Bill Simmons proposes 3 trades to spark a rebuild for the Chicago Bulls

It wasn’t too long ago that The Ringer creator Bill Simmons was speculating Anthony Davis could possibly be available on the trade market as a win-now move for a team like the Chicago Bulls, but it seems it hasn’t taken him long to do a complete 180-degree turn from his previous take. Now, Simmons feels confident that a rebuild is the best plan of action for these Bulls after a 9-12 start to the season.

In his most recent podcast, Simmons went over a trio of potential trades that would not only bolster Chicago’s long-term outlook, but grant the team what feels like a true direction for the first time since 2016.  Unfortunately, a few core members of this roster would become casualties in the process, should the Bulls eventually decide to follow his advice.

Listen in on this two-minute clip regarding what Simmons had to say about the Chicago Bulls in 2022-23.

The Ringer’s Bill Simmons believes the Chicago Bulls could commit to a convincing rebuild by making these 3 trades.

Simmons kicks things off by immediately proposing a blockbuster trade that would radically alter the course of Chicago’s future. In this trade, the Bulls exchange DeMar DeRozan and Nikola Vucevic for a pair of draft picks in the distant future and Russell Westbrook, who essentially amounts to little more than salary filler for a tanking squad.

It is interesting, however, that this offer is just a better version of the commonly rumored package the Lakers wanted from the Pacers in Myles Turner and Buddy Hield. If Indiana rightfully believes they can get more on the trade market that LA can offer, then why on Earth would the Bulls give up even more? That being said, if the Bulls were intent on trading DeRozan, I wouldn’t mind seeing the team do right by DeMar by trading him to his hometown team — just not for this package.

Simmons then pivots from this by proposing a trade that would send Zach LaVine to New York, effectively tearing down the incumbent Big 3 in an effort to bottom out.

Somehow, this return is even worse than the first, and seems to be completely predicated on the uncertainty surrounding Zach LaVine‘s knee recovery. Simmons believes the Bulls should panic regarding Zach and trade him for a paltry package of assets. He explicitly mentions Obi Toppin and the 2023 pick, as well as “salary filler” to compensate for LaVine’s massive contract. Evan Fournier and Derrick Rose would almost certainly fill this spot in any hypothetical trade scenario. As much as I’d like to see Rose back in Chicago, mortgaging their best player for a temporary heartwarming reunion would be a terrible decision on the Bulls’ behalf,

After tearing down the Bulls’ current core, Simmons finally returns to the realm of plausibility with a proposed trade for Alex Caruso. Considering Caruso has established himself as one of the best defensive bench pieces in the NBA on an extremely team-friendly deal, Simmons seems acutely aware that several teams would be interested in acquiring his services.

If Chicago did in fact deal away their Big 3, trading away Alex Caruso for a player that better fits the Bulls’ timeline makes a lot of sense on paper. Whether or not this exchange makes as much sense for the Warriors, however, is a subject worth approaching apprehensively. As much as Caruso would help replace the loss of Gary Payton Jr. from last year’s championship squad, I don’t see Golden State committing this many assets to acquire a role player.

This is how Chicago’s depth chart would look if these deals actually took place.

• PG: Ayo Dosunmu, Derrick Rose, Goran Dragic, Russell Westbrook
• SG: Coby White, Moses Moody, Evan Fournier, Donte DiVincenzo
• SF: Patrick Williams, Javonte Green, Dalen Terry
• PF: Obi Toppin, Derrick Jones Jr.
• C: Andre Drummond, Tony Bradley, Marko Simonovic

Simmons seems to feel confident this temporary step back would ultimately result in a net gain long-term, but I’m not so sure. As much as I’d like to see the team stock up on future draft capital and slot Pat in his natural fit at small forward, I don’t think this is the best play for the Chicago Bulls right now. This much is especially true considering Chicago does not even own its draft pick this year, making the decision to buy into the Victor Wembanyama sweepstakes far too risky of a gambit to stomach.