The trade that sent Damian Lillard to the Milwaukee Bucks for point guard Jrue Holiday and Phoenix Suns center Deandre Ayton was praised roundly be analyst on all sides of the deal. The Portland Trail Blazers elegantly exited what had been a slow, and sometimes acrimonious, slog through negotiations prompted by Lillard’s trade request at the start of free agency in July.
Writing for ESPN Insider [subscription required], Adrian Wojnarowski detailed the months and moments leading up to the Big Trade, including the usual advantages and cautions for all sides. Setting Wojnarowski’s description apart, however, was an emphasis on the secrecy surrounding the dialogue between teams, to the point that one of the parties involved didn’t know what they were being offered until the literal last second.
Wojnarowski started by conveying urgent insistence from Bucks General Manager Jon Horst that the Blazers General Manager Joe Cronin not reveal to anybody the existence of their discussions, let alone potential terms of a deal:
One of the most delicate parts of these superstar trade sagas resides in teams’ needs to protect players under discussion, sparing feelings and preventing punctured locker rooms by keeping starry names out of the public news cycle. Cronin had to contend with a player agent who wanted to squash any deal that didn’t include Lillard landing with the Miami Heat, and Horst wanted to protect the sanctity of his championship core...
...From the earliest days of July, Horst told Cronin that their periodic conversations on Lillard had to stay secret — or the Bucks would bail. Horst didn’t want Holiday to become leverage for the Blazers in trade talks on Lillard elsewhere, which precluded Portland’s ability to shop the possibility of Holiday’s availability to those teams where he fit...
...That’s why Horst told Cronin that the only way a deal could happen would come with Portland canvassing the league and ultimately circling back to negotiate one-on-one with Milwaukee. That started on Sunday night. The Bucks’ assets to make a trade work were easily discernible — the 2029 first-round pick, 2028 and 2030 pick swaps and, yes, the two-time All-Star guard, [Jrue] Holiday.
Wojnarowski claims that Horst kept his own roster in the dark, particularly former league MVP Giannis Antetokounmpo, whom he did not want to burden with the decision.
The silence kept considerable pressure on Cronin, who appeared to be doing little in the way of negotiation, despite the urgency of Lillard and his agent, Aaron Goodwin.
Cronin’s peers, who had been in these circumstances, privately told him what he had publicly declared: His obligation was to find the best deal for the Blazers, not for Lillard. If those conflicting elements matched up, even better for everyone.
Through it all, Cronin told himself: Eliminate the emotion, the frustration, the fatigue. And most of all, Cronin implored himself: Don’t settle. Don’t let yourself settle.
The deal ended up involving a third team, the Phoenix Suns, who sent Ayton to Portland in exchange for Blazers center Jusuf Nurkic, forward Nassir Little, guard Keon Johnson, and wing Grayson Allen from the Bucks. Per Wojnarowski, Cronin could not tell his counterparts in Phoenix who the final player would be, leaving them in the dark until the final phone call:
To this end, the Suns could never know the third team in the trade. Cronin kept Suns CEO Josh Bartelstein on the line for months and weeks and days, and finally, hours on Tuesday and Wednesday. Bartelstein, general manager James Jones and owner Mat Ishbia could go days without hearing from Portland, but Cronin would always circle back and keep them abreast.When Cronin and Horst went to sleep on Tuesday night, they were confident that they had a trade to complete on Wednesday. The Blazers and Bucks just needed to close out terms with the Suns, and they had a deal.
Here’s what made that delicate, though: If the deal fell apart, Horst didn’t want another team to know how far along these Blazers-Bucks talks had gotten. The Suns knew they were getting Portland’s Nurkic, Nassir Little and Keon Johnson in a three-team trade, but the Suns had to get one more asset to make this deal workable. In almost all cases, Cronin would’ve told Bartelstein that he was getting Milwaukee guard Grayson Allen, but Horst’s insistences on secrecy made this different.
Cronin did tell Bartelstein the general salary and position of the mystery player, so the Suns were able to deduce down to two players who that might be — Allen and Oklahoma City’s Victor Oladipo, who is recovering from a serious leg injury. The Thunder are sometimes on the periphery of these big deals, so the Suns thought that was a possibility. Of course, the Thunder were nowhere near this trade.
Cronin kept telling Bartelstein: Just trust me. You’re going to like the mystery player. Trust me.
Wojnarowski also describes the enthusiasm in the Suns’ front office at receiving Allen, plus many more details about Cronin and his management style.