According to Shams Charania of The Athletic and Stadium, there is a belief in the NBA that the Portland Trail Blazers could secure "several" first-round picks in a trade with the Miami Heat for Damian Lillard.

During his appearance on the Pat McAfee Show, Charania revealed a potential "framework" in which the Portland Trail Blazers could obtain three or possibly even four first-round picks. The proposed trade involves the Heat offering two first-round picks while a third team acquires Tyler Herro, contributing at least one additional first-round pick to the Blazers.

According to a report by Aaron Fentress of The Oregonian, the Trail Blazers are aiming to acquire four first-round picks and "two quality players" in any potential Damian Lillard trade. This resembles the framework of the trade that sent Donovan Mitchell to the Cleveland Cavaliers last offseason, where the Utah Jazz received Lauri Markkanen, Collin Sexton, Ochai Agbaji, three first-round picks, and two pick swaps.

Since then, the market dynamics have shifted, as demonstrated by the Phoenix Suns not giving up an unprecedented haul for Kevin Durant when he joined the Brooklyn Nets. While the package of Mikal Bridges, Cameron Johnson, and several picks was decent, it fell short of the expectations set by previous offseasons.

There are other important considerations to keep in mind, particularly Lillard's age, as he is nearing 33, and the significant amount of remaining salary on his contract, which amounts to $216.2 million. Even with projected increases to the salary cap, paying Lillard $63.2 million in the 2026-27 season might not be seen as a wise investment.

Moreover, Lillard has been explicit through his agent about his preferred destination.

Due to his contract size and the limited number of playoff contenders in need of a star point guard, the market for Lillard was already expected to be narrow. By publicly revealing his preferred destination, the chances of a bidding war appear even slimmer.

When trading a star player, especially one who holds such significance in franchise history, the Blazers are likely to emerge as the losers in the deal.

However, securing multiple first-round picks would provide the front office with the opportunity to lay the foundation for a rebuilding phase.