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Trail Blazers demanding four first-round picks, two quality players for Damian Lillard

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James Foglio
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James Foglio Sports Editor

James is a Basketball Insiders contributor. He earned his bachelor's degree in English and Creative Writing from Southern New Hampshire University. James enjoys watching sports and helping gamblers win money.

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Sports Editor

Updated07 Jul 2023

Portland Trail Blazers demanding four first-round picks, two quality players for Damian Lillard

The Portland Trail Blazers are seeking four first-round draft picks and two quality players in a Damian Lillard trade. For the organization to receive such compensation in a package, a three-team trade is the most logical. The seven-time All-Star prefers a trade to the Miami Heat.

“[Agent Spencer] Goodwin added that in no way does he expect the Blazers to accept a marginal return for Lillard,” wrote Aaron Fentress of The Oregonian. “But at this point, the Blazers must be proactive in reaching a deal with Miami because he doesn’t believe other teams will pursue Lillard.”

Per a few NBA betting sites, the Portland Trail Blazers hold 27th-ranked odds to win next season’s championship in 2024. Sportsbooks are showing better odds for the Oklahoma City Thunder, San Antonio Spurs, and Houston Rockets.


“I don’t think another team would do a deal like that knowing everything that’s going on,” Goodwin said. “But if they do, then they don’t know Dame.” The Los Angeles Clippers, Minnesota Timberwolves, and New Orleans Pelicans are also interested in trading for Lillard.

Instead of the Boston Celtics targeting the 11-year veteran, the front office is working on offering Jaylen Brown a supermax extension. Even if the C’s were interested, Lillard would not want to play in Beantown. “He’s not doing Boston,” TNT NBA Insider Chris Haynes said on “The Dan Patrick Show” last month.

Portland Trail Blazers are asking for four first-round draft picks, two quality players in a Damian Lillard trade; Would the Miami Heat have to give away Tyler Herro and Bam Adebayo?

On Tuesday, Trail Blazers G.M. Joe Cronin turned down Miami’s trade proposal involving Tyler Herro and multiple draft picks. “Portland is ‘not impressed’ with the Heat’s trade offer for Damian Lillard, which could lead to a deal elsewhere now,” said ESPN’s Adrian Wojnarowski. “While Damian Lillard prefers Miami, Portland needs ‘maximum value’ in any trade.”

Unfortunately for Heat fans, it seems the only way for Miami to acquire Lillard would be to send Herro and Bam Adebayo to Portland. As a result, losing these two said players will gut the roster, especially if Lillard struggles to stay healthy in future seasons. The risk does not outweigh the reward. Four first-round draft picks are a lot as well.

However, the Chicago Bulls could be that third team in a trade if a deal materializes.

In 58 starts with the Trail Blazers in the 2022-23 season, Lillard averaged a career-high 32.2 points per game, along with 4.8 rebounds, 7.3 assists, and 36.3 minutes per game. The seven-time All-NBA member also shot a career-high-tying 46.3% from the floor and 37.1% outside the arc.

In July 2019, Lillard signed a four-year, $176 million Designated Veteran Player extension with Portland. Last offseason, the guard inked a two-year, $121.77 million extension with the club. His 2024-25 player option worth $48.79 million was exercised as part of his new contract extension.

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