The Chicago Bulls appear to be finally facing the music; after yet another dispiriting loss on Monday night against the Milwaukee Bucks, the team is now reportedly looking to officially put former All-Star wing Zach LaVine on the trade market. LaVine, even though he'll be making $177 million for the next four years, should net Chicago a pretty penny as they embark on a much-awaited rebuild.

The start of the Bulls' rebuild, however, shouldn't stop at a LaVine trade. They still have plenty of pieces that could be of help to contending teams, netting them additional draft assets that should help them moving forward.

With that said, these are the other trades the Bulls must pursue as they go all-in on plummeting towards the bottom of the NBA standings in belated fashion, coming after the year of the Victor Wembanyama sweepstakes.

Alex Caruso solves Bucks' perimeter defense woes

Bulls give: Alex Caruso

Bucks give: Pat Connaughton, MarJon Beauchamp, 2027 MIL second-round pick

For all the championship hype surrounding the Milwaukee Bucks, their defense thus far to begin the year doesn't look like it'll get them too far. They have two defensive savants on the interior in Brook Lopez and Giannis Antetokounmpo, but their defense on the perimeter has been lackluster, with the likes of Damian Lillard and Malik Beasley being turnstiles while guarding the point of attack.

As a result, the Bucks have put up the sixth-worst defensive rating in the league through 10 games, allowing 116.0 points per 100 possessions. Simply put, they have been missing Jrue Holiday's exceptional ability to get over screens and funnel ballhandlers towards Lopez's path. But with the Bulls opening up a fire sale, the Bucks may very well have an opportunity to grab someone who could approximate Holiday's impact.

Alex Caruso has been one of the best defensive guards in the league for years, as his ability to shadow shooters on the move as well as his ability to mirror ballhandlers' movements make him quite the defensive presence on the perimeter. Caruso just does all the little things that contribute to winning; he crashes the glass, keeps the ball moving, and he only takes good shots.

The Bucks no longer have the assets to match the Bulls' reported asking price for Caruso last year, but Chicago's ask of two first-round picks for the 29-year old guard should come down as they lose leverage by the day. MarJon Beauchamp should be an enticing prospect for the Bulls to take on in place of a first-rounder, especially when the 23-year old wing is already showing flashes of becoming an impact player for the Bucks.

Heat get DeMar DeRozan as a consolation prize

Bulls give: DeMar DeRozan

Heat give: Kyle Lowry, Nikola Jovic, 2026 MIA first-round pick swap

The Heat, as per usual, are reportedly going to be involved in the Zach LaVine trade sweepstakes. But in terms of trade assets, other prospective LaVine suitors have more to offer the Bulls. Plus, the Bulls may end up asking for Tyler Herro as well, which will give the Heat some pause. Thus, Miami may have to “settle” for a consolation prize in DeMar DeRozan.

DeRozan's skillset doesn't exactly make him an easy player to fit on a contending team; and at age 34, there's certainly risk in bringing him in, especially when he's on an expiring contract and he hasn't exactly been his usual self to begin the 2023-24 season. But if there's a team that could bring out the best in DeRozan, it's the Heat.

Given DeMar DeRozan's contract situation and decline in efficiency to begin the year, the Heat shouldn't overpay for his services; this must be the best offer they put on the table given the risk-reward calculus.

For the Bulls, getting a versatile young forward who could very well develop into a keeper in Nikola Jovic for someone who, more likely than not, will be departing at season's end, could be a huge win. Moreover, getting a pick swap for their troubles may be worth it as well.

Grizzlies take one more swing

Bulls give: Nikola Vucevic

Grizzlies give: Steven Adams, Jake LaRavia, 2026 lottery-protected MEM first-round pick, 2030 MEM second-round pick

The Bulls may not get as much of a return for their players (apart from Zach LaVine) as they would hope; that is how dire the situation has become in the Windy City. Nikola Vucevic, the guy they acquired for Wendell Carter Jr. and the picks that became Franz Wagner and Jett Howard, won't net them anywhere close to the same return.

Vucevic, in this scenario, should still net them a few good assets from the Grizzlies, namely a lottery-protected 2026 first-rounder and former first-round pick Jake LaRavia. For the Grizzlies, Vucevic should help stabilize their offense in Ja Morant's absence; Vucevic is also a solid complement to Jaren Jackson Jr., as he should take care of the glass and tough matchups on the post while Jackson takes care of protecting the rim.