As “Dame Time” expires in Portland, the championship clock resets in Milwaukee

The storyline of the NBA off-season was Damian Lillard’s trade request and the eventual block buster move to follow.

Three months later, Lillard remained a Trailblazer as trade talks with the Miami Heat stalled and fan interest disintegrated with each passing day.

As the NBA offseason calendar shifted to September and there was no trade in sight to his preferred trade destination of the Miami Heat, Damian Lillard incorporated himself back into the Portland Trail Blazers’ ecosystem. For the last two weeks, team sources say Lillard has been working out at the Blazers practice facility, interacting with players and coaches.

Would they reconcile and finish out the loyalty storyline? No, but Dame was willing to play a good soldier until a trade was agreed upon.

On a call between Lillard’s agent, Aaron Goodwin, and Blazers general manager Joe Cronin earlier this month, it was communicated that Lillard would be content rejoining Portland for training camp. Lillard let the Blazers know he was willing to be fully present for the start of the 2023-24 season, if only to give the organization more time to work toward a potential trade with the Heat, sources briefed on those conversations say. But according to league sources, Cronin expressed skepticism about that approach. The Blazers were determined to get a deal done before the start of camp.

Cronin and his front office have amassed tremendous young talent in Scoot Henderson and Shaedon Sharpe, and the Blazers were ready for a drama-free camp.

So the Blazers made the much-awaited blockbuster trade on Wednesday, trading Lillard to the Milwaukee Bucks in a three-team deal that sent Jrue Holiday, Deandre Ayton, Toumani Camara, a 2029 first-round Bucks pick and two Bucks pick swaps in 2028 and 2030 to Portland. Jusuf Nurkić, Nassir Little, Keon Johnson and Grayson Allen are off to Phoenix.

The trade has massive implications for the landscape of the NBA. The Bucks are now one of the favorites to win the 2024 championship, teaming Lillard with Giannis Antetokounmpo, Khris Middleton, Brook Lopez, NBA Sixth Man of the Year candidate Bobby Portis and shooters Pat Connaughton and Malik Beasley.

After he made public comments about being unsure about the Bucks’ desires to contend for a title and being unsure himself of signing an extension, Antetokounmpo has been delivered an All-NBA player who is a perennial All-Star and was voted onto the NBA’s 75th-anniversary team.

In 2020, with Antetokounmpo’s future uncertain ahead of what was a super-maximum contract extension, the Bucks traded for Holiday to push the team closer to a championship. Eight months later, they secured their first NBA championship in 50 seasons with a victory over the Suns in the 2021 NBA Finals.

Three years later and with similar questions about Antetokounmpo’s future amid extension eligibility, Bucks general manager Jon Horst lands Lillard by making the tough and emotional decision to trade Holiday, the player for whom he traded to help the Bucks secure that title in 2021. And the move could go a long way in securing the future of the Greek Freak once again.

But this was a deal that shocked much of the NBA world. With much of the expectation throughout this process being that Lillard could end up in Miami and with the loudest chatter in the days before the blockbuster trade being that he could go to Toronto, a deal with the Bucks seemed to be far off the radar.

Here’s how it all came together.

From the moment Lillard requested a trade from the Blazers on July 1, he informed the team that he wanted a deal specifically to the Eastern Conference champion Heat, sources briefed on those talks say. Lillard believed he gave the Blazers loyalty over 11 seasons and wanted the franchise to move him to his preferred landing spot.

The Blazers and Heat had multiple conversations in July, but the sides never engaged in substantive negotiations, according to those sources. For their part, the Heat, league sources say, were prepared in July and August to offer up to three first-round draft picks — with Tyler Herro going to a third team — and multiple second-rounders and swaps along with expiring contracts and 2022 first-round pick Nikola Jović. But the Blazers were disinterested with each side developing a level of contentiousness.

As the Blazers began to start serious trade talks across the league on Sept. 18, a bevy of teams — the Bucks, Boston Celtics, New Orleans Pelicans, Toronto Raptors, Minnesota Timberwolves and Chicago Bulls — all showed interest in Lillard.

Once Lillard was convinced that joining the Heat was virtually impossible, sources briefed on discussions say he became open to the prospect of playing for the Bucks and the Brooklyn Nets. This allowed the Blazers and Suns to pick up on their idea of swapping Ayton and Nurkic, in a 3 team deal that sent Dame elsewhere. So the backchannel talks quickly picked up.

The Blazers began discussing the framework of the Suns’ involvement with the Ayton-for-Nurkić swap in mid-July but needed two months to find the third team for Lillard and ensure that they wouldn’t be entering the luxury tax given Ayton is on a max salary. The Suns didn’t care if it was the Heat Bucks or Nets, they wanted this deal done, so do not sleep on their fingerprint on this deal getting done.

For the Trail Blazers, Phoenix was an essential component of any Lillard trade. Portland valued Ayton, 25, as a foundational piece to anchor a roster headed by Henderson and Sharpe, and the talented big man is sure to be a 20-and-10 threat in his new home. In terms of Holiday, the expectation around the league is that the Blazers will work on finding the two-time All-Star a new home with several playoff contenders squarely in the mix.

In Phoenix, Nurkić is seen as a better fit for the Suns’ style of play and culture, and his contract (three years, $54.4 million), compared to Ayton’s deal (three years, $102.1 million) gives the franchise additional flexibility moving forward on a roster with three max salaries in Devin Booker, Kevin Durant and Bradley Beal.

Milwaukee became seriously engaged over the last week, believing that pairing Lillard with Antetokounmpo would serve as a convincing factor for Lillard to want to be with the Bucks, even though they weren’t his original preferred destination.

Now, Antetokounmpo is eligible for a three-year, $186.6 million extension with the Bucks before the start of the regular season or a commitment for up to four years and $260 million next offseason. The Bucks delivered the max, three-year extension to Antetokounmpo in recent days, league sources say, and it is immediately unclear how he and his representatives will reconsider a potential deal now versus waiting to evaluate after the season.

For Lillard’s part, he finally gets the chance to win it all, something he has always wanted, even if the city where he landed isn’t exactly what he had in mind.

He has everything but a championship on his résumé. Seven All-Star appearances. Seven All-NBA selections. All those playoff memories that helped make him the greatest Blazers player of them all.

But this — a title-contending roster that fits so well with his generational skill set — is what he always dreamed of in the City of Roses.

“In a perfect world, I could spend my entire career in Portland,” he said on a podcast earlier this month.

This was an imperfect process, to say the least, and a flawed pairing in these recent years. But both sides found a way to win, just in time for the games to begin.

So with Dame narrowing his sights on the Larry O’Brien trophy, the Blazers have their sights set on the future of RIP CITY.

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