Are Kyle Lowry and the Toronto Raptors Headed for a Divorce?

Jake Fischer@JakeLFischerContributor IFebruary 8, 2021

Toronto Raptors guard Kyle Lowry reacts to referee Natalie Sago (9) after he was called for his second technical foul during the second half of an NBA basketball game against the Sacramento Kings Friday, Jan. 29, 2021, in Tampa, Fla. (AP Photo/Chris O'Meara)
Chris O'Meara/Associated Press

With over 20 games already postponed this season, it's been difficult for NBA teams to evaluate their rosters. And the result is a muddied picture of who will buy and who will sell ahead of the league's annual trade deadline on March 25.

The biggest domino that could fall and may impact the title race: Kyle Lowry. There is a portion of Raptors personnel, league sources said, that believes the franchise should bid its beloved All-Star farewell and begin Toronto's next chapter in earnest.

"There's a time capsule for everybody and everything," said one Western Conference executive, "and it's probably just time to move on."

The Raptors, who still roster seven players from that 2018-19 title team, stand only 10-13 after a dreadful 2-8 start. Toronto never panicked, especially as four of those first eight losses were by five points or fewer. Nick Nurse's staff has developed rotation pieces in Yuta Watanabe and Deandre' Bembry of late, but the Raptors feel far removed from the Eastern Conference elites. None of Philadelphia, Milwaukee, Brooklyn or Boston would enjoy facing this current Toronto iteration as a low-seeded first-round opponent, but they wouldn't exactly fear them, either.

As much as Chris Boucher has emerged in the Sixth Man of the Year conversation, a gulf has so far proved to exist between starting center Aron Baynes and the Serge Ibaka-Marc Gasol combination Nurse had at his disposal a year ago. Toronto has all of its first-round picks to play with, yet the organization feels more in transition than a dark-horse contender that's one piece away.

It may be that Lowry, who's a free agent after this season, is the best trade chip for the Raptors' front office. He remains their third-leading scorer, top creator and a lethal three-point shooter, but his expansive role inevitably caps everyone else's.

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The Raptors just committed $85 million over four years to retain Fred VanVleet as the franchise's long-term ball-handler. If his 2019 Finals performance and 54-point outburst last week in Orlando were any indication, he's capable of handling full-time creation abilities. Of course, he still benefits from Lowry's own playmaking, but Toronto drafted another crafty combo guard in Malachi Flynn with the 29th pick in November for a reason.

"Young guys can't blossom until you move on from Lowry because the pecking order is still set from the top," one Eastern Conference coach said. "If you're trying to reshape your roster, one thing you need to avoid is duplication."

Michael Dwyer/Associated Press

Toronto, of course, has previously weighed moving Lowry on numerous occasions. From the onset of Masai Ujiri's Raptors tenure in 2013, the executive scanned the league for Lowry trade destinations and came inches shy of dealing him to New York.

Toronto also discussed Lowry before the February 2019 trade deadline with Memphis, according to league sources, and almost added him to that eventual Jonas Valanciunas package, which would have landed Mike Conley with the Raptors alongside Marc Gasol. Those negotiations were so advanced, sources said, Lowry himself was made aware of the talks, and Grizzlies officials even told other front offices they were nearing a deal. Toronto sniffed the market for Lowry before the 2020 deadline as well, sources said.

Finding a destination for Lowry may be more complicated this season. He'll turn 35 the day of the trade deadline, and his one-year, $30.5 million deal will be a huge number to introduce into a team's cap sheet.

Toronto does not appear interested in rebuilding. You don't rebuild after paying a combined $157 million to VanVleet and OG Anunoby the summer after inking Pascal Siakam to a $130 million deal. You retool. The Raptors have extended both Nurse and general manager Bobby Webster on multiyear deals. Regardless of Ujiri's future—he's in the last season of his own contract—Toronto prides itself on a tradition of winning and its seven straight playoff runs. The organization is committed to that core.

Moving Lowry will likely require a return which can both benefit the Raptors' immediate postseason aspirations and their long-term ceiling. That could mean adding a young player while eating a veteran salary, or gaining a seasoned playoff performer plus a draft pick. Perhaps all three.

Lowry's age and the length of his contract may limit his most likely suitors to championship contenders. And while they've been mired in their own slow start, the Heat still hold title aspirations and have long shown interest in Lowry. "He's a very Miami-type player," another Eastern team official said. "Gritty, tough."

Chris O'Meara/Associated Press

Goran Dragic became trade-eligible Feb 6. With the second year of his deal a 2021-22 team option, he's essentially on his own expiring contract, but because of his one-year Bird rights, Miami will need his consent to move him. Sending him to a Toronto team with playoff hopes might pique his interest. 

There are more cap gymnastics in play, and Miami has limited options in draft capital until 2025. It seems the Heat might have to part with one of Tyler Herro or Duncan Robinson to make any Lowry deal worth Toronto's while. The Heat have never appeared keen to move either, league sources said, yet it's uncertain how Miami's slow start will color the team's efforts to capitalize on this championship window with Jimmy Butler and Bam Adebayo in place. "You know with Pat Riley, nothing's off the table," one rival executive said.

The Clippers might have a cleaner path to landing Lowry. "I think Toronto would want to send him West," one Eastern team official said, "but Masai is going to do a deal that brings back the best package." The Clippers might be able to provide both. Los Angeles has made it widely known that Lou Williams is available, sources said, and there's a cohort in that front office ready to move on from Patrick Beverley as well—although the Clippers have been more in the market for a mid-tier guard than someone like Lowry, sources said. Adding someone of Lowry’s caliber, however, would boost L.A.'s best punch against the West's other heavyweights.

The Clippers could add Ivica Zubac and Mfiondu Kabengele to a Beverley-Williams package to make the salaries match, and that return would bring Toronto two young big men to fill the hole up front. The 23-year-old Zubac will still have two years, $14.5 million remaining on his current deal after this season (club option in 2022-23). He's a talented player on a contract that would intrigue most front offices.

Los Angeles declined to pick up the third-year option on Kabengele's rookie contract, and Ujiri is said to have a close relationship with his college coach, Leonard Hamilton—perhaps as close a relationship as Lowry holds with Clippers head coach Tyronn Lue. Lowry even texted Lue, remember, following the Raptors' Game 1 loss to Cleveland in the 2016 Eastern Conference Finals, wishing he could review film with the opposing play-caller.

Ashley Landis/Associated Press

From there, several teams on the periphery of the playoff picture could view Lowry as the missing piece to fortify their postseason run. The Magic are in dire need of ball-handling help having lost Markelle Fultz for the season, and it's worth mentioning that Orlando president Jeff Weltman arrived in Disney World after years helping steer the Raptors. But there's little optimism Lowry would re-sign in Orlando after this season, sources said, and teams are curious if the Magic finally emerge as sellers before this trade deadline after dangling Evan Fournier and Aaron Gordon prior to the draft and falling into another pedestrian regular season.

The math works easily if Toronto swapped Lowry straight up for Andre Drummond, and the Raptors did pitch Valanciunas to Detroit before that aforementioned Gasol deal, sources said, before Drummond landed in Cleveland. Adding Lowry would push the Cavaliers toward the top of the group of teams flirting with the final East playoff spots, but as much as his veteran savvy could benefit Cleveland's blooming backcourt of Collin Sexton and Darius Garland, he'd also soak up minutes that are integral to their development—just like he's doing in Toronto. 

New Orleans has so many draft picks, and the Pelicans could send various packages involving Eric Bledsoe, Lonzo Ball and JJ Redick—the three Pelicans guards who are widely known to be available via trade—and still reserve the capital for NOLA's primary target, Bradley Beal, if he ever signaled it was time for new scenery. But while teaming with Brandon Ingram and Zion Williamson would present an intriguing outcome for Lowry, taking back Bledsoe specifically could run the Raptors into the same redundancy issues they currently face.

Toronto, of course, doesn’t have to deal Lowry. He's such an intriguing player this trade season, however, because of the value he still brings, and the time may finally be right for the Raptors to part with the All-Star point guard who helped deliver the franchise's only title. A source added, "He's an expensive player with declining value; he may be a better fit for a championship-caliber team."

One last dark-horse option to keep an eye on: San Antonio. The 13-10 Spurs have jumped out to a stronger start than many around the league anticipated, and while trade chatter remains hushed, Patty Mills has been floated as an available name of late. The Spurs also own all their upcoming picks. Mills and Rudy Gay's expiring contracts could get it done and reunite Lowry with DeMar DeRozan.

Perhaps the best outcome of all would be Lowry and DeRozan tag-teaming against LeBron James once again. A next chapter, indeed. 

         

Jake Fischer covered the NBA for Sports Illustrated and is the author of Built to Lose: How the NBA's Tanking Era Changed the League Forever. Follow him on Twitter, @JakeLFischer.