Sometime between now and the 2020 NBA draft on Nov. 18, the league should lift the monthslong transaction moratorium, allowing its annual round of offseason chaos to officially begin.
There are many things the NBA will need to sort out quickly, from the salary cap rules governing next season to where games will be played. Those negotiations and conversations with public health officials are an immediate priority for commissioner Adam Silver and National Basketball Players Association executive director Michele Roberts. The league is currently pursuing a pre-Christmas Day start and a reduced regular-season schedule for the 2020-2021 season, sources told ESPN's Adrian Wojnarowski and Brian Windhorst.
But teams are also getting ready to navigate the unpredictable roster shuffle that hits the league every offseason. It's been more than eight months since the most recent NBA trade and more than 15 months since the last big move of the 2019 NBA offseason, when Russell Westbrook was dealt for Chris Paul. That silence will end quickly.
To preview what's to come, and where the real transaction power is held, here's our list of the people who will be making the biggest decisions this offseason, all their options and the potential fallout.
Giannis Antetokounmpo: The superstar everyone wants
Option 1: Sign a supermax extension
There is no more impactful decision this fall than whether the reigning two-time MVP will choose to sign the five-year extension he will be offered at the start of free agency by the Milwaukee Bucks. That would cement the Bucks as title contenders well into the 2020s.
But it would also alter the plans of the teams hoping to lure Giannis Antetokounmpo away. The Toronto Raptors won't be as scared by an offer to unrestricted free-agent point guard Fred VanVleet that could damage their cap sheet. And the Miami Heat and Dallas Mavericks could look to bolster their rosters now with long-term money that previously would have been unpalatable.
Don't expect an immediate spending spree if Antetokounmpo re-signs -- the 2021 class will still have star power, and the league is carefully navigating pandemic finances -- but his potential availability will keep some teams in wait-and-see mode until he signs his next contract.
Option 2: Hold off on a decision until 2021 free agency
Multiple sources have emphatically said Milwaukee will not look to trade Antetokounmpo if he passes on the extension. Instead, the Bucks will try to improve their roster and use the next year to show Antetokounmpo why he should stay.
Waiting would give Antetokounmpo maximum leverage over Milwaukee over the next 12 months. If the Bucks are willing to add to their payroll to improve the team -- something ESPN's Adrian Wojnarowski has reported they are -- Milwaukee could chase a significant upgrade in trades (despite being short on prime assets).
Victor Oladipo and the Pacers' front office: The expiring deal
Option 1: Pursue an extension
With one year left on his contract, Victor Oladipo looks like a possible extension candidate. But finding a number that makes sense for both sides won't be easy.
The Indiana Pacers can offer an extension beginning at 120% of Oladipo's salary for the 2020-21 season -- a deal that would start around $26 million, a few million per year below what he could sign on a max contract next offseason as an unrestricted free agent. Oladipo, who suffered a torn quadriceps tendon in January 2019 and then struggled upon returning this year, could want to come back next season and try to prove he's still the All-NBA player he was in 2018.
Option 2: Gauge trade options
There is a reason Oladipo's name has been mentioned for months as a possible trade target. Having just one year left on his deal puts the Pacers in position to potentially lose him for nothing -- something a small-market team would always prefer to avoid. And the financial landscape of both the league as a whole and the Pacers specifically (with long-term money already committed to Malcolm Brogdon, Myles Turner and Domantas Sabonis) has rival teams wondering if they will be willing to spend to keep Oladipo.
But any trade talks here will be complicated. Oladipo's play was uneven after returning from injury this year, and given his history, those concerns would transfer to a new team.
Option 3: Wait it out
Even if this leads to Oladipo walking in a year, it could be the path that makes the most sense for both sides. The Pacers likely won't trade Oladipo for a low-value package just to move him. Waiting would give Indiana a chance to see what this core looks like at full strength before reevaluating things at the 2021 trade deadline, and would give Oladipo a chance to show he's back to who he was pre-injury.
Fred VanVleet: The best available free agent
Option 1: Re-sign in Toronto
The Raptors have two primary goals this offseason: re-sign guard Fred VanVleet, and do so without eating too much into their max cap space for 2021.
According to ESPN's Bobby Marks, any VanVleet deal around four years and $80 million should keep Toronto in the superstar race next offseason. But things get dicey if the Raptors start competing with bigger offers for one of their most important players.
Option 2: Join a rebuilding team
Two years ago, VanVleet bet on himself in free agency, signing a two-year, $18 million deal that he far surpassed in terms of on-court value. Now he enters free agency as possibly the best unrestricted player with a chance to relocate. The teams swimming in cap space -- such as the Detroit Pistons, New York Knicks and Atlanta Hawks -- missed the playoffs, so VanVleet could be choosing between taking a little less to play in a winning situation or a little more to try to turn around one of those teams.
In both Detroit and New York, he could be a culture setter in the middle of a rebuild. Atlanta has designs on taking a big step forward next season, and having a secondary creator, shooter and defender next to Trae Young makes a lot of sense.
Travis Schlenk: The GM with money to spend
Option 1: Commit to long-term additions
Rival teams expect Atlanta to look to make substantial improvements this offseason. If the Hawks can add depth around their young core of Trae Young, John Collins, Kevin Huerter, De'Andre Hunter, Cam Reddish and Clint Capela, they can enter the suddenly competitive playoff mix in the Eastern Conference.
With $42 million to spend, general manager Travis Schlenk can make competitive long-term offers that most teams won't be able to top. The Hawks won't find a proven star in this class, but there are good players -- including VanVleet, Davis Bertans, Danilo Gallinari and Joe Harris -- who could add much-needed shooting and defense.
Option 2: Look at short-term improvements
The alternate route here is bypassing an extension for Collins (waiting to re-sign him until he's a restricted free agent after this season) and getting the best possible players now on one-year deals. That would allow the Hawks to walk into next year's free agency with a full max salary slot and attempt to recruit a star after what they hope is an impressive season.
Clippers and 76ers: The high-pressure disappointments
Option 1: Count on a new coach and new results
The LA Clippers were the favorites to win the NBA title for most of the season before sputtering out of the playoffs in the second round. The Philadelphia 76ers hardly ever saw their projected starting lineup on the court together.
That could cause both teams to say that the only change they needed to make was on the bench -- where Tyronn Lue replaced Doc Rivers in Los Angeles and Rivers replaced Brett Brown in Philadelphia.
Option 2: Big moves
Both teams are under intense pressure to win, making them candidates to pursue roster changes before the season tips, though dramatic overhauls will be complicated.
In Los Angeles, Paul George and Kawhi Leonard almost certainly aren't going anywhere. And after the trade for George last summer, the Clippers don't have many assets to send out. They could try to combine players such as Patrick Beverley, Lou Williams and Ivica Zubac in deals, but it's tough to trade veteran role players for impact talent. They could also try to execute sign-and-trade deals for Marcus Morris and/or Montrezl Harrell, but the math there is tricky.
In the East, can the Sixers find a taker for Al Horford and balance their roster? Will they consider moving on from Josh Richardson, who has one year left on his deal? Will Ben Simmons play point guard, like he has most of his career, or power forward, like he did in the Florida bubble before suffering a season-ending knee injury? And if Simmons is at the 4, where does Philly find a point guard? The answers to any of those questions could lead to roster changes in Philly.
Bob Myers and Sean Marks: The allure of more star power
Option 1: Win-now moves
As my colleague Brian Windhorst is fond of saying, "Winning a championship means never having to say you're sorry." We've seen teams go all-in on star power in each of the past two summers and win it all. The Golden State Warriors and Brooklyn Nets could find themselves with similar opportunities this offseason.
For Bob Myers, Golden State's president of basketball operations, that would mean trying to use the No. 2 pick in this year's draft and the lightly protected future first-rounder from the Minnesota Timberwolves (along with the bloated contract of Andrew Wiggins) to add another high-level player to a core of Stephen Curry, Klay Thompson and Draymond Green. For Sean Marks, Brooklyn's general manager, that means potentially dangling a package including the Nets' enticing young talent -- Caris LeVert, Spencer Dinwiddie and Jarrett Allen -- to add a third star alongside Kevin Durant and Kyrie Irving.
Option 2: Build for the long haul
In the NBA, there is always the possibility some star player shakes free whom no one is expecting, but right now there isn't an obvious trade target for either team.
That is especially true for Golden State, which is unlikely to trade an asset like the No. 2 pick in the draft for a moderate upgrade. If there isn't an obvious deal now, the best bet for the Warriors might be to simply make their pick, bide their time and see what opportunities pop up.
Brooklyn, on the other hand, already has plenty of nice complementary pieces for Durant and Irving -- a formula we just saw work for the champion Lakers. With Durant and Irving both signed for multiple years, the Nets have time to see what they have before trading their young players.
Sam Presti and David Griffin: The playoff bubble teams
Option 1: Embrace a rebuild
Last summer, both Sam Presti (the Oklahoma City Thunder general manager) and David Griffin (the executive vice president of the New Orleans Pelicans) had franchise players requesting trades to relocate to Los Angeles. Both turned those situations into huge hauls of young talent and draft assets.
They could attempt to do the same this year, though the returns shouldn't be as big. After trading for Chris Paul and Danilo Gallinari, Presti could try to extract further value by flipping them this offseason. Paul's bloated contract (he's owed roughly $85 million over the next two seasons, including a $44 million player option in 2021-22) could make moving him difficult but also should lower OKC's asking price. Gallinari is an unrestricted free agent, but because of the lack of available cap space on good teams, he could be a candidate for a sign-and-trade deal.
Griffin has a decision to make about Jrue Holiday. One of the league's best defensive guards, Holiday has one year left on his deal, and in an offseason when there isn't a lot of star power available, he could fetch a nice return for the Pelicans, allowing them to fully commit to building around Zion Williamson and Brandon Ingram.
Option 2: Maintain playoff contention
If Paul and Holiday stay put, both teams will hope to again remain in the playoff chase. Oklahoma City might have difficulty doing that if the team doesn't retain Gallinari, but given the lack of clear suitors for him this offseason, the Thunder might be able to re-sign him and try to flip him down the road.
Meanwhile, New Orleans was the favorite to be the eighth seed before things went sideways in the bubble -- and the Pelicans will be confident they can make a run at a playoff spot next season if Williamson is healthy and Holiday is still on the roster.
Anthony Davis: The contract question
Option 1: Commit long term
After teaming up with LeBron James to win a championship in his first season in Los Angeles, it's hard to envision Davis going anywhere when he becomes an unrestricted free agent this fall. Assuming he does re-sign with the Lakers, Davis will have a choice to make: sign a short-term deal -- one or two seasons -- or a full four- or five-year max contract.
If Davis chooses the long-term route, the Lakers can more easily plan around his salary commitments as they look to bring in more stars in the future and to supplement the roster next season.
Option 2: Go the short-term route
A shorter-team deal shifts the power dynamic in Davis' direction. If he signs a two-year deal, that would allow him to sign a max contract for the most money -- 35% of the salary cap -- in 2022. A one-year deal would allow him to align with James, who can also become a free agent after next season.