Bill Simmons offers a trade proposal that sends DeRozan and Caruso to Miami for Herro landing in Chicago

Bulls leaders 

Both Deebo and Alex have maintained their leadership spots in Chicago this season. The All-Star swingman is averaging 22.3 points, 5.3 assists, and 4.1 boards in 49 games. Meanwhile, the do-it-all vet in AC has 9.9 points, 3.8 boards, and 2.8 assists while enjoying the best three-point shooting efficiency of his career at 40.4 percent.

On the other hand, Herro remains one of the premiere microwave guards of the league. He is averaging 20.8 points, 5.3 boards, 4.3 assists, and has a career-high 40.3 percent rate from downtown.

Herro's current contract offers long-term security that allows him to earn until the 2026-27 season. However, this is completely different in the case of Deebo who holds an expiring deal. AC for his part, will get paid until next season.

Assessing Simmons' trade proposal 

To complete this hypothetical trade, the Heat is required to match DeMar and Alex's salaries. Nevertheless, a potential deal that includes all of the mentioned players will only signal that the Bulls are committing to rebuilding. 

Acquiring Herro offers a thrilling idea as he will form a spectacular young backcourt tandem with Coby White, and the attached first-round pick coming from Miami will be crucial in the team's reconstruction plans moving forward.

As it is, this is the move that the Heat will commit out of desperation to go all in for their championship. While there is plenty of skepticism on the redundancy of play style between Deebo and Jimmy Butler, Miami will still surely love to have Carushow at their side as his skill sets, hustle, and defense perfectly embody their proud Heat Culture and what head coach Erik Spoelstra desires to have for a player.

But by acquiring DeMar, they have the choice to either re-sign him this offseason or look for other stars whom they can attract in free agency with the flexible cap space that they saved.

With less than 24 hours left on the clock before we reach the trade deadline, it is yet to be seen if this trade proposal by Simmons will materialize into reality for both the Bulls and the Heat.