"Never trading with those f****g guys": NBA insider reveals Joe Cronin's miffed take after botched Damian Lillard trade with Heat

During the 2023 offseason, the biggest splash of the summer was Damian Lillard being traded from the Portland Trail Blazers to the Milwaukee Bucks. A year removed from the blockbuster deal, one insider detailed how one franchise derailed its chances of landing the star point guard.

When Lillard first became available, the Heat were one of the most interested teams in signing him. Their package was headlined by former Sixth Man of the Year Tyler Herro and multiple first-round picks. As we know, the Trail Blazers opted to decline this offer in favor of the package they got from the Bucks.

While on his podcast, Bill Simmons reflected on whether the Blazers made the right decision in regards to the Damian Lillard trade. He also brought up how the Heat's behind-the-scenes antics resulted in a deal never coming about.

"Miami and their whole little annoying media machine that they have f***** up that Portland situation," Simmons said. "To that point that Joe Cronin and the Portland people were like, 'We're never trading with those f***** guys.'"

In return for Lillard, Portland received Deandre Ayton, Jrue Holiday, one first-round pick and two pick-swaps. The front office was able to recoup even more assets when they re-routed Holiday to the Boston Celtics for Robert Williams, Malcolm Brogdon and two more first-round picks.

As for the Heat, they later made a trade for Terry Rozier to fill their need at the point guard position.

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Damian Lillard shares ad for new signature shoe ahead of second season with Milwaukee Bucks

After being the blockbuster trade of the summer, Damian Lillard did not live up to expectations in Year 1 with the Milwaukee Bucks. Along with dealing with the madness of switching teams, the eight-time All-Star was going through things in his personal life.

Heading into his second year with the Bucks, Lillard seems focused on having a bounce-back year. Earlier this week, he posted a motivational ad for the latest addition to his line of signature shoes. The commercial talks about always moving forward and shows a glimpse of the new sneaker.

Damian Lillard was an All-Star in 2024 after averaging 24.3 points and 7.0 assists. However, the duo of Lillard and Giannis Antetokounmpo did not have the playoff success many expected from them. After securing the No. 3 seed in the Eastern Conference, the Bucks were upset in the first round by Tyrese Haliburton and the Indiana Pacers (with Antetokounmpo sidelined with a calf injury).

Heading into Year 2 in Milwaukee, Lillard has a chance to contend for a championship. He and Giannis are still a top duo in the league, there likely won't be another midseason coaching change and the front office made improvements to the roster. It won't be an easy journey, but this duo certainly has the talent to get it done on the game's biggest stage.