Zach LaVine Chicago Bulls
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The Chicago Bulls are in a somewhat precarious situation when it comes to Zach LaVine's next contract. The first-time All-Star is only one year away from free agency, and if the Bulls want to keep him, they are going to have to pay up. Essentially, there are three feasible ways for him to re-sign in Chicago, and each is a minefield. 

  • The Bulls could offer LaVine a typical veteran extension this offseason. Such a deal would start at a 20 percent raise on his $19.5 million 2021-22 salary and pay him roughly $105 million in new money over four years. The problem here is that such a deal would be well below LaVine's max, and he is unlikely to accept such a deal. "I definitely want what I deserve," LaVine said at his end-of-season press conference in May. He deserves a good deal more than $105 million. 
  • If the Bulls want to pay LaVine his max immediately, they would have to renegotiate and extend his contract. This would involve giving him a raise to his max next season and agreeing to an extension based on that figure. The problem with doing so is that it would require cap space. LaVine would need a $14.2 million raise to get to his $33.7 million max next season. The Bulls can create that cap space, but doing so would be costly. The Bulls would have to renounce their rights to their other free agents, including former No. 7 overall pick Lauri Markkanen, and depending on what other moves they make, perhaps waive Thaddeus Young and/or Tomas Satoransky, who have partially guaranteed deals. This sort of extension could pay LaVine up to $195 million. The downside to doing this is that the cap space spent on LaVine couldn't be spent retaining or adding other players. 
  • If Chicago's goal is to put the best possible team around LaVine, their best move would be to make him wait. That way, they could use their cap space to sign supporting talent, including, perhaps, a starting point guard. They could then sign LaVine to a new deal in free agency next offseason. That deal would be only slightly pricier than the $195 million LaVine could get now at $201 million over five years. However, if they don't sign LaVine now, they risk losing him for nothing when he does become a free agent. 

That is the conundrum that the Bulls find themselves in. They can pay LaVine right now, but doing so would prevent them from building a winning a team around him. They can try to put that winning team around him, but if they fail, they might not be able to keep him at all. There is no easy solution here, and one misstep would risk alienating most players in this situation.

Fortunately for the Bulls, LaVine appears to be somewhat flexible when it comes to his next deal. He wants to make what he deserves, but he specified on the Bulls Talk Podcast that he understands the position that the Bulls are in. He says that he wants to remain with the Bulls whether a new deal comes this offseason or next. 

"With me, I try to let my agent handle everything," LaVine said. "But as long as it gets done, I'll be happy. I mean, obviously, I want to be with the Bulls and you don't want to implicate, you know, free agency, and I understand, like the cap room that goes into it with a sizable extension with me. So, I want the team to be good, but then I also want to be taken care of as well. I feel like I've done really well by the Bulls, and obviously I want to be here long term, and I feel like I deserve what I get. So, it is what it is. We'll figure [it] out when that comes. If it's this year, next year, we'll just see what happens."

If LaVine is, in fact, comfortable waiting, the Bulls should be able to pursue a big-name point guard in free agency this offseason. Right now, the Bulls are looking at around $10 million in cap space, but they can save quite a bit thanks to the partially guaranteed deals they've given various players in recent years. Only $6 million of the $14.1 million owed to Young is guaranteed, and only $5 million out of the $10 million owed to Satoransky is guaranteed. Ryan Arcidiacono's $3 million salary is fully non-guaranteed, and the Bulls can save around $7 million more by waiving and stretching Al-Farouq Aminu, who is owed approximately $10.2 million. Some combination of those cap clearing measures, in addition to renouncing their own free agents, could put the Bulls in position to chase a player like Lonzo Ball, Spencer Dinwiddie or Dennis Schroder to pair with LaVine in Chicago's backcourt.

Chicago would be taking a risk by going this route. They likely have the opportunity to lock LaVine up right now, and passing on it, even in the interest of improving the team around him, risks losing him a year from now. LaVine has never reached the postseason, and championship contenders will pursue him in 2022 free agency if he gets there. But if he has indicated privately what he is suggesting publicly, the Bulls may have enough faith that the will re-sign to use this offseason as an opportunity to support LaVine rather than pay him.