NBA Insider Tom Haberstroh

NBA Insider Tom Haberstroh

It took five postseasons without a title before Masai Ujiri had seen enough. 

With Kyle Lowry and DeMar DeRozan anchoring the backcourt, the Toronto Raptors had seemingly tapped out. In five seasons from 2013-14 to 2017-18, the Raptors won more regular-season games than any other Eastern Conference team, but the Raptors saw more first-round exits than trips to the Eastern Conference finals, never reaching the NBA Finals.

And so, last July, Ujiri made his move. The Raptors traded DeRozan -- the leading scorer in franchise history at the peak of his career -- along with Jakob Poeltl and a top-20 protected 2019 first-round pick to the San Antonio Spurs for Kawhi Leonard, Danny Green and cash considerations. The Lowry-DeRozan backcourt was broken up, the Coach of the Year Dwane Casey was let go after seven seasons, and a new era in Toronto had begun.

The results have, so far, been positive. Despite Leonard missing about a quarter of the season, the Raptors currently have better championship odds than they did at this time last year. As such, Ujiri’s home run swing effectively put the rest of the league on notice. If DeRozan isn’t safe, who is? Just like Miami’s Big Three sparked the era of player agency, the Raptors could have broken the seal for other perennial underachievers to follow suit.

Here are “this is it” teams who could be due for a shake-up of the status quo:


Boston Celtics

Who would have thought they’d find themselves on this list back in September? Not many. League executives can’t agree on much, but there’s a general consensus that this Celtics team could look very different come next season, especially if they get bounced early in the playoffs. 

Danny Ainge is not one to prioritize emotional sentiment over cold rationality. Ask Isaiah Thomas. If Ainge feels like the team is better off without Kyrie Irving, they’ll have a Plan B in place to move on from the All-Star, should Irving leave as a free agent this summer.

Irving hasn’t been the most galvanizing leader. Some outsiders believe that his lukewarm approval rating in the locker room might give the Celtics some pause before handing over a long-term max deal. Said one league executive of Irving: “You’re offering that guy back on a humongous deal? That’ll be interesting to see.”

The Celtics are 11-3 this season without Irving in uniform and were one game away from reaching the NBA Finals without him last postseason. It’s tempting to think there’s some Ewing Theory at work here, that the Celtics are actually a superior team without Irving. But that 11-3 record is misleading once you account for the lopsided schedule. The Kyrie-less Celtics are 2-1 against teams currently with winning records and 9-2 against everyone else, including three wins over the hapless Cavs. That’s far less convincing. Watch the 2016 Finals if you need a reminder about Irving’s power in the playoffs.

The interesting thing from the Celtics’ perspective is that Irving is seen as something of a package deal with Anthony Davis. If Irving stays, the Celtics could shoot up to the top of the Davis sweepstakes in New Orleans due to their appealing collection of young talent and draft assets. The Celtics might be more willing to part with their prized youngsters if they can flaunt an Irving-Davis partnership and rule the East. If Irving leaves, though, the Celtics might continue with Gordon Hayward, Jayson Tatum and Jaylen Brown as the faces of the franchise. 

Few teams have had their long-term assets sour more than the Celtics’ this season. Tatum and Brown haven’t taken the leaps expected of them, respectively. Their 2019 Sacramento first-round pick almost assuredly won’t be in the top-10. The Clippers went on a tear, meaning their 2019 pick owed to the Celtics is less valuable than Boston’s own first-round pick. On the other hand, Memphis’ top-eight protected pick is likely to roll over to next season, making it top-six protected in 2020 and fully unprotected in 2021. That could be a extra tasty pick in 2021 if the age limit is lowered to 18 years old by then.

If the Celtics disappoint this postseason, they could be in for a reshuffling, a la the Raptors. But  if the Celtics reach the Finals, it’s hard to imagine Irving leaving, especially when Davis is on the trade block. Then again, if he really is listening to LeBron James’ wisdom, reaching the Finals in 2014 didn’t exactly seal the deal for James to stay in Miami.


Portland Trail Blazers

This is Raptors West. Since C.J. McCollum became the full-time starter next to Damian Lillard in 2015-16, the Blazers’ backcourt has won the second-most games in the NBA (161), only trailing the Stephen Curry and Klay Thompson (219) among starting backcourts. The Lowry-DeRozan tandem comes in third at 140, which still ranks high despite not even playing together this season. That’s how rare these consistent backcourts are.

Like the Raptors, the Lillard-McCollum duo has also come up short in the playoffs, going 5-14 in the past three postseasons, including two disheartening first-round sweeps. A Portland supporter might argue that two of those postseason exits came at the hands of perhaps the most unbeatable team in NBA history -- the Golden State Warriors. But the Raptors had an excuse, too: they ran into LeBron James in three straight postseasons. Ujiri still decided to make a change.

If the Blazers disappoint again, is the Lillard-McCollum partnership due for a backcourt breakup a la Toronto? 

Don’t bet on it. If anything, the Jusuf Nurkic injury probably delays any potential shakeup. It might also buy some more time for Terry Stotts, who is reportedly under contract only through next season.

But there is at least some uncertainty here after longtime owner Paul Allen died in October, putting a possible sale on the horizon. Though unlikely, a tightening of the belt could be in store for a team that paid the luxury tax this season and is right up against the luxury tax line in 2019-20. 

It’s a surprising plane of existence for a small-market team like Portland. The Blazers have ranked among the five-highest payrolls in the league in each season since the 2016 spending spree that saw them ink Evan Turner, Allen Crabbe, Meyers Leonard and Mo Harkless to deals that totaled over $225 million. But a potential cost-saving teardown probably wouldn’t come this offseason. The Blazers are still competing at a high level and generating playoff revenue, even if it’s only been a couple home games the last two postseasons.

Said one rival league executive: “As they’re built, is it championship-caliber? No. But they’re fighting for a top-four seed every year. In a small market, that, in some ways, is good enough.”

Lillard could be eligible for the four-year, $194 million supermax extension this summer if he lands on the All-NBA team, which is basically a lock. Averaging a torrid 25.9 points, 9.6 assists and 5.1 rebounds since McCollum got injured last month, Lillard ranks second among all guards in total win shares and RPM wins this season. He is the gold standard of durability, having played more games than any guard since he entered the league in 2012-13. He deserves every penny that the collective bargaining agreement allows.


The late Paul Allen would almost certainly be willing to commit that money to the face of the franchise, and it’s likely his successor would, too. A professional like Lillard is hard to come by and he’s said all the right things about being a Portland lifer. Most around the league don’t see him jumping ship from a small market like James in 2010 or Kevin Durant in 2016.

“[Lillard] is more likely a Dirk thing,” said one West executive. “He’s more likely to stay there and hopefully they get one title one day. If you hang on and get one [in Portland] eventually, as opposed to asking out, it’s more valuable than the three (titles) that KD got.”

Lillard and McCollum are under contract through 2020-21. If Allen was still steering the Blazers, there wouldn’t be any chatter about breaking it up. But with question marks lingering around ownership and the trickle-down effects of a potential new regime, there’s a bit of unsteady ground here, enough for power-brokers in the league to keep tabs on. 

Toronto Raptors

Again. Most executives think Kawhi Leonard has one foot in Canada and one in ClipperLand. At least that’s the buzz from the NCAA tournament. One plugged-in executive told me that Leonard’s preference is so strong that barring an unlikely title run for the Raptors, “the Clippers believe they have it in the bag.”

Of course, few around the NBA expected Paul George to re-up with OKC, but that might be the exception, not the rule. The Raptors could be retooling again if the Leonard experiment falls flat. Both Leonard and Marc Gasol could walk away by turning down their 2019-20 player options and go into free agency. If that happens, the Kyle Lowry era could also be over one year after Toronto cut ties with DeRozan.

It won’t be an easy contract to unload. Lowry is due $33.5 million next season and turns 34 years old next March. (Would Memphis take on Lowry’s expiring deal (a Beale Street reunion!) to swap with Conley’s remaining two years at a similar number?) Many around the league expect the Raptors to hit the restart button and build around Pascal Siakam, who has emerged as a star in the making. For those who doubt Siakam’s starpower check this: In the last 10 games that Leonard hasn’t played, the 24-year-old Siakam has averaged 22.9 points, 8.3 rebounds and 3.6 assists on 54.3 percent shooting from the floor and 39.5 percent from downtown. There are no Kawhi proxies in the NBA, but that’s as close as you’re going to get.

Like Boston, the Raptors could look a lot different next season if things don’t go their way. Danny Green, who might be the best role player in the NBA, can be a free agent and will likely generate a hefty pay-raise from his annual $10 million he signed in 2015 with the Spurs. There’s a realistic scenario where the Raptors punt on their six-year title pursuit and build around their youngsters with an eye for the top of the draft. Siakam, OG Anunoby, Norman Powell and Fred VanVleet are a solid foundation and none of them were lottery picks. What if they get some swings at the top of the draft? That day might come sooner than many think.


The Others

It may not be a make-or-break postseason for Golden State, Philadelphia or Indiana, but each of these teams could look very different next season regardless. If the Warriors win the title, many executives believe that Durant may be more included to leave. It’d tie a bow on a powerful narrative of Durant as the Warriors’ savior.

They lose to Cleveland without him. Durant comes to the rescue and voila, they three-peat. He’s the alpha. The reason they overcame LeBron James. End of story.

If the Warriors are somehow knocked out before claiming their third title in four years, it’s expected that Durant could still leave anyway. Klay Thompson is also a free agent this summer, but there's no buzz that he's going to leave, regardless of what happens this postseason.

As for Philadelphia's long-term prospects, a deep playoff run matters to a degree but don't expect a blow-it-up scenario where they punt on the Joel Embiid-and-Ben Simmons partnership. Tobias Harris, J.J. Redick and Jimmy Butler -- all can be free agents -- will be expensive to retain, if they want to come back. But the Sixers aren't primed to break up Embiid and Simmons like the Raptors did with Lowry and DeRozan. Elsewhere at the top of the East, six of Indiana's rotation players, including Bojan Bogdanovic, who is averaging 22.0 points per game since the All-Star break, will be unrestricted free agents. But the young core of Victor Oladipo, Myles Turner and Domantas Sabonis should still be in place.

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