Despite initial reports linking Damian Lillard to Miami once again, the Heat were not interested in finally making the partnership happen.
(Photo via Imagn Images)

Remember the infamous 2023 summer-long drama of Damian Lillard’s trade request demanding “Miami and Miami only?” Well, Portland Trail Blazers’ general manager Joe Cronin was determined to waste an entire offseason for his franchise superstar. He also allowed his stubbornness to make negotiations with the Miami Heat as painful as possible.

Ultimately, Lillard was shipped to the polar opposite of living in sunny South Florida. He got traded to the Milwaukee Bucks.

Not only did that Milwaukee experiment not work, but they cut ties with Lillard earlier this summer in a historic waive-and-stretch. Now Lillard had the opportunity to embrace the flexibility of being an unrestricted free agent. He was holding the cards for his next destination.

According to Marc Stein, he reported shortly after the Bucks buyout that the Heat had “serious interest” in finally adding the top-75 NBA talent.

Despite those initial reports and fan reaction, lining up to the overdue Lillard pairing with Miami, the interest from the Heat’s side was never as strong as it appeared. This was according to Sam Amico of HoopsWire.

Considering he is still getting paid his max contract from Milwaukee, it had been speculated that Lillard could sign somewhere for a bargain veteran minimum deal. He finished the 2024-25 season with averages of 25 points, 7 assists, and 4.7 rebounds on 45% shooting.

That somewhere wound up being a very familiar destination for the nine-time NBA All-Star. And it wasn’t at the discounted price that was expected.

Damian Lillard returned to the place it all began in a reunion with the Portland Trail Blazers.

On Thursday afternoon, lead NBA insider Shams Charania broke the internet with the breaking. It featured Lillard choosing to return to the Portland Trail Blazers.

After being drafted by the organization in 2012 and repping the Blazers jersey for 11 seasons, Lillard inked a three-year $42 million agreement. He was coming back in what may be his final NBA contract in his late 30’s.

BREAKING: Nine-time NBA All-Star Damian Lillard is finalizing a three-year, $42 million contract to return to the Portland Trail Blazers, sources tell ESPN. Deal is expected to include a player option in 2027-28 and a no-trade clause. A storybook reunion home for the 35-year-old. pic.twitter.com/mm1uUtMgO6

— Shams Charania (@ShamsCharania) July 17, 2025

The Blazers legend was able to make amends with Joe Cronin from his messy 2023 trade request, and he was able to fetch much more than a minimum contract. It was a perfect situation to be back home in Portland for him and his family.

Lillard will now earn $70 million combined for the 2025-26 campaign, combining both salaries from the Bucks and Blazers.

Shortly after the signing with Portland was announced, reports followed. There were plenty of suitors and contenders showing interest in the guard for the minimum or mid-level exception. The Boston Celtics were a team that was widely linked to him.

Additionally, it was reported that Lillard had no intention of leaving the Bucks. He wanted another shot at competing for a title alongside Giannis Antetokounmpo.

That was before Milwaukee decided to go in another direction.

As for the Heat, their window to capitalize on Lillard’s interest to come to Miami passed them by. They had a prime opportunity to double down on a Jimmy Butler-led championship window. This followed their last Finals run in 2023 to bring Lillard into the fold— but to no prevail.

Similar to Dwyane Wade’s farewell years in his end-of-career Miami return, the Blazers get their own version of that. This spans the next three years with arguably their greatest player in franchise history.

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