Rings or the Max? Free Agency's Best Point Guard Can't Have Both

Kyle Lowry and DeMar DeRozan are close. Their approach to free agency is not.

When DeRozan became a free agent last summer, the behind-the-scenes buzz had him staying put with the Toronto Raptors long before he signed a five-year, $139 million deal to do just that.

The early buzz among executives around the NBA concerning his backcourt mate of the last five seasons, Kyle Lowry, has the exact opposite tone. "Toronto has been good for him, but I don't think he wants to continue living there," says one Western Conference vice president of basketball operations. "I could see him leaving."

Lowry officially made himself a free agent last week by opting out of the final year of his four-year, $48 million deal with the Raptors. While that was expected with the going rate for an All-Star point guard such as Lowry potentially being nearly three times that in today's TV-money-inflated market, he also has done nothing to quiet speculation that, at the very least, he will take a long, hard look at his options elsewhere.

DeRozan, on the other hand, told ESPN Radio at the 2016 All-Star break that it would be hard for another team to lure him away, per Marc Stein of ESPN.com. He ultimately agreed to terms with the Raptors without even allowing another team to approach him.

Reports of Lowry's interest in leaving the Raptors surfaced even before he officially became a free agent. Stein cited "late-season rumbles" in reporting Lowry was interested in a return to the Western Conference, where he spent the first six years of his career between the Memphis Grizzlies and Houston Rockets. The Philadelphia Inquirer's Keith Pompey has reported that the 76ers and Lowry also have mutual interest in joining forces. Bryan Colangelo, who was in charge of the Raptors when they acquired Lowry, took over as the Sixers president of basketball operations 13 months ago.

Bruce Yeung/Getty Images

Further fueling the Lowry-to-Philly speculation is the fact that the 11-year veteran is a Philadelphia native who went to high school there and then played two seasons at nearby Villanova. While the young Sixers are in need of experienced leadership, one Eastern Conference team's VP of personnel says he'd be leery of handing Lowry a big contract and surrounding him with lifelong friends and family.

"A guy with weight and injury issues going home would scare the hell out of me," he says.

Despite Lowry's age (31), injury history (sprained ankle and broken wrist this season alone) and tendency to gain weight outside of the calorie-burning regular season, the consensus among executives Bleacher Report spoke to at the NBA draft combine is that he and the Clippers' Chris Paul are the top two point guards on the market should Paul opt out of his contract as well. With most executives expecting Paul to re-sign with the Clippers, that leaves Lowry No. 1, followed by George Hill and Derrick Rose.

"Lowry is the best of them," says one Western Conference personnel director. "There are going to be a lot of teams interested. He's going to get a max offer, for sure."

One team executive feels the goal would be to get at least three more quality years out of him. "He's one of those guys who can get a little heavy in the offseason, but he fights and competes," the executive says.

No one, of course, can offer him more than the Raptors, thanks to the new collective bargaining agreement. Raptors president Masai Ujiri told B/R this week he is still in the postseason process of evaluating his team after the Cavaliers swept Toronto out of the second round of the Eastern Conference playoffs.

While attempting to bring Lowry back appears to be part of his master plan, Ujiri is sifting through exit interviews with players, coaches and front-office staff alike before deciding what specific changes he hopes to make for next season. The Raptors have been to the playoffs four consecutive seasons now and advanced beyond the first round in back-to-back seasons for the first time in the franchise's 22-year history, but with a veteran-laden roster, Ujiri is trying to determine if the team's core is still improving or has plateaued.

Ron Turenne/Getty Images

"Sometimes we're complacent," he says. "Now that we're good, how do we get better?"

When Ujiri told the Toronto media that the team needed "a culture reset," some interpreted that as meaning he might make significant changes or possibly even rebuild. Those close to him, though, believe whatever changes he makes this summer will be more incremental.

If he retains Lowry, and at what price, will determine just how incremental. The Raptors could give Lowry as much as $205 million over five years, while no other team can offer more than four years and roughly $152 million. Even convincing Lowry to take something less than the max would most likely mean losing three other valued free agents—Serge Ibaka, PJ Tucker and Patrick Patterson.  

What does Lowry want? That takes a bit of interpretation.

When Lowry was asked what priority would guide him on where to play next (h/t Toronto Globe and Mail), some latched onto the first part of Lowry's answer—"A ring. Nothing else. I just want a ring"—as indication that he would only consider title-contending teams. That, presumably, would knock out the Sixers or the Sacramento Kings and Dallas Mavericks, all of whom fit one of his rumored criteria (going home or going west). All, however, are also in the market for a point guard and have the cap space to offer him a max deal.

Rick Bowmer/Associated Press

But then there's the second part of Lowry's statement, which may be just as telling: that he can win a ring "anywhere I play. That's just how confident I am."

DeRozan accepted less than the max the Raptors could've offered him, but at 27 he has a chance to sign one more sizable contract. This is probably Lowry's last big deal. That, in part, is why DeRozan says their friendship will not be impacted by Lowry's decision, even if it takes him elsewhere.

"They all talk about winning and all that," says the Western Conference VP of operations. "He could tell himself that with Joel Embiid, Ben Simmons and the picks they have coming this year, they're going to contend soon enough, especially in the East. You can rationalize anything. But at the end of the day, this is his last big payday."

Ric Bucher covers the NBA for Bleacher Report. Follow him on Twitter: @RicBucher.