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Damian Lillard rumors: Comparing potential Raptors, Heat trade packages

Andrew Hanlon
Andrew Hanlon

Rip City Project

Damian Lillard, Portland Trail Blazers Mandatory Credit: Soobum Im-USA TODAY Sports

The Damian Lillard rumors are beginning to trickle in a little faster now as NBA teams inch toward training camp, and the latest two are the juiciest. First, it was reported on Sept. 18 by ESPN’s Marc Spears that an unnamed Eastern Conference team has been in talks with the Portland Trail Blazers over Lillard.

The next day, Matt Moore of The Action Network confirmed on the Locked On NBA Podcast (3:45 mark) who that team might be: the Toronto Raptors.

A mystery team inserting itself into the Lillard rumors gives the Blazers some additional leverage. Assumedly, general manager Joe Cronin has been using that in his negotiations with the Miami Heat.

Now that the Raptors are officially involved – or even if they were at some point – things swing a bit in the Trail Blazers favor. Maybe Toronto’s offer is really good, maybe it’s totally underwhelming. Either way, Cronin has some leverage of his own now.

He can go back to the negotiating table with Heat President Pat Riley and say, “I have another team that’s interested in Dame. Increase your offer, either to match theirs or beat it, or we’re moving forward with Toronto.”

Cronin can now pit the Heat and Raptors – or perhaps other teams, according to Moore – against each other in a bidding war. That raises the most important question of all: Which franchise has the trade assets to potentially come out on top and land Damian Lillard?

Can the Heat or Raptors offer the Portland Trail Blazers a better Damian Lillard trade package?

The Miami Heat’s trade assets

Miami’s offer has already been discussed extensively, as the Heat have been involved in the Lillard rumors since they began in July.

Riley has reportedly put an offer on the table of three or four first-round picks/pick swaps, a young player and potentially a few second-rounders. One of those firsts would come from a third team, as the Blazers have no desire to add Tyler Herro, another defensively-challenged guard who doesn’t fit the franchise’s future plans.

Miami’s list of realistic and desirable trade assets includes the following:

  • Herro: 23 years old, entering the first year of a 4-year, $120 million contract
  • Caleb Martin: 27-year-old forward, $6.8 million salary in 2023-24, $7.1 million player option in ’24-25
  • Jaime Jaquez Jr., forward, 18th overall pick in 2023 NBA Draft
  • Nikola Jovic, forward, 27th overall pick in 2022 NBA Draft
  • Haywood Highsmith, wing, 26 years old
  • Kyle Lowry’s $29.6 million expiring contract
  • First-round picks in 2028, 2030
  • First-round pick swaps in 2027, 2029
  • Second-round pick via LAL in 2026

The Blazers have been adamant about getting everything they can from the Heat, which means Riley would have to part with a significant number of these assets to land Lillard.

Scottie Barnes is an attractive trade asset the Toronto Raptors have to offer for Damian Lillard.
Scottie Barnes, Toronto Raptors (Photo by Dustin Bradford/Getty Images)

Toronto Raptors trade assets

Raptors President Masai Ujiri seems to find a way to sneak into dilemmas such as this.

First, it was trading for Kawhi Leonard despite not being on the list of the former San Antonio Spurs star’s preferred destinations. But it worked – Kawhi led Toronto to the 2019 NBA Championship.

Could Lillard be Ujiri’s next significant gamble?

The Raptors desireable, potentially attainable assets include:

  • Scottie Barnes, 2021-22 NBA Rookie of the Year
  • O.G. Anunoby, 26-year-old forward, $18.6 million salary in 2023-24, $20 million player option in 2024-25
  • Gary Trent Jr., 24-year-old guard, $18.6 million salary in 2023-24, unrestricted free agent in 2024-25
  • Gradey Dick, wing, 13th pick in 2023 NBA Draft
  • Precious Achiuwa, 23-year-old center, restricted free agent in 2024
  • Pascal Siakam, two-time All-NBA, $37.8 million expiring contract
  • First-round picks in 2026, 2027, 2028, 2029, 2030
  • Second-round picks in 2026, 2027, 2028, 2029, 2030
Can the Heat or Raptors provide the Portland Trail Blazers with a better Damian Lillard trade package?
Damian Lillard, Portland Trail Blazers (Photo by James Gilbert/Getty Images)

Which team could provide the Portland Trail Blazers with a better Damian Lillard trade package?

In theory, the Raptors could give Portland more for Lillard. In theory.

In actuality, the answer isn’t so straightforward.

There’s a zero chance Toronto is willing to trade Barnes, Siakam or Anunoby. If the goal is to acquire Lillard and go win an NBA title, why would the Raptors part with their best players? And if the Blazers’ goal in sending Dame packing is to rebuild, would they even want Siakam or Anunoby?

Still, there are pieces that would make Toronto an attractive trade partner. Bringing Trent Jr. back to Portland isn’t the worst idea. Dick, as an underrated playmaker, athlete and competitor in addition to being a 6-foot-8 wing and a sniper from deep, would fit in perfectly with the Blazers current young core and youth movement.

Achiuwa is a still-developing, athletic, undersized center who’s already proven to be a solid rotation big, something Portland could certainly use. And the Raptors have those draft picks – five firsts and five seconds available.

Miami, meanwhile, would need to find a third team to facilitate a trade, has less attractive picks and young players than Toronto and has already played hardball with the Blazers for two-plus months.

The Raptors have more attractive assets than the Heat; the question is, which of them would they be willing to part with? And if it’s not enough for Cronin, could the threat of a legitimate Toronto offer at least force Miami to bring more to the negotiation table?

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.