The Bucks were interested in acquiring Damian Lillard immediately after he made his trade request on July 1, but the deal didn’t start to come together until this past Sunday.
As Adrian Wojnarowski writes in an in-depth story for ESPN (Insider link), Bucks GM Jon Horst told Trail Blazers GM Joe Cronin from the outset that their talks had to remain a secret or Milwaukee would withdraw from negotiations.
According to Wojnarowski, Horst didn’t want Jrue Holiday to be involved in any trade rumors, or used as leverage by Cronin with other teams to increase offers for Lillard. The Bucks didn’t want to disrupt their chemistry and hold Holiday in very high regard. That meant Cronin was unable to gauge Holiday’s market value before agreeing to the trade.
As Wojnarowski details, Horst told Cronin that the only way a deal would work is if the Blazers took their time fielding offers and eventually circled back to Milwaukee for one-on-one talks. That started Sunday evening, with both sides feeling like they had reached a breakthrough.
Cronin was determined to say patient and accept the best possible offer, per Woj, and kept details of Lillard negotiations hidden from prying eyes. Lillard’s agent, Aaron Goodwin, was determined to steer him to Miami, but Lillard didn’t have much leverage. Wojnarowski strongly suggests Cronin felt the need to keep things private from Goodwin in case he tried to tank trade talks with non-Heat teams.
One of the most fascinating and “delicate” parts of the deal was Phoenix’s involvement. According to Wojnarowski, the Blazers and Suns had the outline of a trade together for months — Deandre Ayton to Portland for Jusuf Nurkic. Cronin wanted to tie that agreement into any Lillard trade, so throughout the offseason he kept circling back to the Suns.
However, as Wojnarowski writes, due to Milwaukee’s insistence on secrecy, Cronin was unable to tell Suns CEO Josh Bartelstein the final details until the last minute. According to Woj, Phoenix knew it was getting Nurkic, Nassir Little and Keon Johnson from the Blazers in a three-team deal, but the Suns wanted another asset in return.
Cronin was unable to tell the Suns who that player was — or who he played for. Cronin did tell the Suns the mystery player’s position and gave an approximation of his salary, and Phoenix was able to deduce it was either Thunder guard Victor Oladipo or Bucks guard Grayson Allen.
Only on Wednesday afternoon — just before the trade was made public — did Cronin confirm that it was Allen, whom the Suns had reportedly been interested in for several months. According to Wojnarowski, Bartelstein, GM James Jones and owner Mat Ishbia quickly discussed and then agreed to the deal.
The Blazers were happy and relieved to have completed the deal, per Woj, and believed they did right by Lillard by sending him to a contender, even if it wasn’t his preferred destination. Shortly thereafter, Cronin was bombarded by calls inquiring about Holiday, who is now the hottest name on the trade block.
Wojnarowki’s full story is definitely worth reading in full if you subscribe to ESPN+.