If we learned anything this NBA offseason, it is that nobody wants to extend Pat Riley's winning time.

The Miami Heat executive spent the summer believing Portland Trail Blazers point guard Damian Lillard would fall into his lap, joining Jimmy Butler and Bam Adebayo on a team that could deliver him a 10th championship ring. Instead, the rival Milwaukee Bucks stole Lillard from under his nose, pairing the seven-time All-NBA selection with two-time MVP Giannis Antetokounmpo and disrupting Riley's best-laid plans.

Lillard requested a trade as free agency opened. His agent, Aaron Goodwin, publicly acknowledged, "He wants to play in Miami. Period," warning other suitors, "It’s not fair to a team to allow them to engage in a negotiation that could be futile in the end," even though Lillard's $176 million contract runs through 2027. The NBA went so far as to alert all 30 teams that Lillard faced discipline if his public negotiating persisted.

Riley proceeded accordingly for the past three months, reportedly leaving only an offer of Tyler Herro and two first-round draft picks on the table for Lillard. The Heat could have sweetened the deal, adding some combination of Nikola Jović, Jaime Jaquez Jr. and a third first-round pick. Why pay more, the thinking went, when all other teams were tempering their offers with the reality that Lillard might not want to play for them?

Only, things changed this past week, when the Toronto Raptors emerged as a serious threat to land Lillard among several other interested teams, ESPN's Marc J. Spears reported. "The Blazers never re-engaged the Heat before accepting this offer from the Bucks," according to the Miami Herald's Anthony Chiang.

Milwaukee's winning bid: Jrue Holiday, Grayson Allen, a 2029 first-round draft pick and a pair of first-round pick swaps. Regardless of who is to blame for the breakdown in negotiations between Miami and Portland, whether spite played any role, or if the Bucks felt the Heat's best offer still was not enough, Riley whiffed.

The 78-year-old is not used to whiffing. Riley coached the Los Angeles Lakers to five championships in the 1980s, an era chronicled in HBO's recently canceled "Winning Time." As Miami's lead executive, he paired Dwyane Wade with Shaquille O'Neal for another title and Wade, LeBron James and Chris Bosh for two more. His latest coup — drafting Adebayo and swapping Josh Richardson for Butler — resulted in a pair of Finals appearances over the past four years, and Lillard was supposed to be the missing piece to finish the job.

As the Heat waited on Lillard, they let two starters from this past season's Finals team — Gabe Vincent and Max Strus — walk in free agency for a combined $25 million in 2023-24. Not only that, one of their primary competitors in the East obtained Lillard. The Bucks swept Miami in a first-round playoff series en route to the 2021 championship, and the Heat returned the favor on their path through the conference last season.

In other words, the Bucks are better, and the Heat are worse. In the immediate aftermath of Wednesday's trade, BetMGM bumped Milwaukee ahead of Boston for the best odds to win the East this coming season, and Miami dropped below the Philadelphia 76ers and Cleveland Cavaliers. The Heat are long shots again.

Equally concerning for Riley, Lillard could make Antetokounmpo more amenable to re-signing in Milwaukee. Antetokounmpo informed The New York Times last month, "I'm not signing" an extension beyond 2025 if the Bucks do not recommit to helping him win another championship. There was reportedly mutual interest between Antetokounmpo and the Heat in a joint venture before he signed his contract extension in 2020.

Milwaukee's acquisition of Lillard marked a significant step toward earning another long-term endorsement from Antetokounmpo. If his availability was Miami's backup plan for Lillard, that ship might have also sailed.

Riley will not go quietly. There are other quick fixes and slow plays to pursue. Miami is expected to pursue Holiday from the Blazers, sources told Yahoo Sports. He would be an ideal fit for Heat culture, although Portland might make them pay the Lillard price for a lesser return. James Harden is available from the Sixers for another hefty price and a worse fit. Donovan Mitchell may soon be available from the Cavaliers. Joel Embiid and Luka Dončić are next on the list of superstars who could become disgruntled ahead of their 2026 free agencies.

Except, Miami's roster is built for now. Butler is 34 years old. He is approaching 30,000 combined regular-season and playoff minutes. Kyle Lowry and Kevin Love, both of whom are currently slotted in important roles, are even older. The Heat owe Butler, Adebayo, Herro and Duncan Robinson a total of $130 million in the 2025-26 season — 90% of the projected salary cap — and the Lillard trade laid bare Herro's value.

Finding a star is not easy, especially one who wants only to be traded to your team, and securing one becomes more difficult when the new collective bargaining agreement goes into full effect next year. Nobody is going to hand Riley his next ring. He will have to earn it, and that requires paying full price.