Five Key Offseason Questions

Five Key Offseason Questions: Toronto Raptors

The Raptors‘ decision to part ways with Coach of the Year Dwane Casey and then to trade beloved star DeMar DeRozan generated some angst among the fanbase last summer. But the moves ultimately paid off in dividends for the long-snakebitten organization this spring.

A Raptors postseason run that featured an improbable Game 7 buzzer beater against the Sixers and a comeback from a 2-0 deficit against the Bucks culminated with a Finals win over the Warriors for Toronto’s first NBA championship. Now, with the hangover from that title celebration still wearing off, the club will have to figure out whether it can keep All-NBA forward Kawhi Leonard and make another run in 2019/20.

Here are five key questions facing the franchise this summer:

1. Will Kawhi Leonard re-sign?

With Kevin Durant expected to miss the 2019/20 season due to his torn Achilles, Leonard is unquestionably the top free agent on the market. And with just hours remaining until free agency officially begins, we still don’t really have a sense of what his plans are.

Did his championship run with the Raptors make him gain a new appreciation for Toronto or does he still want to play in his hometown of Los Angeles? Would teaming up with LeBron James and Anthony Davis on the Lakers appeal to him after he led a team to a championship as the unquestioned No. 1 option? Does he want to join forces with another top free agent like Durant or Jimmy Butler? Does he intend to sign a shorter-term deal or opt for long-term security?

All of these questions remain up in the air, which makes it impossible to get a good read on how likely a return to Toronto is. That puts the Raptors in a tough situation, especially if Leonard doesn’t intend to make a quick decision once free agency opens, since their outlook going forward hinges on whether they’ll have the Finals MVP for five years, two years, or one year — or not at all.

Fortunately for the Raptors, they’re not in a position where they’d have to remain in a holding pattern with other top free agents as they wait for Leonard’s decision. They don’t project to have cap room, so Kawhi’s decision may actually not impact their 2019 offseason roster moves in a huge way. Most of their key contributors remain under contract.

It’s possible Danny Green‘s free agency decision will be tied to Kawhi’s to some extent, and the Raptors may not be limited to just the taxpayer mid-level exception if Leonard heads elswhere Otherwise, I wouldn’t expect their short-term plans to change too drastically based on Kawhi’s decision.

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Five Key Offseason Questions: Golden State Warriors

After a fortunate run of good health during the previous four seasons, the Warriors suffered back-to-back devastating injuries during their fifth consecutive NBA Finals appearance, as Kevin Durant ruptured his Achilles in Game 5 vs. Toronto and Klay Thompson tore his ACL in Game 6.

The injuries raise questions about the Warriors’ ceiling for the 2019/20 season, but with a move to San Francisco on tap and a healthy Stephen Curry and Draymond Green still leading the way, one thing is clear: Golden State’s management has no intentions of taking a step back and retooling its roster.

Here are five key questions facing the franchise this summer:

1. Will Kevin Durant re-sign with the Warriors?

Klay Thompson was never viewed as a serious threat to sign with any team besides the Warriors, and a Saturday report indicated that he’s planning to agree to terms with Golden State on a five-year, maximum-salary offer shortly after free agency begins. That leaves Durant as the Warriors’ primary concern.

Durant will also be eligible for that five-year max. In fact, because of his additional years of NBA experience, a five-year deal for KD would be worth about $31MM more than it Thompson’s own five-year deal — Durant’s maximum salary is worth over $221MM, while Klay’s falls just shy of $190MM.

Although he has opted for shorter-term contracts since arriving in the Bay Area, the time is right for Durant to shift his focus to long-term security. Because the Warriors now have his full Bird rights, he’s eligible for the first time to sign a five-year contract with the club — and that should look more appealing than ever after the injury he suffered in the Finals.

With no assurances that he’ll ever get back to being the same player he was before tearing his Achilles, Durant can’t count on a future contract to make up the $57MM he’d forfeit by signing a four-year, $164MM deal with another team.

Still, we don’t know exactly what Durant’s thinking heading into free agency. Is that extra year (and that $57MM) a significant factor for him? Is he upset at all about the way the Warriors handled his calf injury in the postseason? Did suffering that Achilles injury in Game 5 after pushing to make it back to the court bring him closer to his Warriors teammates?

I think a reunion with the Warriors is still a possibility, though I’m not sure it’s the most likely scenario at this point. We’ll find it in a matter of days what Durant is thinking.

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Five Key Offseason Questions: Portland Trail Blazers

After suffering an embarrassing first-round sweep at the hands of the Pelicans in 2018, the Trail Blazers weren’t even considered a lock to make the postseason in 2019. During the preseason, oddsmakers pegged Portland’s over/under at 42.5 wins, ninth in the Western Conference.

The Blazers easily exceeded that total, finishing with a 53-29 mark and claiming the No. 3 seed in the West. Although their season ended once again with a four-game sweep, it happened in the Conference Finals this time around, after they’d eliminated the Thunder with a memorable Damian Lillard buzzer beater and knocked off the Nuggets in a Game 7 in Denver. Portland will enter the 2019/20 season looking to build on that playoff success.

Here are five key questions facing the franchise this summer:

1. How close are the Trail Blazers to legit title contention?

The Trail Blazers didn’t win a single game against the Warriors in the Western Finals, but they built double-digit leads in each of the last three contests and led for most of those games. Now that Golden State will be without Kevin Durant and Klay Thompson for most or all of next season, do the Blazers have an opening to win the West?

Well, yes and no. Portland’s path to the Western Finals was a favorable one, as the team avoided what would have difficult matchups against the Rockets or Jazz. If the bracket had looked a little different, it’s entirely possible that the Blazers could have been eliminated a round or two earlier.

But the West should be more wide open in 2019/20 than it has been in years, so there’s reason for the Blazers to believe they’re just one or two moves away from breaking through. The Raptors, who could have been considered the Blazers of the East in recent years, are a good reference point for Portland — Toronto suffered several postseason disappointments and repeatedly fell short of the NBA Finals before winning a championship in 2019. Maybe the Blazers could follow suit.

Unlike the Raptors, who had to break up their All-Star backcourt to take that next step, I don’t expect the Blazers to seriously consider moving Lillard or CJ McCollum. Instead, it makes more sense for Portland to try to acquire a third impact player using their growing collection of assets. Kevin Love has been a frequent subject of speculation as that impact player, though I expect the Blazers to aim even higher.

There aren’t likely to be teams pushing hard to pry Love from the Cavaliers this summer, and the Blazers could afford to wait until the 2020 trade deadline to try to make a splash if they don’t find a deal they like this offseason, so Love is an option that could be circled back to down the road.

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Five Key Offseason Questions: Milwaukee Bucks

The Bucks broke out in a big way in 2018/19, rebounding from a disappointing 2017/18 season to win an NBA-high 60 regular-season games and two playoff series before falling just short of the NBA Finals. A deep, talented roster put together by Executive of the Year Jon Horst was led expertly by Coach of the Year Mike Budenholzer and MVP Giannis Antetokounmpo.

The Bucks’ core players are young enough to build on this year’s results and improve upon them without major roster changes, but before that can happen, the team will need to address several contract situations. Of Milwaukee’s eight most-used players in the postseason, four are free agents and another is a strong candidate to be released due to an unwieldy contract.

Here are five key questions facing the franchise this summer:

1. Will Khris Middleton be re-signed?

The answer to this question appears to be a resounding yes. When ESPN’s Adrian Wojnarowski reported last week that Middleton would turn down his player option, he added that Middleton and the Bucks planned to work together on a new deal. Since then, Middleton’s name has barely popped up in the rumor mill, a hint that teams around the league view his return to Milwaukee as the most likely scenario.

So maybe the question shouldn’t be whether Middleton will be back, but whether his lucrative new contract (which could be worth up to as much as $189MM+ over five years) will be a worthwhile investment.

Despite earning his first All-Star nod in 2018/19, Middleton probably doesn’t qualify as a “star.” The 27-year-old is one of the league’s more reliable three-and-D options, but he has only cracked 20 PPG in a season once and was up and down in the playoffs this year. In the Bucks’ six-game series loss to the Raptors, Middleton struggled to slow Kawhi Leonard and averaged just 13.7 PPG.

Still, the Bucks have little choice but to commit big money to Middleton. Milwaukee isn’t a prime free agent destination, so it’s not as if the team can go out and recruit Klay Thompson to replace him. All of the Bucks’ moves this offseason will be made with an eye toward eventually securing a long-term commitment from Antetokounmpo, and allowing the team’s ostensible second-best player to walk in free agency wouldn’t be a good look.

Middleton’s new contract probably won’t be one of the NBA’s best values over the next several years, but the Bucks can’t afford not to offer it.

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Five Key Offseason Questions: Houston Rockets

After coming agonizingly close to the NBA Finals in 2018, the Rockets were once again the most serious threat in the Western Conference to knock off the Warriors in 2019. This time around though, the two teams met in the second round, and Houston blew a golden opportunity, losing Game 6 to a Warriors team that was missing Kevin Durant.

Unlike in 2018, when the Rockets could point to Chris Paul‘s hamstring injury and a fluky 0-for-27 run on three-pointers in Game 7 as reasons why they couldn’t sneak past the Warriors, this year’s loss felt more demoralizing, and the team doesn’t appear quite as likely to simply run things back with the same core.

Here are five key questions facing the franchise this summer:

1. How real is this Jimmy Butler thing?

Multiple reports in recent weeks have identified Jimmy Butler as the Rockets’ top free agent target. Houston is reportedly “extremely confident” about its chances to land Butler. There are just a few potential roadblocks:

  • Butler’s level of interest in the Rockets remains unclear.
  • Butler will command a maximum salary of $32.7MM and the Rockets have no cap room.
  • The Sixers would have to agree to sign-and-trade Butler to Houston, despite the fact that allowing him to walk could create significant cap room.
  • Base year compensation restrictions would likely force the two teams to involve a third club for salary-matching purposes.
  • Even if the Rockets could work out a deal, it would almost certainly cost them Eric Gordon, Clint Capela, and maybe other pieces.
  • The Rockets would become hard-capped at the tax apron by acquiring a player via sign-and-trade, substantially limiting their ability to add reinforcements around James Harden, Paul, Butler, and perhaps P.J. Tucker.

The sheer number of obstacles standing in the way of a Rockets acquisition of Butler should make it a long shot. And even if GM Daryl Morey could pull it off, I’m not convinced it would be the right move. Harden, Paul, and Butler all have big personalities and ball-dominant playing styles that could clash. The hard cap would limit Houston’s ability to acquire quality depth. And making further trades would be nearly impossible due to a lack of mid-level type salaries on the Rockets’ books.

It’d be a mistake to rule out the possibility of Butler – a Texas native – heading to the Rockets, given the creativity we’ve seen from Morey over the years. But if the Sixers are willing to offer Butler five years at the maximum salary or something close to it, I have to imagine it’s back to the drawing board for the Rockets’ front office.

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Five Key Offseason Questions: Boston Celtics

No NBA team besides the defending-champion Warriors had higher expectations entering the 2018/19 season than the Celtics. After all, they’d come within one game of reaching the NBA Finals during the spring of 2018 without having Kyrie Irving and Gordon Hayward in their lineup. With those two stars back and LeBron James leaving the conference, what could go wrong?

As it turns out, a whole lot. The Celtics were disappointing and dysfunctional all season long, with Irving’s and Hayward’s returns resulting in an overcrowded rotation that led to chemistry issues. In an Eastern Conference that only really had three legit contenders, Boston earned the No. 4 seed and won a first-round series, but the team didn’t come close to winning the conference and may be headed for a major overhaul this offseason.

Here are five key questions facing the franchise this summer:

1. Are Kyrie Irving and Al Horford really goners?

Last fall, Irving announced to Celtics fans at a preseason event that he intended to re-sign with the team when he became eligible for free agency in 2019. Players always talk in platitudes about wanting to stick with their current teams, but Irving’s declaration seemed different — it was more definitive, and it was unprompted, rather than a response to a reporter’s question.

Still, that apparent commitment to the Celtics came nine months before Irving would hit the open market, and as we noted at the time, he was always free to change his mind depending on how the Celtics’ season went. Sure enough, halfway through a year in which he repeatedly – and publicly – expressed frustrations with his team and teammates, Irving changed course, telling reporters in February to ask him “on July 1” about his intentions for free agency.

Now, a return to Boston looks like an extreme long shot. The Celtics and their fans appear to be moving on from the Irving era, with several reports indicating that the Nets are the frontrunners for the star point guard. It looks like Kyrie is a goner.

The same is true of Horford, which is even more unexpected. The veteran big man had fit in well with the Celtics since signing a four-year, maximum-salary deal with the team in the summer of 2016. He had a player option for 2019/20, but always seemed pretty likely to either pick up that option or to turn it down to negotiate a new contract with the C’s.

Instead, he’ll decline it to reach the open market, and the Celtics are now preparing to lose Horford as well, as rumors swirl about the possibility of a four-year, $100MM+ offer waiting for him in free agency. It’s hard to blame the C’s for being reluctant to match such an offer for a 33-year-old, and it’s hard to blame Horford for leaving Boston for a shot at one last monster payday.

It doesn’t appear there’s any animosity between Horford and the Celtics. It simply comes down to a difference in opinion on his value. That difference in opinion will leave Boston with a big hole in its frontcourt.

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Five Key Offseason Questions: Denver Nuggets

After missing the postseason by a single game in 2018, the Nuggets left no doubt about their spot in the playoffs in 2019, winning 54 games and claiming the No. 2 seed in the Western Conference.

Although Denver ultimately fell to Portland in the Western Semifinals, it was a hugely successful year for the organization, which won its first playoff series since 2009 as Nikola Jokic and Jamal Murray established themselves as one of the NBA’s most promising young duos.

Here are five key questions facing the franchise this summer:

1. What will the Nuggets do with Paul Millsap?

Eleven players from last season’s Nuggets roster remain under contract for 2019/20, include nine of the team’s top 10 players in terms of minutes per game. The only player in that top 10 whose situation remains murky is Millsap.

After being limited to 38 games in his first season in Denver due to a wrist injury, Millsap served as the team’s starting power forward in 2018/19, averaging 27.1 minutes per contest in 70 games. While Millsap’s numbers (12.6 PPG, 7.2 RPG) were relatively modest, he helped solidify the Nuggets’ defense and provided crucial veteran leadership on a young team.

I don’t have any doubt that the Nuggets would like to bring Millsap back. The only problem? The final year of his contract features a $30.35MM team option. That’s a steep price to pay for a 34-year-old who is no longer in the prime years of his career.

The Nuggets could probably afford to pick up Millsap’s option and maybe even still use the full mid-level exception in free agency, though they’d be right up against the tax line in that scenario.

Declining Millsap’s option and bringing him back at a lower salary would be an option, but once Denver turns down that option, he’ll be free to test the open market — there’s no guarantee he’d want to negotiate a more modest deal with the Nuggets after they’ve denied him what could be his final major payday.

While many big-money team and player option decisions are obvious, Millsap’s is one of the few that could legitimately go either way.

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Five Key Offseason Questions: Philadelphia 76ers

The Sixers took two major in-season gambles during the 2018/19 campaign, plucking Jimmy Butler from Minnesota and putting together a package of assets to acquire Tobias Harris from the Clippers.

The team’s five starters played in just 10 regular season games together due to various injuries and rest management. Those five saw their playoff run cut short in the second round after playing only 11 postseason games together as a group. The organization longs for an opportunity to get a larger sample size on its collection of talent.

Here are five key questions facing the franchise this summer:

1. How many starters will the Sixers bring back?

Philadelphia will face immense competition for Butler, Harris, and J.J. Redick on the free agent market.

Multiple teams are expected to offer Harris a max deal, with the Nets standing out as a noteworthy threat. The interest between Harris and Brooklyn is reportedly mutual. The Grizzlies, Jazz, Mavericks, Kings, and Pacers have all been linked to Harris as well.

Butler is confident he’ll also receive a full max and the Lakers will be among the teams looking to swoop in and steal the four-time All-Star. GM Elton Brand plans on doing everything he can to bring Butler back.

Redick’s underwhelming playoffs aside, his shooting will be coveted by many teams in the league. He made just over $12MM last year, though it’s unclear what the price range for him will be going forward as he prepares to enter his age-35 season.

The Sixers will be among the offseason winners if they can bring back all five starters and supplement them with an additional role player or two. Of the three pending free agents, I’d speculate Butler is the most likely to leave.

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Five Key Offseason Questions: Brooklyn Nets

After spending several years mired in NBA obscurity as the ramifications of an ill-fated trade with Boston limited their ability to acquire impact talent, the Nets finally broke through in 2018/19, earning their first playoff berth since 2015.

Suddenly, with the weight of the Celtics trade off their shoulders (Brooklyn’s 2018 first-round pick was the final piece of that deal), the Nets have a bright future ahead of them. They managed to add young talent like D’Angelo Russell, Caris LeVert, and Jarrett Allen in recent years despite a dearth of lottery picks, and they’re now positioned to bring in one or two star free agents to complement their young core.

Here are five key questions facing the franchise this summer:

1. What does the Nets’ Allen Crabbe trade signify?

It’s rare for two NBA teams to reach an agreement on a trade before the NBA Finals end, but the Nets and Hawks did just that last week, agreeing to a swap that will send Crabbe to Atlanta along with two first-round picks (this year’s No. 17 overall selection and next year’s top-14 protected pick). In return, Brooklyn will receive solid young wing Taurean Prince, Atlanta’s 2021 second-round pick, and – most importantly – additional cap flexibility.

The trade can’t officially be completed until July for cap reasons. But after removing the cap hold for the No. 17 pick ($2.96MM) and Crabbe’s expiring salary ($18.5MM) from their books and replacing it with Prince’s expiring deal ($3.48MM) and an empty roster charge ($897K), the Nets will have created about $17MM in extra cap space.

Before the deal, the Nets had no path to two maximum-salary slots and wouldn’t have had enough space for even a single max free agent if they’d retained Russell’s cap hold. Now, even if Russell sticks around, the club can comfortably afford a max-level player along with a second free agent above the mid-level. Renouncing Russell would clear a path to two max slots (with a caveat, as we’ll explain in the next section).

Teams generally don’t make this sort of move unless they know something — the Nets aren’t giving up two first-round picks to shed salary unless they’re pretty confident that the extra cap space will come in handy.

It’s probably not a coincidence that rumors linking Kyrie Irving to Brooklyn heated up right around the same time this deal was agreed upon. While things could change in the next few weeks, the possibility of Irving becoming a Net looks increasingly likely in the wake of the Crabbe trade, as a Thursday report suggested.

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Five Key Offseason Questions: Utah Jazz

After a torrid second-half run to finish the 2017/18 season, the Jazz entered the 2018/19 campaign widely viewed as a probable top-four seed in the Western Conference. A brutal first-half schedule ultimately prevented Utah from reaching that goal, but the team finished strong again and reached the 50-win mark.

Unfortunately, for a second straight postseason, the Jazz found themselves matched up against their nemeses in Houston, and were unable to take more than a single game from the Rockets. The Jazz had a pretty quiet offseason a year ago, but in the wake of their early exit from the playoffs, they appear far less likely to run it back with the same roster again.

Here are five key questions facing the franchise this summer:

1. How drastically will the Jazz change their roster?

A year ago, the Jazz bet on continuity and the continued improvement of young players like Donovan Mitchell and Dante Exum. The team figures to take a different approach this time around, as newly-promoted president of basketball operations Dennis Lindsey indicated at season’s end.

“We want to move the group forward,” Lindsey told reporters after the Jazz were eliminated from the postseason. “And while we have a very good team, the results told us that we don’t have a great team.”

Lindsey’s comments suggest changes are on the way, but we know that the Jazz aren’t about to rebuild their roster from the ground up. Mitchell and Rudy Gobert are safe. Joe Ingles probably isn’t going anywhere either. However, there may not be many guarantees beyond that.

Derrick Favors has been in Utah since coming over from the Nets as the centerpiece of the Deron Williams trade in 2011, but his $17.6MM salary for next season is non-guaranteed, and he isn’t a lock to return.

Ricky Rubio has been the Jazz’s starting point guard for the last two seasons, but he told an international outlet earlier this month that he may not be in the team’s plans going forward.

The Jazz have been high on Exum since selecting him fifth overall in the 2014 draft, but after another injury-plagued season, it’s not clear how much longer the Australian point guard will be a fixture in Utah.

The Jazz’s core isn’t going anywhere, but there’s a possibility the pieces around them will look significantly different in 2019/20.

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