With the bulk of the superstars originally expected to headline 2021 free agency now signed to extensions, the NBA's attention has shifted to the less-heralded class of 2022. With Stephen Curry expected to re-sign with the Warriors before then and Bradley Beal appearing like a trade candidate this offseason, Zach LaVine may well be the most coveted free agent on the market that offseason... if he gets there.

The Bulls would obviously love to give him an extension prior to his free agency, but according to Bleacher Reports' A. Sherrod Blakely, rival executives do not expect LaVine to extend. That would indeed make him an unrestricted free agent in 2022, but there are a few circumstances in which the Bulls could offer him such an enticing deal that he'd have little choice but to re-up in Chicago. LaVine's contract negotiations could go one of four ways: 

  • LaVine will be eligible for a traditional veteran extension this offseason. Such a deal can last five total seasons (including any years remaining on the deal, so four new ones in LaVine's case), can start him off at a 20 percent raise in the first year of the new contract (so, starting at LaVine's $19.5 million salary for next season, would therefore start at $23.4 million) and can include eight percent annual raises thereafter. In total, this would allow LaVine to sign a new deal that would guarantee him roughly $104.8 million in new money over four years. When you see the next set of numbers, you'll understand why he's very unlikely to accept this offer. 
  • LaVine could, in theory, do nothing. Then, in the summer of 2022, he would be eligible to sign a five-year contract with the Bulls starting at 30 percent of the salary cap that would include eight percent raises, or a four-year deal with another team starting at the same figure but with only five percent raises. The projected 2022-23 cap is $115.7 million. Therefore, LaVine would be eligible for a five-year, $201.3 million deal with the Bulls or a four-year, $149.3 million deal with another team. 
  • If the Bulls want to pay LaVine more than the $104.8 million they are allowed to offer LaVine this offseason, they could use the CBA's renegotiate-and-extend mechanism to do so. The problem with doing so is that it requires cap space. Next season's projected cap is $112.4 million, which would make LaVine's 30 percent max around $33.7 million. That's $14.2 million greater than the salary his contract currently calls for, meaning the Bulls would need to create at least $14.2 million in space to bump him up to that figure. Currently, the Bulls have nine players on the books next season making around $99.3 million, so they are within striking distance of that figure. However, that would mean renouncing the cap holds of all of their own free agents, including Lauri Markkanen, and remember, if they want to add more talent through free agency, they'd have to create more cap space. They could clear an extra $15 million in space right off the bat by declining Ryan Arcidiacono's team option and waiving Thaddeus Young and Tomas Satoransky, who are both only partially guaranteed for next season, but those are all players the Bulls would like to keep. In other words, if the Bulls want to go down this path with LaVine, it would be extremely difficult for them to clear enough space to also chase a high-profile free agent. They have been linked to point guards like Lonzo Ball, so they would have to find an alternative method of acquiring such a player without the means to create enough space to sign that player outright. 
  • There is one hail mary scenario that would allow the Bulls to pay LaVine more than the $104.8 million they are currently allowed to without impacting their cap space. If LaVine makes an All-NBA Team this offseason, the veteran extension limitations would drop and LaVine would become eligible for a supermax contract. This would keep his 2021-22 salary where it is now, but give him an absolutely enormous deal afterward. The supermax starts at 35 percent of the cap in the year in which it kicks in and increases by eight percent annually. Based on current projections, that would pay LaVine roughly $234.8 million in new money, on top of the $19.5 million he is already owed for next season. If he doesn't sign an extension of any sort this offseason and then makes an All-NBA Team next season, he would be eligible for this contract with the Bulls next offseason. 

So what does all of this mean for LaVine and the Bulls in practical terms? If Chicago offers him that first extension, there's no reason to believe he'd take it. The best outcome for Chicago's short-term fortunes would be for LaVine to be named to an All-NBA Team so they could give him a market-value extension while preserving the cap space to improve the team around him. However, it should be noted that Chicago once traded Jimmy Butler specifically to avoid paying him the supermax. That is not a contract the Bulls have historically given out lightly. There's also no guarantee that LaVine takes it. At this point, we don't know enough about his priorities. If his sole goal is contending for a championship or playing in a certain type of market, he might prefer to sign elsewhere. But with Stephen Curry, Damian Lillard, Luka Doncic, James Harden, Kyrie Irving and Bradley Beal likely occupying the guard spots on the All-NBA Teams this season, for now, this scenario is unlikely to play out. 

The situation we are likeliest to encounter is Chicago offering LaVine that renegotiation and extension for just over $200 million. The Bulls would likely hope for an answer from LaVine before the beginning of free agency. That way, if he declined, they could pivot into using their cap space to add talent around him in the hopes that he'd re-sign in 2022. 

Ultimately, whether it's this offseason or next, Chicago will have an opportunity to present LaVine with an absolutely enormous contract offer. If money is his main priority, he will take it. Not only can the Bulls offer him a higher salary than any other team, but Chicago is the NBA's third-biggest media market. Being the face of the Bulls comes with plenty of marketing opportunities. 

But if LaVine's goal is winning, the Bulls still have a lot of work to do. They traded for Nikola Vucevic at the deadline hoping it would give LaVine another star to win with, but the duo is just 3-7 in their first 10 games together. That pairing is a nice start, but it's a long way from championship contention, and if the Bulls can't find a way to make further upgrades before LaVine makes a decision on his future, there's a good chance they're going to lose him to a stronger team.