Damian Lillard may want to join the Miami Heat, but another team has seemingly jumped to the front of the line in trade negotiations with the Portland Trail Blazers in recent days. The Toronto Raptors have convinced the league that they are serious in their pursuit of Lillard, according to Marc Stein, and ESPN's Marc Spears called the Raptors the "hottest name" he's hearing on the Lillard front right now, adding that a deal is expected to come before Portland's media day on Oct. 2 and that Lillard, despite his desire to play for the Heat, would show up and play for the Raptors.
Lillard initially requested a trade in July, and agent Aaron Goodwin made it clear that "he wants to play in Miami" in Kawhi Leonard in the 2018 offseason despite his long reported plan to land in Los Angeles. Leonard ultimately did join the Clippers in the 2019 offseason, but not without winning a championship in Toronto first.with the Miami Herald's Aaron Goodwin. The Raptors, however, have a history of trading for superstars with their heart set on on another destination. Toronto landed
Lillard's circumstances are very different than Leonard's were. Leonard was on an expiring contract. Lillard has three guaranteed seasons left on his deal, giving Toronto a bit more time to put a winner around him. Of course, Lillard is 33 years old. Leonard was still only 27 when the Raptors acquired him. Lillard's age would put significant pressure on the Raptors to put a winner around him quickly.
It is not clear what exactly Toronto would give up in a deal for Lillard, though there are two likely centerpieces. Scottie Barnes would likely be Portland's preferred choice. The 2022 Rookie of the Year would give the Trail Blazers a long-term forward to pair with young guards Scoot Henderson and Shaedon Sharpe. Of course, the Raptors were reportedly unwilling to swap Barnes for Kevin Durant last offseason, so they may not be willing to give him up for Lillard. Even if they were, his rookie-scale contract would require so much extra money to match salaries on Lillard that a deal could get complicated.
The other option is OG Anunoby, a more proven forward that is reportedly looking for more opportunities as a ball-handler. Portland could theoretically provide him those chances, and his defense and shooting would pair well with Henderson and Sharpe. Anunoby is on an expiring contract, so Portland would have to feel confident in its ability to re-sign him, but wings of his caliber are rarely available in trades.
No deal is imminent, but Blazers media day is around the corner. If Portland truly wants to move Lillard before training camp begins, the time to make a deal is now. Toronto may be in the lead for now, but there is still time for another team to jump into the fray and land the superstar point guard.