalling their intention to operate as an ‘over-the-cap’ team, meaning they would need the Raptors' help to acquire Lowry. It would also provide them access to the full mid-level exception for teams above the salary cap that they could in turn use to add around a core of Jimmy Butler, Bam Adebayo and Lowry.
In a sign-and-trade, the salaries would need to match, more or less. Longtime Heat beat reporter Ira Winderman suggests the deal could be a simple as the Raptors signing Lowry for three years at $81 million with the Raptors taking on Dragic, the Heat’s still capable 35-year-old point guard.
The Raptors would then have the option of trading Dragic -- possibly to one of the teams that missed out on Lowry -- or simply buying out the Slovenian veteran and regaining some cap space.
Why would the Raptors be so accommodating?
Perhaps they could lean on the Heat to throw in second-year centre Precious Achiuwa or third-year wing KZ Okpala, both of whom are representing Nigeria at the Olympics, which can’t hurt their standing in the eyes of Ujiri.
Of course, Lowry isn’t the Raptors' only concern in free agency.
The fate of fourth-year guard Gary Trent Jr. is up in the air. He’s a restricted free agent so the Raptors control his fate, but given he’s represented by Rich Paul -- no stranger to driving a hard bargain on behalf of his clients at Klutch –- it shouldn’t be a surprise if the Raptors get tested to some degree.
According to league sources, the sharp-shooting wing could be looking for a deal in the range of $50-plus million over three years.
The Raptors would likely want to do something cheaper, but if there is $17-$18 million a year in the marketplace for a 22-year-old who has averaged double-digits in scoring and 39 per cent from three on a high volume of attempts, they might have their hand forced.
The Raptors' biggest need in free agency is to fill their vacant centre position and do it better than they did last season when they started training camp with Alex Len and Aaron Baynes as the projected platoon.
The Raptors would be open to bring back Khem Birch at the right number and Kings free agent centre Richaun Holmes has long been thought a Raptors target. But according to sources, the Raptors might be looking at the trade market to shore up their void in the middle, with the Kings working hard to re-sign Holmes who is believed to be looking for a deal comparable to Myles Turner’s $80 million over four years. That’s not to say he’ll get it, but just to point out that Holmes is looking to cash in.
Answers will be forthcoming and the clock is ticking, but one thing that seems more certain by the minute is Kyle Lowry won’t be looking for winter tires for his Ferrari. Or be playing for the Raptors next season.
