Trade discussions between Jon Horst and Joe Cronin involving Damian Lillard began in early July, reported Adrian Wojnarowski of ESPN.

Horst was adamant about keeping the discussions a secret as he didn't want the Blazers to use Jrue Holiday as leverage in other negotiations.

The Blazers, who were looking to acquire Deandre Ayton even before trading Lillard, kept the Suns and team CEO Josh Bartelstein in the dark about their negotiations with the Bucks.

Cronin told Bartelstein the general salary and position of the player the Suns would be acquiring in a potential three-team deal involving Ayton and Jusuf Nurkic. 

The Suns, who were looking for one more piece alongside Nassir Little, Keon Johnson, and Nurkic, deduced they would be receiving either Grayson Allen or Victor Oladipo before Cronin confirmed that the Bucks were the third mystery team.

The situation between Damian Lillard's camp and the Portland Trail Blazers became so contentious during the month of September that the NBA league office intervened. 

A Zoom meeting was organized by the NBA on Sept. 23rd with league officials, Joe Cronin, Damian Lillard, Aaron Goodwin and NBPA general counsel Ron Klempner attending.

The meeting was scheduled with the purpose of opening up the lines of communication between the Blazers and Lillard's camp.

Both sides expressed their trust issues with the other during the meeting.

Cronin promised to do a better job communicating and started to do so again with Goodwin.

During a September 5th meeting when the Portland Trail Blazers made it clear a trade with the Miami Heat was unlikely, Damian Lillard asked to rescind his trade request to remain with the franchise.

Joe Cronin responded by saying to Lillard that there was no coming back.

Sources tell Chris Haynes of Bleacher Report that "Lillard was shocked."

Lillard began showing up to work out at the Blazers' practice facility on Sept. 11th and went in for eight days. Lillard said Cronin did not address him once.

"I went into the facility because I was still on the roster and usually that time of the year is when team activities start to pick up as a group. I wasn't confident I would be moved so I showed up to be in the mix," Lillard told Bleacher Report.

Lillard met with Aaron Goodwin on Sept. 17 to discuss a contingency plan with the Milwaukee Bucks and Brooklyn Nets the preferred alternative teams. 

The Milwaukee Bucks did not approach Giannis Antetokounmpo before they moved forward with their trade of Jrue Holiday for Damian Lillard.

"Directly, he literally played no role," said Adrian Wojnarowski. "In fact, Jon Horst did not bring this trade idea or sign off on it to Giannis Antetokounmpo because Jrue Holiday was involved. And the relationship there and the reverence that this organization and these players have for Holiday. He did not want to put that to Giannis Antetokounmpo and have him have that on his conscious necessarily that he might sign off or not sign off on it."

The Bucks believe their trade for Lillard improves their title odds, while also increasing the likelihood Antetokounmpo chooses to eventually sign an extension.

Milwaukee also didn't approach Antetokounmpo on whether he would commit long-term if they traded for Lillard.

The Milwaukee Bucks are interested in signing Cameron Payne, sources tell Jake Fischer of Yahoo Sports.

Payne was waived by the San Antonio Spurs this offseason following his trade from the Phoenix Suns.

The Bucks lack depth at point guard behind the newly acquired Damian Lillard. 

Damian Lillard communicated to the Portland Trail Blazers that he was willing to be patient and let the season play out if it meant he could eventually be traded to the Miami Heat.

Lillard has been working out at the Blazers' practice facility over the past two weeks, interacting with players and coaches.

Joe Cronin expressed skepticism about Lillard beginning training camp with the Blazers and it became clear they would try to resolve the trade situation before media day on Oct. 2.

Lillard believed his loyalty to the Blazers since he was drafted in 2012 meant they would accommodate him with his trade request to the Heat. Lillard wanted the Blazers to try to find a workable deal with the Heat and that wish went unfulfilled. 

Lillard's camp had a realization that he would need to begin to seriously consider the possibility of playing somewhere other than Miami.

Cronin stopped responding to all communication from Lillard's agent, Aaron Goodwin, in mid-September as tension increased between both sides.

Once Lillard was convinced a trade to the Heat was virtually impossible, sources say he came open to the prospect of playing for the Brooklyn Nets and Milwaukee Bucks. The Toronto Raptors had serious interest in trading for Lillard, but his resistance to playing for that franchise remained an obstacle. 

When the Portland Trail Blazers first spoke with the Miami Heat on a potential Damian Lillard trade, they asked for either Jimmy Butler or Bam Adebayo back in return.

The Blazers and Heat had multiple conversations in July, but sources say the two sides never engaged in substantive negotiations. The Heat believed the Blazers had little interest in engaging on a trade with them.

Sources say the Heat were prepared in July and August to offer up to three first round picks with Tyler Herro going to a third team plus multiple second rounders, expiring contracts and Nikola Jovic.

Lillard wanted the Blazers to try to find a deal with the Heat, but those wishes went unfulfilled in his mind.

The Blazers eventually traded Lillard to the Milwaukee Bucks with Jrue Holiday as the centerpiece return, which they will now attempt to trade elsewhere. 

While Damian Lillard requested a trade to the Miami Heat and attempted to direct himself there, he has accepted the deal the Portland Trail Blazers ultimately made with the Milwaukee Bucks.

Agent Aaron Goodwin attempted to get Lillard to the Heat with both public and private comments. Goodwin spoke with Anthony Chiang of the Miami Herald about Miami's efforts to trade for Lillard shortly after the deal with the Bucks was reported.

“They did everything they could to acquire Dame," said Goodwin. "It takes two to get a deal done. I appreciate all that Pat [Riley], Andy [Elisburg] and Micky [Arison] did to try and make this happen.”

The Heat and Blazers never made much progress in their trade talks. Miami offered a package built around Tyler Herro and at least two first round picks.

In an interview published the day before the Milwaukee Bucks traded Jrue Holiday for Damian Lillard, he revealed how much he wanted to remain with the franchise he was traded to in 2020. Lillard also cleared up his comments from May 2022 that he was contemplating retirement when his current contract expires in 2025.

“No, I don’t plan on retiring. I don’t plan on retiring,” Holiday told the Journal Sentinel, leaning back on an orange leather couch set back off the balcony of SRGN Studios in Los Angeles.

“Just them being my friends and we’ve talked about stages in basketball and sometimes you go through modes or hard spots where like, even with my family, maybe the best thing to do is retire or even just being tired and being exhausted, playing a lot of basketball. But no.

“My answer is no, I’m not retiring.”

Holiday was asked if is open to signing an extension with the Bucks.

“Would love to,” he said. “Before I even won here I think I said I’m a Buck for life and I mean that like deep in my heart. I don’t want to play for any other team. I think we have a chance to continue to do great things as the Bucks team and organization so I want to be in Milwaukee.”

Since the Bucks agreed to trade Holiday to the Blazers, there is reported interest from the Philadelphia 76ers and Miami Heat.

The Milwaukee Bucks have been moved by oddsmakers as the team with the best chance to win the 2024 NBA championship at +400 following their trade for Damian Lillard.

The Denver Nuggets rank second at +475, followed by the Boston Celtics at +500 and Phoenix Suns at +650.