Bill Simmons Suggests A 3-Team Blockbuster Trade: Damian Lillard To The Celtics, Jaylen Brown To The Rockets

Bill Simmons thinks Damian Lillard's best chance at a title, outside of Miami, might be with the Celtics and suggested a three-team trade.

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Credit: Fadeaway World

The Damian Lillard saga looks set to dominate this offseason after the superstar guard requested a trade from the Portland Trail Blazers.

Lillard has his eyes set on the Miami Heat, but the Blazers won’t settle for a deal they don’t believe is the best for them and could send him elsewhere. With that being the case, Bill Simmons doesn’t think Lillard will end up in Miami and suggested a blockbuster trade to the Celtics.

“I don’t see a trade other than the Miami trade, which I don’t think is going to happen, that will propel him to some sort of, ‘Oh, now he’s on the cusp,’ unless it’s the Celtics,” Simmons said on his podcast. “Jaylen Brown could sign for this extension in five minutes and this will be moot, but I just keep circling that trade wondering it’s starting to make more and more sense to me.”

When Ryen Russillo wondered if he meant a straight Damian Lillard-Jaylen Brown trade, Simmons put forth a three-team deal.

“Like, I think there would have to be a third team,” Simmons added. “I think Jaylen would have to go to, like, Houston, and then Houston would have to send stuff to Portland, and then Portland would send Dame to Boston.”

This would certainly be an interesting move. The Houston Rockets do have a lot of young assets that the Blazers would be interested in and we have also seen that the Rockets don’t mind having veterans on big contracts after signing Fred VanVleet and Dillon Brooks.

Brown, who averaged 26.6 PPG, 6.9 RPG, 3.5 APG, 1.1 SPG, and 0.4 BPG last season, would become the face of the franchise and he’d reunite with his former head coach Ime Udoka as well.

As for Lillard, it was reported that the Celtics, Clippers, Timberwolves, and Pelicans were among the teams that reached out to the Blazers for a potential trade. If we do exclude the Heat, as Simmons suggested, then the Celtics just seem to be the best option if he wants to win a title. 


Damian Lillard Doesn’t Want To Go The Celtics

The one problem with this scenario, put forth by Simmons, is that Lillard doesn’t want to go there. NBA insider Chris Haynes, who is just about as well connected to Dame as anyone, stated it is safe to say the guard won’t be in Boston. It is a bit odd to rule out the Celtics, but there is probably some good reason why Lillard isn’t too keen to go there.

Jayson Tatum is reportedly trying to recruit him, though, and if it does become clear that there is just no way for him to end up on the Heat, Lillard could change his stance on Boston. He and Tatum would certainly be a formidable duo who would be a major headache to deal with for anyone.

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Gautam Varier is a staff writer and columnist for Fadeaway World from Mumbai, India. He graduated from Symbiosis International University with a Master of Business specializing in Sports Management in 2020. This educational achievement enables Gautam to apply sophisticated analytical techniques to his incisive coverage of basketball, blending business acumen with sports knowledge.Before joining Fadeaway World in 2022, Gautam honed his journalistic skills at Sportskeeda and SportsKPI, where he covered a range of sports topics with an emphasis on basketball. His passion for the sport was ignited after witnessing the high-octane offense of the Steve Nash-led Phoenix Suns. Among the Suns, Shawn Marion stood out to Gautam as an all-time underrated NBA player. Marion’s versatility as a defender and his rebounding prowess, despite being just 6’7”, impressed Gautam immensely. He admired Marion’s finishing ability at the rim and his shooting, despite an unconventional jump shot, believing that Marion’s skill set would have been even more appreciated in today’s NBA.This transformative experience not only deepened his love for basketball but also shaped his approach to sports writing, enabling him to connect with readers through vivid storytelling and insightful analysis.
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