When Damian Lillard finally requested a trade out of Portland, his preferred destination was the Miami Heat. Trail Blazers general manager Joe Cronin decided to meet Lillard halfway, finding a team that gave him a legitimate shot at his first title while also balancing the best return possible.
The Blazers dodged a bullet by sending Lillard to the Milwaukee Bucks instead of Miami.
The headliner in any package coming back from the Heat likely would have been Tyler Herro. Sure, he made his first All-Star appearance this year, averaging 23.9 points, 5.5 assists, and 5.2 rebounds. And at 25 years old, another level may still be unlocked.
But ESPN's Bobby Marks expects Herro to sign a three-year, $149.7 million extension. He's good, but he's not that good.
Thankfully, the Blazers aren't stuck with Tyler Herro’s looming extension
To make matters worse, should Herro make an All-NBA team next season, he's eligible for a five-year, $380 million supermax contract. That's an unlikely outcome but not entirely out of the question, which forces Miami's hand.
Teams should be hesitant to commit $50 million a year to borderline All-Stars like Herro, especially under the new CBA. Miami barely made the playoffs in the underwhelming Eastern Conference, only to be swept by the Cleveland Cavaliers; this shows that they can't realistically build a contender with Herro as one of their top players.
The Blazers' backcourt is already a headache, and adding Herro into the mix would further complicate things.
To a lesser extent, the Blazers face a similar predicament with Anfernee Simons, whose contract is set to expire after 2025-26. Both are great players, but their respective teams risk limited ceilings by making them one of their top-paid players.
The gap between trade packages is only getting wider
The Heat also could have acquired another star who wanted to pair up with Lillard and Bam Adebayo in Miami, which is already a popular landing spot. Their success would have diminished the value of any draft picks returning to Portland.
Meanwhile, Milwaukee's future picks and swaps are suddenly some of the most coveted assets in the league. Cronin's gamble against the Bucks was harder to understand at the time, as any team with Giannis Antetokounmpo is automatically a playoff contender.
But their downfall and Giannis' potential departure now puts the Blazers in a prime position to either land a top pick or facilitate a blockbuster trade.
While Miami's potential trade package keeps depreciating, Milwaukee's looks increasingly like a win. And with Herro's looming extension, the gap between the two packages that Cronin could have taken becomes even wider.