Here’s a four-team deal that brings Lillard to Miami and sends Herro to a conference rival

The Brooklyn Nets, Chicago Bulls and Utah Jazz have been among the reported teams interested in acquiring Tyler Herro in a multi-team trade that brings Damian Lillard to the Miami Heat, but a new team has emerged as a potential partner.

Sources told HoopsHype that the Toronto Raptors have “expressed exploratory interest in acquiring Herro as part of multi-team trade talks between the Blazers and Heat involving Lillard.” The Raptors make a lot of sense for Herro and as a trade partner when considering the assets that they could include in a larger deal, Herro’s skillset and Toronto’s team needs.

There are several iterations of a potential trade package involving the Heat, Trail Blazers and Raptors, but it would also make sense for Pascal Siakam to be included in exchange for Herro. The issue is that, while Siakam is a very good player, he’s 29 and doesn’t make sense with Portland’s timeline. So that means we’re getting a fourth team involved to take Siakam and send a younger player back to Portland who fits the Scoot Henderson development window.

Four-team trades can get very complicated, but if the Atlanta Hawks — a rumored Siakam suitor — would be willing to trade 25-year-old forward De’Andre Hunter to Portland, there’s the foundation of a deal that could work.

Heat get: Lillard
Blazers get: Hunter, Bogdan Bogdanovic, Precious Achiuwa, Miami’s unprotected first-round picks in 2028 and 2030
Raptors get: Herro, Duncan Robinson
Hawks get: Siakam

Where this framework could fall apart is in the draft compensation. Portland would push for at least one more first-round pick (that Miami could potentially provide by adjusting protections owed to a 2025 first-round pick owed to Oklahoma City) and Toronto could push Atlanta to send picks in exchange for Siakam. But if everyone can agree on the draft compensation, this could be a winning deal for every team involved.

Let’s start with the Blazers, who would be adding a young forward in Hunter that specializes in defending big wings, provides needed size at 6-foot-8, 225 pounds and has shot an encouraging 36% from 3-point range over the last two seasons. Hunter and recently re-signed Jerami Grant could form a versatile forward tandem that the Trail Blazers were missing for much of Lillard’s tenure. Portland could begin the post-Lillard era with a starting lineup of Henderson, Shaedon Sharpe, Hunter, Grant and the 23-year-old Achiuwa, with Anfernee Simons, Bogdanovic and Matisse Thybulle coming off the bench.

As for the Raptors, they address their need for shooting with Herro and Robinson, and Herro gives them a secondary playmaker to run the offense alongside point forward Scottie Barnes. Herro is a career 38% 3-point shooter and developing passer who has averaged 20 points over the last two seasons. He’s a bucket-getter who would immediately help loosen up Toronto’s half-court offense that often stalled last season.

For the Hawks, they add the player they’ve been tied to the most this summer in Siakam, who could form a threatening trio alongside Trae Young and Dejounte Murray. And the Heat, obviously, end up with Lillard.

Much easier said than done, but when scanning the league for trade ideas that bring Lillard to Miami, it often unspools in something similarly complicated.