Heat's failure to trade for Damian Lillard has only gotten painfully worse

Things started going downhill a long time ago.
Milwaukee Bucks v Miami Heat - Emirates NBA Cup
Milwaukee Bucks v Miami Heat - Emirates NBA Cup | Megan Briggs/GettyImages

Although this Miami Heat season has been a disaster, the root cause of their struggles goes back further than you might think.

There’s a strong argument to be made that the true downfall of the Heat began in September of 2023, when Pat Riley struck out on Damian Lillard.

Rewinding to the offseason following Miami’s incredible 2023 NBA Finals run, the team was just one piece away from finishing the job. Granted that Tyler Herro missed virtually all of the 2023 postseason due to a fractured hand, it was clear that Jimmy Butler needed help. Not from Bam Adebayo or undrafted players. The Heat needed another offensive superstar. 

After years of failing to acquire big names like Kevin Durant, Donovan Mitchell and James Harden, Riley was given another chance to maximize the Butler era when Lillard requested a trade from the Portland Trail Blazers and asked specifically to be sent to the reigning Eastern Conference champion Heat.

After months of failed negotiations between Riley and Blazers general manager Joe Cronin, Lillard was dealt to the rival Milwaukee Bucks, sinking Riley’s team back into play-in territory.

Now, let's fast forward to the aftermath of the trade and re-evaluate a move that shifted the NBA landscape.

Milwaukee Bucks: C

Despite pairing Giannis Antetokounmpo with a future Hall of Fame talent in Lillard, the Bucks had to give up the two-way juggernaut of Jrue Holiday to make it happen. Holiday played a big factor in the Bucks' 2021 championship and had seemingly found a home in Milwaukee.

Instead, the Bucks swapped Holiday for Lillard. Shortly after, the Blazers re-routed Holiday to the Boston Celtics. That helped turn an East rival into the best team in the league. The Celtics went on to win the 2024 title.

How has this panned out for the Bucks? They have gotten worse. They were bounced in the first round of the playoffs last year and are hovering over a handful of games above .500 this season. They went from being legitimate championship contenders to an afterthought in the East.

Portland Trail Blazers: D+

It was clear from day one of Lillard’s trade request that Cronin had zero intentions of dealing with Riley. Whether it was personal between Cronin and Riley or the pressure not to cave to his star player, it became clear that the trade talks with Miami were going nowhere. At the end of the day, Portland refused to respect the wishes of one of the greatest players in franchise history. 

In return, they settled for essentially Deandre Ayton and draft picks. Cronin viewed the Heat’s offer as a lowball, but it may have been a better package than what the Blazers ultimately received. The package would likely have included Tyler Herro, young players and picks.

Herro has blossomed into an All-Star, while Ayton has been a disappointment. The Blazers don't have a clear path out of the bottom of the West.

Miami Heat: F

There were really no winners in the Lillard trade (outside of the Celtics landing Holiday in a subsequent move). But the biggest losers were obviously the Heat. Instead of adding a star and punctuating one of the great eras in franchise history with another chance at a championship, Riley fumbled. 

They were handed the final chance to bring in real help for Butler on a silver platter. If a top-75 player of all time requests Miami and Miami only, there are no excuses not to get the job done.

Not only did Riley’s failure upset the fanbase, but it pushed Butler to the “emo Jimmy” phase, another wasted play-in season and, ultimately, a trade request of his own. And now, the Butler era is over and Miami's title window has slammed shut.

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