Heat Not Trading for $176 Million Star Called ‘Biggest Regret’

“In addition to justifying cap-clearing moves like allowing Gabe Vincent and Max Strus to walk, a Lillard acquisition probably would have helped the Heat lighten Jimmy Butler’s workload and produced a finish higher than 21st in offensive efficiency,” Hughes wrote in an April 16 story.

Hughes elaborated further on the consequences that came after the Heat did not acquire Lillard.

“Had they landed Lillard, it obviously would have prevented Jrue Holiday from winding up with a Boston Celtics squad that won more games than any other team. Add to that the possibility of Miami sending out Tyler Herro, who missed half of the season due to injury, and missing out on Dame gets more painful all the time.

“Lillard to Miami seemed like a foregone conclusion until it wasn’t. The Heat will be thinking about what could have been for a long time.”

Instead, the Portland Trail Blazers traded Lillard to the Milwaukee Bucks. However, their season didn’t exactly go to plan either. Lillard is in the third year of a four-year, $176 million contract, and he also has a two-year extension when that contract ends.

Damian Lillard Did Not Practice With Bucks

Lillard did not have a great season with the Bucks. In his first season with Milwaukee, he averaged 24.3 points, 7.0 assists and 4.4 rebounds. At the same time, he shot 42.4% from the field and 35.4% from three.

With Giannis Antetokounmpo out to start their series against the Indiana Pacers, Doc Rivers revealed that Lillard also didn’t practice on April 16 due to injury.

Rivers gave the full details to reporters, per Eric Nehm’s X account.

Lillard’s injury issues, knowing how many miles are on his tires, along with his performance for the Bucks can be a comfort for Miami. It can make the argument that maybe the Heat were right to not sell the farm for him when they had the chance. He’ll be 34 in July, and he’ll likely be paid upwards of $58 million during the 2026-27 season.

Stephen A. Smith Believes Bucks Should Trade Damian Lillard

ESPN’s Stephen A. Smith is not optimistic about the Bucks’ chances in the first round. So much so that he believes a trade is in order if they lose to Indiana.

“With or without Giannis, Indiana is winning this series,” Smith said on the April 14 episode of ESPN’s “NBA Countdown.” “When that happens, I think the Bucks should take a strong look at using the asset, i.e. Damian Lillard, and moving him from Milwaukee this summer.”

If the Bucks agree with Smith on that front, perhaps a Lillard to trade Miami wouldn’t be out of the question after all. Better yet, after the season he had had, the Heat could get him for cheaper than what they would have had to in 2023.

The Bucks will likely be hesitant to trade Lillard to an Eastern Conference rival, but if they lost in the first round for the second consecutive year, they have to think about making some changes.