Bulls Trades to Consider After 1st Wave of NBA Free Agency

The Chicago Bulls still plan to compete.

That's the overarching theme to their 2023 NBA offseason.

They conceivably could have pulled the plug on this core, but they invested in it instead. They extended Nikola Vučević, re-signed Coby White and added Jevon Carter and Torrey Craig.

All of those are win-now moves—made by a franchise that isn't necessarily positioned to win now. That's why the Bulls could be active on the trade market, perhaps trying to pull off something like the following three deals.

Building a Big 4 with Dame

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CHICAGO, IL - FEBRUARY 04: Portland Trail Blazers Guard Damian Lillard (0) posts up against Chicago Bulls Forward DeMar DeRozan (11) during a NBA game between the Portland Trail Blazers and the Chicago Bulls on February 4, 2023 at the United Center in Chicago, IL. (Photo by Melissa Tamez/Icon Sportswire via Getty Images)

The Trade: Lonzo Ball, Patrick Williams, Ayo Dosunmu (sign-and-trade), Dalen Terry, a 2024 first-round pick (lottery-protected, via POR), a 2027 first-round pick, a 2029 first-round pick and two pick swaps to the Portland Trail Blazers for Damian Lillard

The Bulls, as you may have heard one time or a million more, have had a point guard problem ever since losing Ball to a knee injury in Jan. 2022. That's why this front office may have done a spit take upon reading the news of Lillard's trade request.

While Chicago did well to pivot toward Carter this summer, Lillard sits several tiers above him and everyone else in this lead guard rotation. Over the past four seasons, he's been a nightly source of 29.4 points (on 45.2/38/90.6 shooting), 7.6 assists and 4.0 threes. He's a true game-breaking talent on the offensive end, and the trickle-down effect on the rest of this roster could make Chicago almost unguardable.

How many defenses have answers for Lillard, Zach LaVine, DeMar DeRozan and Vučević? Not enough to prevent this group from winning nightly races to 120-plus points. The Bulls would have a lot of defensive holes, but their offensive potency could overcome them.

If the Blazers are big believers in Williams (and, to a lesser extent, Dosunu and Terry), this might be enough for them to sign off on the swap.

An Alternate, More Complicated Path to Lillard

AP Photo/Nam Y. Huh

Chicago Bulls guard Zach LaVine, left, looks to pass as Portland Trail Blazers guard Damian Lillard tries to steal the ball during the first half of an NBA basketball game in Chicago, Saturday, Jan. 30, 2021. (AP Photo/Nam Y. Huh)

The Trade: Damian Lillard to Chicago; Zach LaVine to the Houston Rockets; Kevin Porter Jr., Jalen Green, Jae'Sean Tate, Cam Whitmore, a 2024 first-round pick (lottery-protected, from POR via CHI) and a 2028 first-round pick (via CHI) to the Portland Trail Blazers

Because the Bulls have had issues at point guard, and because there happens to be a top-shelf point guard on the market, it makes sense to explore a second path to Lillard. Even one as convoluted as this.

The likeliest outcome to the Lillard sweepstakes is some kind of three- or four-team trade. Those can be tricky to pull off, since everyone needs their back scratched in some fashion, but it's the easiest way to connect Portland with a Lillard shopper. Teams who want Lillard are in win-now mode, meaning they probably don't have the kind of long-term assets the Blazers want. That's where the third team enters the chat.

In this case, it's Houston, which signaled a clear desire to compete this summer by adding several prominent veterans, most notably Fred VanVleet and Dillon Brooks. Maybe that's enough for the Rockets to think they've changed the culture, but perhaps this club is interested in fast-forwarding things even further. In that case, it could be willing to sacrifice some of its young talent for an established star like LaVine.

The Bulls, meanwhile, would lose LaVine and two firsts—though, one would just be a Blazers' pick returned to Portland—to land Lillard. That's a significant cost, but it would allow Chicago to upgrade its star collection without depleting its depth.

Winning the Siakam Sweepstakes

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TORONTO, ON - APRIL 12: Pascal Siakam #43 of the Toronto Raptors battles against Nikola Vucevic #9 and Alex Caruso #6 of the Chicago Bulls during the 2023 Play-In Tournament at the Scotiabank Arena on April 12, 2023 in Toronto, Ontario, Canada. 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 Andrew Lahodynskyj/Getty Images)

The Trade: Lonzo Ball, Patrick Williams, Dalen Terry and a 2027 first-round pick to the Toronto Raptors for Pascal Siakam

If the Bulls want to snag another star, Lillard isn't their only option. Siakam could also be up for grabs.

"Siakam has been certified as the next biggest trade name on the league's unforgiving rumor mill," Yahoo Sports' Jake Fischer reported.

Siakam might be the cleaner fit with this core on paper, since he's a positive contributor at both ends. He's also a wildly productive player in is own right, having just delivered per-game averages of 24.2 points, 7.8 rebounds and 5.8 assists. He should also cost less than Lillard since he's entering the final year of his contract and has "left rival teams with the impression he only intends to sign the extension he's eligible to receive this offseason if he remains with Toronto," per Fischer.

If the Bulls would risk adding him anyway, they could take a huge step forward with this trade. Ball isn't playing next season, and Terry could again struggle to see the floor, meaning the only real rotation change would be the massive upgrade from Williams to Siakam. That could be the kind of change needed to lift Chicago's ceiling high enough to justify keeping this nucleus together.