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The Biggest Offseason Questions for the NBA’s Second-Round Losers

Should the Clippers run it back after an all-time playoff collapse? What can the Bucks and Rockets do to get over the hump? And can Toronto afford to pay—or not pay—Fred VanVleet?

AP Images/Ringer illustration

Now that Nikola Jokic and Jamal Murray have ended the Clippers’ season, the second round of the 2020 NBA playoffs is officially in the rearview mirror. The Nuggets join the Lakers, Heat, and Celtics in the conference finals; the four teams they eliminated join all the other squads that have been ejected from Disney World like an angry dad who lost it and started swinging on the Seven Dwarfs.

The four teams headed home—the aforementioned Clippers, Rockets, Bucks, and Raptors—now enter an unprecedented offseason in which nearly everything remains in flux. As the league stitches together a new reality amid the coronavirus pandemic, we don’t yet know where the salary cap and luxury tax lines will land, when free agency will open, when the 2020-21 season will tip off, or what the collective bargaining agreement governing it all might look like. (At least we’ve got the draft date locked in!)

What we do know, though, is that our newly ousted teams all have some problems to solve—and, in most cases, considering the size of the expectations they just failed to meet, some pretty damn big ones. So let’s lend a hand and take a look at the biggest questions facing the teams whose seasons just ended, starting with an offseason champion that promised a substance-over-style identity but got drop-kicked out of the playoffs due to its lack of precisely that.

(If you’re in the market for more offseason prep, we’ve also looked at the big-ticket issues facing the eight teams that didn’t make it into the bubble, and the eight eliminated in Round 1.)


L.A. Clippers

Record: 49-23 (second in Western Conference, beat Dallas 4-2, lost to Denver 4-3)
2020 NBA draft picks: 57
Pending free agents: Montrezl Harrell, Marcus Morris Sr., Patrick Patterson, and Reggie Jackson (unrestricted); JaMychal Green (player option); Johnathan Motley (restricted)

Can the Clippers really just run it back after ... that?

It’s not just that the Clippers squandered a 3-1 lead, it’s how they did it: sprinting out to big leads in games 5, 6, and 7 before coming completely unglued on both ends of the floor. Watching a team with the NBA’s fourth-best record and third-best net rating—a team led by a two-time Finals MVP, a five-time All-NBA selection one year removed from finishing third in MVP voting, and a championship-winning head coach—suddenly turn into This Friggin’ Guy, over and over and over … I mean, it was stupefying. But it happened, and it brought about an enervating end to the first season of the Kawhi Leonard–Paul George era—which apparently wasn’t a championship-or-bust year, except that it was absolutely a championship-or-bust year, because there’s no such thing as long-range planning when you sign a short-term deal in the perpetual present tense of a title chase.

When Year 1 ends in a biblical bed-shitting, figuring out what to change so that Year 2 doesn’t end the same way becomes galactically important—especially when your two stars can both opt out after Year 2. (Worth noting: George is eligible this offseason for an extension of up to three years and just under $129 million, according to ESPN’s Bobby Marks.) But how much do Lawrence Frank and his lieutenants in the Clippers front office really want to change? And, after essentially strip-mining their asset pool in the blockbuster deal that landed George and secured Leonard’s signature, how much could they, even if they wanted to?

For all the justified criticisms of his tactical failings against Denver, head coach Doc Rivers “will be running it back next season,” sources told Yahoo’s Chris Haynes. He might have company. Morris joined midseason at the cost of a 2020 first-rounder, and he performed well, averaging a shade under 12 points and five rebounds per game in the playoffs on 51/48/93 shooting splits while posting the third-best plus-minus on the team against Denver. His combination of two-way snarl, shooting touch, and positional versatility might make him too valuable to let walk. The same goes for Green, a solid stretch big who was just the best playoff reserve on a bench featuring two Sixth Man of the Year winners, if he opts out. Harrell’s a fascinating case. He was massive during the regular season, a persistent source of chaos and interior offense who deserved the award he just won; before the bubble, he looked to be on track for a huge payday in free agency. But as an undersized 4 playing up a spot as a small-ball 5, he can also be a defensive liability on the glass and against bigger centers; in the biggest moments of the season, Jokic flame-broiled him every chance he got.


This postseason run might have dramatically slashed Harrell’s price tag, which could make it easier to bring him back. But the Clips already have nearly $116 million on the books for 2020-21. The luxury tax “apron”—the point $6 million above the projected $132.7 million tax line, the crossing of which would restrict their ability to use the midlevel exception and execute sign-and-trade deals—looms large. Will L.A. want to use all of its flexibility on frontcourt depth when what the roster lacks most is a credible point guard who’d represent an offensive upgrade over Patrick Beverley? (They could look to flip Harrell for more backcourt help in a sign-and-trade, but that’s complicated by the collective bargaining agreement’s base-year compensation rules. If his new contract increases his pay by more than 20 percent over this season, his outgoing salary in any trade would be limited to either his previous salary, which was $6 million, or 50 percent of his new salary, whichever one is higher; this would make it tougher for the Clippers to line up the contracts to get value for Harrell on his way out the door.)

I’m not sure how the Clips could present Toronto with a sign-and-trade offer enticing enough to snare Kawhi’s old buddy Fred VanVleet—or, for that matter, to land Kyle Lowry, who’s got one year and $30.5 million left on his deal. But the rejuvenated version of Goran Dragic that’s shown up in the bubble might make an interesting MLE target for a team that often seemed to suffer from the absence of a table-setter who could calm things down when they get hectic.

They’re sure as hell hectic right now, with seemingly the entire basketball-watching world coming at the Clippers’ necks. But every crisis can present an opportunity, and if Doc and the Clippers’ brass can isolate and remove the elements that sparked this season’s persistent problems, the pain of this embarrassing flameout could produce the sort of off-court growth that could pay significant dividends on the floor in big moments next season. “Chemistry is something that you’ve got to build,” ace reserve Lou Williams told reporters after Game 7. “You build it over time.” That process has to start in earnest now. With one year down and only one guaranteed year left, the Clippers don’t have a moment to lose.

Milwaukee Bucks

Record: 56-17 (first in Eastern Conference, beat Orlando 4-1, lost to Miami 4-1)
2020 NBA draft picks: 24
Pending free agents: Kyle Korver and Pat Connaughton (unrestricted); Wesley Matthews and Robin Lopez (player option); Sterling Brown, Frank Mason, and Cam Reynolds (restricted)

How can the Bucks go all in and help Giannis?

The biggest question facing the Bucks franchise—the biggest one facing the entire league, really—is whether or not Giannis Antetokounmpo will sign the five-year “supermax” contract extension that Milwaukee will present to him the second that free agency opens. He told Haynes that he won’t try to force a trade out of Milwaukee next season if the two sides don’t agree on an extension. Eric Nehm and Sam Amick of The Athletic report that the franchise has “had confidence for quite some time now that Antetokounmpo would sign the supermax.”

In the interim, if we’re working under the assumption that Antetokounmpo will be a Buck in 2020-21, then everything revolves around how Milwaukee augments a team that’s been good enough to smack the league around for two straight regular seasons, only to see the wheels come off early in the playoffs.

A few days after the Heat sent the Bucks home, Antetokounmpo met with Bucks co-owner Marc Lasry to “discuss the future of the franchise.” In that meeting, according to ESPN’s Adrian Wojnarowski, Lasry “made it clear” to Giannis that the Bucks are “willing to spend into the luxury tax to deliver him a championship supporting cast.” (That might be music to the ears of some Bucks fans; to others, it might only remind them that ownership let Malcolm Brogdon walk to Indiana last summer in a sign-and-trade deal rather than going into the tax, because, in Lasry’s words, they thought re-signing Brogdon, who’s pretty damn good, “was a luxury.”)

Another key note from Woj: Lasry, Giannis, and Giannis’s agent, Alex Saratsis, “brainstormed on some personnel upgrades that could be available to the franchise in the offseason.” Thunder guard Chris Paul quickly rose to the top of the list of potential targets for a Bucks team that desperately lacked pick-and-roll playmaking and bankable shooting in the backcourt against Miami. However, according to Nehm and Amick, “sources with knowledge of ownership’s thinking said [pursuing Paul] is highly unlikely,” given his massive price tag—$41.4 million next season, with a $44.2 million player option for 2021-22. (They also cite the “potential difficulty of bringing Paul onto a roster already led by a strong personality in Antetokounmpo,” but I’m betting any intrasquad static wouldn’t seem nearly as onerous if CP3 made the midlevel.)

You wouldn’t blame Bucks fans for being a little confused by the messaging there. If Milwaukee’s billionaire owners tell Giannis they’re willing to spend into the luxury tax to get him more help, and then signal that they won’t pursue what could be a perfect fit because it’s going to cost too much, then it sounds like we’re still haggling over price. So how much will they be willing to spend, and who can you get for it?

If the Bucks aren’t looking to pony up for Paul, you’d imagine they’d also be out on Russell Westbrook, who makes even more, and who might not solve their current Eric Bledsoe problem as much as he’d put a different spin on it. If Milwaukee was really going all in, and was willing to take a big swing in that salary tier, I’d be kind of intrigued by the idea of taking a run at a reportedly healthy John Wall. I know: There’s the Achilles injuries, and the similarly shaky shooting, and the $132.9 million still coming his way. But an ambulatory and operational Wall would represent a marked improvement over Bledsoe as a shot creator and pick-and-roll facilitator; he has also performed more consistently in the playoffs than his former Kentucky teammate.

Lowry makes sense as a target on paper, as a similarly styled and similarly productive player to Paul on a cheaper deal. But that would require Toronto deciding to move Lowry rather than just keeping the franchise legend. And if it did, it would be unlikely to send him to a conference rival that it also might be competing against in free agency for Giannis next offseason. Mike Conley checks a lot of the same boxes, but Tony Jones of The Athletic reported both that Conley is “very, very likely to opt into the final season of his contract” and that the Jazz “will likely bring the entirety of [their] core back for a second run next season.”

I don’t think either Milwaukee or Portland would pitch this idea, but something built around CJ McCollum for Khris Middleton feels like it could be an interesting roster-balancing shake-up for both sides. The Pelicans would likely listen to a Jrue Holiday offer, but they’re probably going to be fielding a few of those, and I’m not sure Milwaukee’s got the goods to win that race. DeMar DeRozan seems very gettable, and would walk into Wisconsin as the team’s best late-game shot creator and pick-and-roll playmaker, but he doesn’t solve the shooting problem, and also he might be a power forward now?

The longer you look at it, the fewer clear-cut difference-makers you see the Bucks having a real shot at getting. That doesn’t mean they won’t succeed; the grim prospect of Giannis leaving demands the front office leave no stone unturned in pursuit of more and better-suited talent. (Except, it seems, on the sideline.) It does mean, though, that if they get a crack at one, ownership has to open up the wallet and pay what it takes. Failing to do so might save some money now. But it could cost them everything down the line.

Toronto Raptors

Record: 53-19 (second in Eastern Conference, beat Brooklyn 4-0, lost to Boston 4-3)
2020 NBA draft picks: 29, 59
Pending free agents: Fred VanVleet, Marc Gasol, Serge Ibaka, and Rondae Hollis-Jefferson (unrestricted); Stanley Johnson (player option); Chris Boucher, Malcolm Miller, and Oshae Brissett (restricted)

How far are you willing to go to keep VanVleet?

The origin story traces back to the summer of 2016, when VanVleet—a two-time Missouri Valley Conference Player of the Year at Wichita State, but an undersized prospect from a mid-major—passed on multiple chances to be drafted in the second round in favor of going undrafted and trying to earn a guaranteed deal. The risk paid off: After he played well in summer league, Toronto rewarded him with a two-year deal. Playing well with Raptors 905 in the G League earned him a rotation role in his second season; playing well in that role earned him a two-year, $18 million deal in restricted free agency in 2018. At every step, VanVleet has bet on himself—it’s literally his brand—and reaped the rewards.

So, too, have the Raptors, who have watched VanVleet develop from a central-casting Lowry understudy to a Finals folk hero to a bona fide starter who averaged a shade under 18 points and seven assists per game and can defend both backcourt positions at a near-All-NBA level. But with VanVleet hitting an unrestricted market in which several teams with significant cap space—the Knicks, Pistons, and Suns, reportedly—are interested in exactly what he brings to the table, will Toronto be willing to double down on its investment and pay VanVleet what he’s worth … even if it means compromising its ability to retain the financial flexibility to make a franchise-altering addition in 2021?

As The Athletic’s Blake Murphy dutifully detailed, it’s possible to do both, depending on where the cap lands in a post-pandemic environment. They could retain VanVleet on a roughly market-rate four-year deal and still maintain a Giannis Antetokounmpo–size max salary slot (or, you know, whoever, just making conversation!) for 2021. It’s a narrow needle for Masai Ujiri—who might be up for a new deal himself—to thread, and it will require carefully navigating rookie-scale extension talks with linchpin wing OG Anunoby, and it will probably mean saying goodbye to Norman Powell, but it’s (theoretically) possible. Every additional dollar that New York, Detroit, Phoenix, or someone else tacks onto its offer further complicates that math, though. If a suitor’s willing to offer VanVleet a starting salary higher than the total value of his last deal, suddenly the Raptors will have to find other, and potentially more painful, places to tighten their belts.

It may well be worth it. VanVleet’s awesome and, at 26, is just entering his prime; pairing him with Pascal Siakam (whose offseason development following a rough bubble run promises to be a major story line) and an extended Anunoby would lock in a talented, tough, and versatile young core that you can sell to rainmaking free agents. Better to pay now to secure the talent and figure out the math later, and all that. The one certainty: resolving this situation’s going to require a lot of math. After years of betting on himself, Steady Freddy’s about to cash in. The only question now is whether the Raptors want to be the ones paying up.

Houston Rockets

Record: 44-28 (fourth in Western Conference, beat Oklahoma City 4-3, lost to the Lakers 4-1)
2020 NBA draft picks: None
Pending free agents: Jeff Green, Tyson Chandler, Thabo Sefolosha, DeMarre Carroll, and Bruno Caboclo (unrestricted); Austin Rivers (player option); David Nwaba (team option); Michael Frazier and William Howard (restricted)

Can a new coach get more out of the Harden-Westbrook core?

I doubt neither Daryl Morey’s ingenuity nor his commitment to exploring every possible avenue to do something that might raise the Rockets’ ceiling. It’s just that, after years and years of arbitrage that have turned one red paperclip into Levitated Mass, I’m not sure how many moves there are for Morey to make that meaningfully nudge Houston’s needle north.

James Harden, Russell Westbrook, and Eric Gordon will combine to make $99.5 million next season. That takes up about 91 percent of Houston’s space under the projected $109.1 million salary cap; guaranteed deals for vital forwards Robert Covington and P.J. Tucker, and for the suddenly infamous Danuel House, take up the rest. That’s six dudes. If Rivers picks up his player option, that’d give the Rockets less than $7 million under the luxury tax line—which owner Tilman Fertitta has been famously squirrelly about crossing—plus the $9.3 million midlevel and $3.6 million biannual exception to not only fill out the rest of the roster, but improve upon it, considering this year’s model once again sputtered out in the second round.

They could try to flip Gordon, though how much value they’d get for an about-to-be-32-year-old with a lengthy injury history is a big question. They could dangle Tucker’s expiring deal for help, but then they’d have to replace everything he brings to a small-ball scheme that will evidently remain in place even after Mike D’Antoni’s exit, and do it on the cheap—good luck there. They don’t have any 2020 draft picks to include in a deal, after sending out their first-rounder for Covington in February and their second-rounder for Iman Shumpert in 2019. They can move a 2021 or 2022 no. 1, but Sam Presti owns all of the rights beyond that.

Maybe Morey triples down and finds an all-in swap of Westbrook for one or more of the league’s other most onerous contracts—I’m not sure there’s enough Zoloft on the market for all parties involved to start discussing Russ-for–Tobias Harris frameworks—or damns the torpedoes with a “fuck everything, we’re doing five blades” decision to seriously consider life after Harden for the first time. Barring those unlikely events, though, we’re probably talking about Houston working to unearth the next crop of Houses, McLemores, and Greens, and hoping that Morey can find a new coach who can coax more out of the incumbent stars than D’Antoni did.

Maybe that’s a hard-ass type; Jeff Van Gundy and Kenny Atkinson come to mind. Maybe that’s someone who played in the league, has a championship pedigree, and a reputation for being straight with players; Tyronn Lue and Sam Cassell make a ton of sense. Maybe Morey, who praised D’Antoni for his willingness to innovate and push the Rockets’ idiosyncratic construction to the extreme, looks for even more zealous ideological alignment: ESPN’s Tim MacMahon highlights Chris Finch—whose globetrotting coaching résumé includes stints in the Rockets’ G League laboratory in Rio Grande Valley and on the Houston bench, and who most recently served as the associate head coach in New Orleans under former D’Antoni assistant Alvin Gentry—as a “name to watch,” noting that “a mindset similar to Morey’s is a must for a Rockets coach.”

That makes sense; you need everyone rowing in the same direction to get where you want to go. But after repeatedly being the same kind of different and coming up short, you wonder whether a different kind of different might be the prescription for what seems to persistently ail these Rockets.