That is when reigning MVP Giannis Antetokounmpo is set to become an unrestricted free agent. Teams have focused on being set up to chase Antetokounmpo and other stars two summers from now, putting the league's typically nonstop transaction game on hold.
And while the NBA is currently in a moment of stability, there are important moments that could shake up the league before the summer of 2021. There's potential for blockbuster trades that will impact future title races,much like 2019's free agency brought. As the NBA returns from its midseason break, here is a look at what could be the most dramatic inflection points over the next 17 months.
The 2020 postseason
1. What if the Houston Rockets flame out of the playoffs?
What's at stake: The Rockets have been one of the NBA's best teams since acquiring James Harden in 2012 (third-best regular-season record, fourth-most postseason victories), but this spring could mark the end of an era. By trading for Russell Westbrook and Robert Covington, Houston has gone all-in on the season by fully embracing small ball.
After an on-again, off-again contract extension negotiations, coach Mike D'Antoni is in the final year of his deal. Even though Harden is under contract through 2021-22, does he look for other options if things go south?
What league insiders expect: If the Rockets fail to advance deep into the postseason, the consensus is that D'Antoni returning would be unlikely. People around the league are less certain about general manager Daryl Morey's future, though.
Meanwhile, voluntarily moving Harden isn't expected to be in play. But whether Houston can remain a part of the contending group going forward remains up for debate.
"It's a league of elite-level players," one executive said. "If you have one or more of them, you can generally figure the rest out."
"I think they're a house of cards, man," another said. "They don't have any depth. There's nothing credible there."
2. What if the Philadelphia 76ers can't make it work?
What's at stake: The Sixers have been mired in turmoil despite some success and return from the All-Star break in fifth place -- as a dreadful road record (9-19) has prevented them from capitalizing on league-best play at home.
If Philadelphia fails to advance past the second round for the third straight season, the job statuses of coach Brett Brown and general manager Elton Brand will come into question -- and the possibility of trading either Ben Simmons or Joel Embiid will gain traction.
What league insiders expect: Most don't expect Brown to be retained if Philly loses early in the playoffs. But would they actually break up the Simmons-Embiid duo?
There is no consensus, but league execs think that if the Sixers do explore a trade, Embiid is more likely to be moved -- health being the determining factor in building around Simmons. One exec added that a big trade featuring Simmons or Embiid might be the only way to reshape the team.
"If they tried to move [Tobias Harris or Al Horford], I don't think they'd get value in return," a league executive said. "They'd ask to be incentivized. Whereas if they move Ben or Joel, they'll get a lot more."
3. What if the Golden State Warriors win the lottery?
What's at stake: The Warriors have two options this summer: Use their lottery pick to add a young building block to the organization or combine it with the pick they received in the D'Angelo Russell-Andrew Wiggins trade to add another star.
If a player such as Bradley Beal demands a trade, would the No. 1 pick (in a questionable draft) give the Warriors an appealing enough package?
What league insiders expect: Most league executives expect the Warriors to package their assets in search of a fourth star. However, some believe Golden State wouldn't mind rolling with Wiggins and a couple of high-ceiling prospects to extend a dynastic run as the championship core ages.
"Their coaches think they can cure Wiggins," an executive said. "If he's your fourth-best player, it's not a bad thing. But he needs to hide, because he can't do it every night."
There also are tax concerns ahead. If the Warriors use their first-round pick, the midlevel exception and the full trade exception, they will be the most expensive team in NBA history. While the expectation is that Golden State will spend heavily this summer, there are some who question whether it will utilize every ounce of its spending power -- even with the increased revenue generated by the new arena.
The 2020 offseason
4. What will Giannis do on June 30?
What's at stake: Players this good rarely become available in their prime.
If Giannis stays and signs a five-year supermax extension with the Milwaukee Bucks, they become a firm title contender for years. And taking him out of the 2021 free-agent class could inspire movement from teams that were holding onto space. But if Antetokounmpo doesn't commit right away, every franchise with a chance will be putting together trade offers.
What league insiders expect: Given how well the Bucks are playing, every executive we spoke to expects Antetokounmpo to re-sign with Milwaukee. The Bucks are overwhelming favorites to reach the NBA Finals, and falling short of that bar looks to be the only thing that could put Milwaukee's MVP in play.
5. How will the lack of cap space impact this summer?
What's at stake: Only a few teams are currently projected to have significant cap space in July. And each of them -- the Atlanta Hawks, Cleveland Cavaliers, Detroit Pistons, Charlotte Hornets and New York Knicks -- is either in an undesirable free-agent destination, a terrible team or both.
Combine that with a lackluster free-agent class and this summer should be dominated by sign-and-trade talk, key midlevel additions, player option decisions and possibly drawn-out restricted free agent negotiations.
What league insiders expect: Most expect Andre Drummond and DeMar DeRozan to opt into the final year of their respective deals, allowing them to enter a more lucrative market in 2021.
What happens with New Orleans Pelicans All-Star Brandon Ingram in restricted free agency is more divisive. Most executives believe Ingram isn't worth a max contract, which makes his future difficult to predict.
"I wonder if [Pelicans executive vice president of basketball operations David Griffin] will hardball [Ingram] and say, 'Get an offer,'" one executive asked. "Where is he getting it from?"
Another exec went the other way, suggesting Griffin could offer Ingram a full max to ensure he couldn't take a short-term deal elsewhere, cementing him as the No. 2 option alongside Zion Williamson.
"Securing the extra year and not allowing him to sign a two-plus-one with someone is worth it," the executive said. "Is the few million less you might save really worth the extra year?"
6. Do any star players become available in trade talks?
What's at stake: Had Beal not agreed to a contract extension in October, he would have been the top name in this year's trade market. Once we hit the offseason, he'll be eligible to be moved again. A top-15 player stuck on a rebuilding team, Beal has the potential to entirely reshape the 2021 title race if he lands on a contender.
One other name to watch: Indiana Pacers guard Victor Oladipo, who only recently came back from a ruptured quad tendon. Next season will be the final year of his contract, which generates questions about any star player's future.
What league insiders expect: Rather than exploring trades as early as the draft, Beal and theWashington Wizardswill likely wait to evaluate John Wall's recovery after he returns from his Achilles tendon injury. Persistent poor play by Washington next season could put Beal in play, but NBA execs aren't expecting the Wizards star to be available come July.
It's too early to really project what will happen in Indiana before the Pacers make a playoff run -- and many still expect Oladipo to stay long term -- but this could be something to monitor between July and the 2021 trade deadline.
7. How will LeBron age?
What's at stake: It's easy to forget the fact thatLeBron Jamesturned 35 in December. AssumingAnthony Davisreturns, the only real ways theLos Angeles Lakerscan improve heading into next season are with roster exceptions or finding a valuable trade package for Kyle Kuzma.
If James endures some natural decline, Davis probably needs to be ready to take on an even larger role and the Lakers need to find both a capable shot-creator plus another reliable 3-and-D wing to make life easier on James.
What league insiders expect: The consensus is that James will continue to gently decline but still remain one of the best 10 or so players in the league.
"I have no reason to believe he's going to drop off," one executive said. "He still looks like he can do s--- that he could 10 years ago."
But there was agreement that the Lakers really need to nail their 2020 offseason moves -- either in free agency, trades or both. This roster is working, but the rest of the Western Conference is improving and most of the other contenders have clearer paths to add talent.
"Kuzma is the one piece they have to really use to get better," another executive said. "How are they going to build another sustainable team?"
8. How will Kevin Durant reshape the East?
What's at stake: After Durant tore his Achilles last June, his return to the floor has a chance to completely change the Eastern Conference.
For theBrooklyn Netsto surpass the East's other elite teams, they'll need the best version of Durant. And whether he is 100 percent or not, they'll enter the 2021 trade deadline with enormous questions about how to handle their deep collection of talent.
What league insiders expect: People around the league are hopeful Durant can come back at something approaching the player he was before. But the combination of his age (32 next season) and the severity of the injury makes insiders uncertain he'll be the same superstar at the start of the season.
"I think Durant will probably have the worst year of his career," an executive said. "No fault to him, but people don't come back from Achilles injuries and tear the league up.
"It's all relative. In the worst year of his career, he might be the 25th-best player in the league, and they might win 50 games. I just don't see them being a realistic contender barring some moves."
Several people mentioned the Nets could be active in trades. Spencer Dinwiddie, Caris LeVert and Jarrett Allen are all names that rival executives believe to be available in some form. They could be attractive pieces for the Nets to package together to land a third star that sends them to the top of the conference. Some also wonder whether Brooklyn will spend big to keep unrestricted free agent Joe Harris this summer.
9. Will 2021 free agency be worth the hype?
What's at stake: Teams are hoarding 2021 cap space for a free-agent summer that could include Antetokounmpo, James, Oladipo, Kawhi Leonard, Paul George, Rudy Gobert, Gordon Hayward, Mike Conley, Kyle Lowry, Jrue Holiday and LaMarcus Aldridge.
But while the summer of 2021 looks more promising than that of 2020, it would be difficult to replicate 2019's league-shifting circus.
What league insiders expect: Antetokounmpo's decision will be pivotal, but even if he does remain on the market, the players behind him are not nearly as attractive to rival executives as their names might suggest.
"It's got a lot of name-value guys," one executive said. "But I do think it's being overhyped because a lot of the guys are considerably older."
Hayward, Conley, Holiday, Aldridge and Lowry are all on the wrong side of 30. They could improve a contender, but they won't really swing things themselves. And James, Leonard, George and Gobert (for now) all appear unlikely to leave their current teams.
Some of this is simply an outgrowth of the way the league operates now. With shorter contracts and more players electing to hit free agency, the churn hardly stops.
"I used to keep four-year and five-year depth charts for every team," another executive said. "You can't do that now."
Windhorst: Supermax deals are failure if Giannis leaves Bucks
Brian Windhorst explains why the ideology behind supermax deals in the NBA is in jeopardy if Giannis Antetokounmpo does not sign a contract extension with the Bucks.