Bulls Falling Behind in Race to Trade for Blazers’ Damian Lillard: Insider

Damian Lillard, Chicago Bulls

Getty Damian Lillard #0 of the Portland Trail Blazers.

The Chicago Bulls’ rumored pursuit of Portland Trail Blazers star Damian Lillard may wind up being shortlived. While Chicago was always considered a long shot, a new front-runner has emerged, putting their standing in the ongoing talks in jeopardy.

“Everybody’s waiting about Miami Heat. … And it’s just — everything I’m hearing is really really quiet there,” Andscape’s Marc J. Spears said September 25 on ESPN’s “NBA Today.” “[The] Blazers are continuing to talk to other teams — where I’ve heard the likes of Chicago and Milwaukee and even Philadelphia. … Even though [the] Chicago thing’s kind of waning a little bit. But the hottest name [of interest] that I’m hearing right now is the Toronto Raptors.”

PHLY Sports’ Kyle Neubeck reported on September 21 that Chicago was exploring “multi-team” deals involving two-time All-Star Zach LaVine with designs on ultimately landing Lillard from Portland.

But Toronto has surged to the front of the pack of potential suitors, Spears said, with a track record to back it up.

Raptors president Masai Ujiri traded for Kawhi Leonard in 2018-19 despite the latter’s well-known intent to land with a team in his hometown Los Angeles the following offseason. Leonard did indeed leave, signing with the LA Clippers that summer after winning the NBA Finals.

Ujiri also worked with Lillard’s agent, Aaron Goodwin, who also represents Bulls star DeMar DeRozan, and worked with the Raptors executive when the Raptors traded the latter to the San Antonio Spurs for Leonard. The Goodwin connection — with DeRozan a potential reason Lillard could be open to a trade to Chicago — also leaves open another possibility.

Raptors Could Be Driving Up Price on Damian Lillard Trade

“Either A) the Raptors’ interest in Lillard is genuine,” The Ringer’s Kevin O’Connor said on “The Mismatch” on September 25. “Or B) He’s [Ujiri] trying to do a solid for Goodwin and Dame.”

O’Connor noted his belief that the Raptors’ interest is real. But how real is still unclear.

“The Raptors’ interest in Portland’s all-star guard is real, albeit ‘a bit overstated at this point,’ wrote Josh Lewenberg of TSN on September 25 citing “multiple” sources with knowledge of the ongoing situation.

Under Ujiri, Toronto has developed a reputation as a shrewd trade partner, willing to let players walk rather than accept a trade they don’t view as worthy. Raptors star Pascal Siakam is a player whom many expected to be moved this offseason as he heads into the final year of his contract, only for him to remain on the roster despite talks with the Atlanta Hawks.

There is also the growing possibility that the Bulls’ aim has not changed, but rather their preferred trade target has.

Bulls Linked to Heat’s Tyler Herro

In the wake of the rumored interest in Lillard, the Bulls are also one of the four teams said to have an interest in Heat star Tyler Herro, according to Jake Fischer of Yahoo Sports. Herro who would be redundant on the Blazers’ roster and is ahead of their current timeline. He is nearly five years younger than LaVine and is on a contract that will cost roughly $58 million less over the next four years.

“If Portland ultimately does business with Miami, the Jazz — as well as the Bulls, Hornets and Nets — are considered a team interested in landing Tyler Herro from the Heat,” Fischer wrote on September 22.

And, if Chicago can somehow include Lonzo Ball in the deal instead, Herro and LaVine could share the floor. Herro could already potentially play point guard in Miami if no trade occurs.

The defense would be a concern, though a top-5 unit did not get the Bulls anything last season.