As the Raptors go extinct, another tricky offseason looms large

CLEVELAND, OH - MAY 7: DeMar DeRozan #10 of the Toronto Raptors reacts during the second half of Game 4 of the second round of the Eastern Conference playoffs against the Cleveland Cavaliers at Quicken Loans Arena on May 7, 2018 in Cleveland, Ohio. The Cavaliers defeated the Raptors 128-93. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Jason Miller/Getty Images)
CLEVELAND, OH - MAY 7: DeMar DeRozan #10 of the Toronto Raptors reacts during the second half of Game 4 of the second round of the Eastern Conference playoffs against the Cleveland Cavaliers at Quicken Loans Arena on May 7, 2018 in Cleveland, Ohio. The Cavaliers defeated the Raptors 128-93. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Jason Miller/Getty Images) /

After a transformative 59-win regular season, the Toronto Raptors have once again woken up on Groundhog Day. The Raptors have gotten swept by Cleveland Cavaliers again. Remarkably each loss has somehow been more gutting than the last, as Toronto has created new ways to self-destruct. The Cavs shot 59.5 percent in the Game 4 closeout, undressing the Raptors 128-93. LeBron has essentially trolled this team into oblivion. His preposterous running floater off the glass to seal Game 3 at the buzzer was the culminating act in the litany of torments he’s inflicted upon Toronto:

That play basically sums up the series. What a heart-wrenching end to an exciting season for Toronto.

When the NBA Playoffs began, this Raptors team looked stylistically different than many of its past iterations. Perhaps this bunch, with a new offense, a killer bench and an improved DeMar DeRozan could finally dethrone LeBron and the Cavaliers in the East. Nope. It’s just wasn’t going to happen. Suggesting that Toronto’s season was an abject failure because of their destruction at the hands of LeBron however would obviously be reductive.  The habits the team has built, the chemistry it exhibited and the growth of so many pieces on the roster really matter. The offensive system that Coach Dwane Casey and his staff put into place matters.

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The development of the young players on the Raptors is an especially important factor that we shouldn’t overlook when evaluating Toronto’s season. Stealing OG Anunoby late in the 2017 Draft was huge for this team. He’s a strong defensive presence on the wing that every team needs in order to slow down unstoppable forces like LeBron, KD, Giannis and Kawhi on a nightly basis. Fred VanVleet, Paskal Siakam, Jakob Poeltl and Delon Wright all played big roles for a 59-win one-seed. That matters.

But in the world of the NBA, the results always matter too. This year’s matchup with Cleveland was Toronto’s best shot to finally knock out its playoff bogeyman. The Cavs got weaker, the Raptors unexpectedly got better and yet Toronto still came up miles short. That’s the cold, demoralizing truth. This was a full on firebombing and somebody will have to take the fall for it.


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At this point, General Manager Masai Ujiri and the Toronto front office will have to start asking themselves some tough questions that are all too familiar. Is this a core that can viably contend for the NBA championship in the future? If the answer to that question is no (and boy does it seem to be a resounding no), what changes will the franchise make going forward? Will they fire Coach Casey? Will they trade Kyle or DeMar… or perhaps even both? These are hard questions for a 59-win team and the answers to them are unclear, especially because the league’s power balance will be so uncertain until free agency settles down in mid-July.

Since the 2016 offseason, in which DeRozan entered unrestricted free agency, the Raptors have kept their core intact despite demoralizing playoff losses to the Cavs. Over the past few seasons, Toronto has added valuable role players around the Lowry and DeRozan duo. Management successfully constructed a deep, versatile roster. But matters are  going to get trickier this summer.  Toronto will face serious luxury tax issues over the next few years. With Norman Powell’s extension kicking in at the start of the league year, the Raptors will vault into tax territory by July.

Furthermore, the big money deals of Kyle Lowry and Serge Ibaka expire after the 2019-2020 season and Jonas Valanciunas has a player option for that same year. Given the reduced market value of post brute big men, Jonas will almost certainly pick up that option. And lastly, Fred VanVleet will hit restricted free agency this summer. Is ownership willing to pay a fortune for a team that hasn’t displayed true championship pedigree? Or will cost cutting moves be a top priority? We will find out very soon.

The path forward is going to be difficult for this team. Discussions surrounding the future prospects of teams like the Raptors (languishing fringe contenders and pseudo-contenders) often outline only two courses of action for such teams. They can either take an extreme approach by tearing down the roster and completely rebuilding, or they act conservatively by keeping the current core intact and pursuing peripheral changes. The latter option would probably entail bringing in a new coaching staff and trying to obtain a legit third option on the roster for example.

But I think there is a legitimate middle path for these teams that are seemingly stuck. They can utilize elements of both strategies without totally committing to one approach. That’s obviously a tricky dance to pull off, but Toronto can do it.  The Los Angeles Clippers, a team that the Raptors have drawn comparisons to in the past, followed such a path last season. Though it seems like an eternity ago, Los Angeles got off to a scorching start in November 2016 and for about 20 games seemed like the second best team in the West. The wheels slowly came off and they eventually flamed out against the gritty Utah Jazz in a Game 7 loss at home.  After another brutal playoff loss and more crappy injury luck, it became painfully clear that Griffin-Paul Clippers were never going to win the championship or even make the Finals.

Since June 2017, the Clippers have undergone more of a controlled demolition than a complete roster blow up. They’ve essentially remodeled on the fly. Los Angeles traded Chris Paul for a nice mix of veterans and young fringe guys. They then centered the roster around Blake Griffin, re-signing him to a monstrous five-year contract worth $171 million. Management then tested the waters for a few months with a wacky Blake-centric team that hovered around the bottom of the West playoff race.

When the opportunity arose Los Angeles pivoted once more, jettisoning Blake Griffin and receiving Tobias Harris, Avery Bradley, Boban Marjanovic and a 2018 first-rounder in return. In making that deal the Clippers gained a financial maneuverability moving forward; their books aren’t clogged by one of the league’s riskiest contracts and they received a number of solid assets in return. Right now, the Gallinari contract is the only deal on Los Angeles’ cap sheet that stands out as somewhat ugly. They are no longer damned to salary cap purgatory.

Of course, we don’t yet know the results all these moves will have moving forward. There is no guarantee that the Clippers will land a big star via free agency or trade this summer. And they are still very much the little brother to the Lakers in the Los Angeles market. If they come up empty-handed they could be stuck on the outside of the playoff picture instead of being a perennial playoff team as they were in the Lob City days.

But having acknowledged those risks, I think that the Clippers are in a much brighter spot now than they were at this time last year with a creaky, aging core. The 2018 Clippers became a unique, entertaining team with none of the bad juju of the Lob City bunch. Although they missed the playoffs, they have now positioned themselves to realistically pursue big time free agents. And if the Spurs ever launch a Kawhi Leonard trade sweepstakes, the Clippers have a few decent trade chips to throw San Antonio’s way.

The 2018 Raptors have an eerily similar vibe to the 2017 Clippers. Many of us briefly talked ourselves into them as contenders, only to see them fall apart in the same depressing fashion that they had countless times before. In both cases, constant playoff misery has exposed the unviability of the core as a championship cornerstone. An air of hopelessness seemed to permeate every facet of these teams during their playoff runs. When things started to go wrong, self-destruction always loomed around the corner.

Perhaps the best way forward for Toronto is to follow the example of the Clippers. We’ve seen the Raptors take a fairly cautious approach in the recent past, staying the course and keeping its core together. The time has come for more substantive change. That doesn’t mean that the Raptors should burn this team to the ground of course. Toronto has the assets and the players to pivot in a major way without firing up the tank and launching a grueling rebuild. Moreover, Masai Ujiri is a bold GM. He won’t be afraid about shifting this franchise into a new era.

In terms of roster reconstruction management’s first order of business should be to unload as much bad salary as they can, as soon as they can. Trading two of the Lowry, Ibaka, Valanciunas triptych would be ideal. The front office should leave every option on the table here though. If teams come calling for DeRozan, Toronto should listen. He would theoretically be easier to trade than Lowry. If possible, the Raptors could try to flip either Lowry or DeRozan for a younger asset that will be less costly long term or a nice draft pick. They could refocus the roster around their remaining All-NBA guard, comfortably duck the tax and play things out until the deadline.

The Raptors have numerous young players that can step up and take on bigger roles. The team would take a sizable step back next season in order to gain some flexibility moving forward. But Toronto’s reliance on the likes of Siakam, VanVleet, Poeltl, Wright and OG in 2018 bodes well for the future. The fact that we’ve seen the young  guys play at a high level would make such a transition far more palatable. A new-look Raptors squad would not be some unwatchable 25-win team that plays an ugly style of basketball. Ball movement and egalitarian offense were staples of Toronto’s bench units this year and we could reasonably expect such an approach if those dudes received more playing time.

Moving on from some combo of Ibaka, Jonas, DeRozan or Lowry would be hard, emotionally and logistically.  DeRozan and Jonas have played their whole careers for the Raptors. Lowry has grown immeasurably as a player in Toronto, blossoming late in his career and finding a real home after bouncing around the NBA for a few years. They have all meant so much to this era of Toronto basketball. From a logistical perspective, constructing workable trades involving these guys will also be tricky.

The Jonas and Ibaka contracts will be extremely difficult to move; if Toronto finds reasonable deals for either guy it should pull the trigger immediately. Players of Valanciunas’ ilk simply aren’t in high demand. Making about $17 million annually Jonas is on a deal that’s not a total disaster, but it’s certainly rough. The Lakers had to include D’Angelo Russell in their salary dump of Timo Mozgov last year. Valanciunas is of course a much better player than Mozgov, but the point still stands. Moving on from these types of players bears a steep asking price.  Toronto might just have to stomach the Jonas contract, which they’ve unsuccessfully tried to deal in the past.

The current value of Ibaka is far more concerning. In what has seemingly become a playoff tradition, Ibaka looks like a shell of his former self. He’s not the defender he once was and on offense he always seems to be a beat too slow. Serge’s value is probably at an all-time nadir after these playoffs. He shot 42 percent percent from the field through two playoff rounds and he will make about $45 million over the next two years. Yikes. That’s far too much for player that’s clearly on the downswing. The Raptors won’t be able to move on from him without attaching a future asset or taking back a rough contract in return.

The dynamic backcourt duo of Lowry and DeRozan will be in higher demand than Toronto’s bigs of course. Although, Lowry is 32 and set to make nearly $65 million through 2020. But he was also an All-NBA guard not long ago and after a rough start to this season he got back into form as the year progressed. If the injury plagued Blake Griffin was traded for a king’s ransom, would it be impossible for a desperate team to overvalue Lowry? I think not. As noted above, DeRozan would be easier to trade than Lowry. He’s turning 29 in August and he’s on one of the few summer 2016 contracts that wasn’t a catastrophe.

But who could the Raptors realistically acquire for these guys that would fit well with their style of play? Perhaps they could ship DeRozan to Miami for a package centered around Justise Winslow. That might not be especially compelling, but Winslow is the type of player that’s worth targeting in these deals: a highly touted lottery guy with a few clear talents that hasn’t developed according to schedule. Miami has longed for a star for the past few years, maybe they could talk themselves into a DeRozan trade.

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A player that the Toronto fan base might be more receptive to is Andrew Wiggins. Trade rumors have swirled around the former top overall pick and Toronto native for months now. A swap including either Lowry or DeRozan could work theoretically, but Minnesota would be taking a pretty big risk in either case. Lowry is 32 and small point guards don’t have a track record of aging well.  Meanwhile, a DeRozan-Butler wing combo would present many of the same fit issues that currently exist for the Wolves.  A Toronto team with Wiggins could have fit issues of its own, but he at least fits the bill as an underachieving guy with a high ceiling. If Toronto could actually land Wiggins (though his contract does look a bit scary right now) there’s a chance he could thrive in an offensive environment with better spacing and movement.

In any case, the Raptors should be proactive. We’ve seen teams wait too long to make changes before. The results can be disastrous. That’s a bitter pill to swallow coming off the best regular season performance in franchise history. But after seeing the Cavaliers batter the Raptors again, I’m not sure that bringing back the roster or coaching staff as presently constituted is a good idea. Again there are no guarantees here. The Raptors might not win 59 games again any time soon. But the air of hopelessness has to go. The comical inevitability of the playoff collapses has to go. This version of the Raptors has officially run its course. It’s time for some new blood to go North.