Hypothetical Bulls Trades to Boost Pursuit of 2024 NBA Title

The Chicago Bulls aren't contending for the 2022-23 NBA crown.

If we're being honest, they probably won't challenge for the throne next season, either.

But who wants to abandon hope for next season before this one is even finished? Let's bathe in optimism, instead, as we drum up three possible offseason trades that could push this water-treading team into title contention.

Getting a Paint Protector

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NEW YORK, NEW YORK - DECEMBER 23: Mitchell Robinson #23 of the New York Knicks in action against the Chicago Bulls during the first half at Madison Square Garden on December 23, 2022 in New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Adam Hunger/Getty Images)

The Trade: Ayo Dosunmu (sign-and-trade), Andre Drummond and protected first-round pick to the New York Knicks for Mitchell Robinson

Interior defense has been a challenge for Chicago. It will remain one as long as Nikola Vučević is manning the middle.

The Bulls can make their break this summer, as free agency awaits him. He is a super-skilled player on the offensive end, but Chicago's offense can function without him. And even if it were to sag a bit, the improvements on the defensive end could more than compensate for that.

If Chicago lets Vooch walk, it could target Mitchell Robinson as his replacement. The 7-footer is longer, bouncier and much more active on defense. He also doesn't need a ton of touches—though he wouldn't mind more than he gets in New York—which should make it easier for him to play off of DeMar DeRozan and Zach LaVine.

The Knicks, meanwhile, might feel good enough about their center rotation to sacrifice Robinson for a few long-term assets.

Ayo Dosunmu's defense-first approach would make him a Tom Thibodeau favorite, and the draft pick would give New York another trade chip to throw in a blockbuster deal. Andre Drummond would be an insurance policy in case Jericho Sims isn't ready for regular rotation minutes.

The All-In Option

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CHICAGO, ILLINOIS - FEBRUARY 04: Damian Lillard #0 of the Portland Trail Blazers looks on against the Chicago Bulls during the first half at United Center on February 04, 2023 in Chicago, Illinois. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Michael Reaves/Getty Images)

The Trade: Lonzo Ball, Patrick Williams, Coby White (sign-and-trade), Dalen Terry and three first-round picks to the Portland Trail Blazers for Damian Lillard

If the Bulls are ready and willing to throw caution to the wind—they haven't won a playoff series since 2015, so they should be—they have enough chips to make one major trade.

Plucking Damian Lillard away from a reeling Blazers team would be a fascinating roll of the dice. They've had major point guard problems ever since losing Lonzo Ball to a knee injury last January, and this trade would deliver one of the best point guards in the business.

Is there enough defense between Lillard, LaVine and DeRozan to make this work? That's a fair question, but with this level of offensive firepower, it might be a meaningless one. Chicago could easily have the sprinters needed to win nightly races to 125 points.

While Portland seems unlikely to move Lillard unless he requests it, maybe yet another lost season will finally push the 32-year-old toward a scenery change.

If the Blazers are losing Lillard, that means they're starting over and should seek as many picks and prospects as they can get.

Patrick Williams is a blue-chip prospect, Coby White is an interesting one, Dalen Terry is a wild card and three first-round picks are...well, three first-round picks. Ball would function mostly as a money-matcher, but he could be an impact floor general if he ever gets healthy.

Adding a Two-Way Wing

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CHICAGO, IL - NOVEMBER 07: Chicago Bulls forward DeMar DeRozan (11) guards Toronto Raptors forward O.G. Anunoby (3) during a NBA game between the Toronto Raptors and the Chicago Bulls on November 7, 2022 at the United Center in Chicago, IL. (Photo by Melissa Tamez/Icon Sportswire via Getty Images)

The Trade: Patrick Williams, Coby White (sign-and-trade) and future first-round pick to the Toronto Raptors for O.G. Anunoby

If the Bulls are going to trade their way to contention, they'll have to do something major. Most major win-now moves would almost certainly cost this franchise Williams.

That would be tough for some to take, primarily those who picture the 21-year-old as a Kawhi Leonard-in-training. Since our objective here is upping the competitiveness of next season's club, though, we don't have to fret over just how Williams' ceiling can climb.

Instead, we can drool over the defensive abilities of O.G. Anunoby and dream of his fit alongside Chicago's score-first stars. He's the big-wing stopper this roster so desperately needs, and he happens to also be a solid support scorer who drops a lot of hints about being capable of more on the offensive end.

If Toronto doesn't plan on keeping Anunoby long-term—he can hit free agency in 2024—it might prefer this package. The Raptors could easily envision Williams as a future two-way star, and they could use White to either back up or even replace Fred VanVleet.