Alonzo Adams (USA Today)

Danilo Gallinari is entering free agency at the peak of his value. While injuries have limited his leverage in previous negotiations, he missed only 10 games with minor issues during the 2019-20 season and averaged 18.7 points on 40.5 percent shooting from behind the arc. Both are the third-best averages of his career. Gallinari is one of the best forwards in basketball, but at 32 years old, he won't have many more opportunities to cash in. 

But he's also running out of chances to win a championship. Gallinari has never won a playoff series, but as he ventures back into free agency, it is up to him to decide whether he should prioritize winning or money. In an interview at Italy's Festival dello Sport, Gallinari revealed his plan, according to international sports publication Sportando. When the interviewer asked, "is playing for the NBA Championship more important than a contract?" Gallinari responded "Yes. At this time, yes. I'm not 20 anymore."

For now, that likely means that Gallinari will not return to the Oklahoma City Thunder. While they made a surprising run into the playoffs last season, they are expected to trade Chris Paul and move into a rebuild this offseason. 

Gallinari could potentially find another contender to play for, but it would mean making an enormous financial sacrifice. The only contending team that has a feasible path to generating max cap space is the Miami Heat. The Heat very nearly traded for Gallinari at the deadline, but the deal fell through. It isn't clear whether that was the result of failed contract negotiations with Gallinari or an inability to agree on compensation with the Oklahoma City Thunder, but bringing in Gallinari now seems unlikely for the Heat. Their cap space disappears if they choose to re-sign their own free agents, and in all likelihood, they prefer the idea of keeping Goran Dragic and Jae Crowder to pursuing Gallinari. Even if they are interested, their offer probably wouldn't exceed one season. The Heat are expected to pursue Giannis Antetokounmpo in 2021 and need a clear cap sheet to do so. 

Realistically speaking, Gallinari would need to either take the Mid-Level Exception or engineer a sign-and-trade to get to a contender. Unless he's willing to take a truly steep discount, that knocks out teams like the Warriors, Nets, Bucks, Rockets, Celtics and 76ers. Those teams are so close to the tax line that the full Mid-Level Exception is not feasibly available, and acquiring a player through a sign-and-trade hard-caps those teams, so unless the Thunder are willing to take back some extra money to facilitate a deal, a trade seems unlikely. 

There are a few contenders potentially positioned to use either the full Mid-Level Exception or engineer a sign-and-trade. In no particular order, here are the notable ones:

  • Depending on how many of their own players the Lakers retain, they could potentially use the full Mid-Level Exception. They also have enough expiring money (primarily through Danny Green) to engineer a workable trade. 
  • The Nuggets are roughly $30 million below the projected tax line. They are expected to use that money to retain their own players, but if they decide to be a bit more aggressive, bringing Gallinari back to Denver might be an option. 
  • The Mavericks can use the full Mid-Level Exception, but like the Heat, they are expected to preserve their cap space for 2021. Still, a one-year offer at around $9.3 million might tempt him. 
  • The Clippers and Raptors will probably look to retain their own players first. If the Clippers lose Montrezl Harrell or Marcus Morris, though, they could pivot into the full Mid-Level Exception. The Raptors will focus on getting Fred VanVleet locked up and hopefully securing Serge Ibaka and/or Marc Gasol on one-year deals (to preserve their own 2021 ambitions), but like the Clippers, could change gears depending on what happens to their own players. 

Ultimately, we don't know just how far Gallinari is willing to go in pursuit of a ring. If he trusts himself to remain healthy and productive, he could theoretically take the Taxpayer Mid-Level Exception (roughly $5.7 million last season) from one of the teams listed above and use a contending season to secure a bigger contract in the far more fruitful 2021 cap environment. If he decides to make more immediately, his list of suitors shrinks. 

Gallinari fits onto almost any contender. His shooting is universal. But 32-year-olds only have so many opportunities to make life-changing money. What he ultimately decides to do will likely depend on what sort of offers he gets from contenders and from the weaker cap space teams. There might be an amount so great he can't turn it down. But if the depressed market limits his financial upside, there is a reasonable argument in favor of taking a one-year pact, trying to win a title, and then making his money a year from now.