Nobody saw the Milwaukee Bucks acquiring Damian Lillard from the Portland Trail Blazers in a trade just before the 2023-24 NBA season coming.
It was a move shrouded in secrecy, as it was long-rumored that the Miami Heat were eventually going to get Lillard one way or another. Yet, GM Jon Horst snuck into the conversation and got a deal done in a move that even took the players involved by surprise.
Jrue Holiday, who was the outgoing centerpiece of the trade on Milwaukee's end, recently opened up about the entire experience as a guest on The Draymond Green Show.
"I think for me it was just a shock because at least let me know 24 hours in advance. Not five minutes in advance. Maybe I'm asking for too much."
Jrue Holiday's view on Bucks' Damian Lillard trade is understandable but flawed
No one could fault Jrue Holiday for wanting some notice before having to uproot his life and move his entire family elsewhere. On top of that, as Holiday detailed in the episode, it was particularly shocking to him because he won an NBA championship with the Milwaukee Bucks, highlighting just how big of a part of the organization he was for three years.
All of that is reasonable, but when it comes to trades, the Bucks have learned from past debacles, notably the failed Bogdan Bogdanovic sign-and-trade, and keep everything under lock and key these days.
Even with the Patrick Beverley trade this past February, Yahoo Sports' NBA insider Jake Fischer reported that he did not hear Beverley's name surface as a trade target once among dozens of names linked to Milwaukee.
If the Bucks didn't let it slip that they were going after Patrick Beverley, they certainly wouldn't let it be known that they are going after one of the best in the business in Damian Lillard. And that is not to be disrespectful to Beverley, who has been a great addition to this Milwaukee roster. It's just not overly controversial to say that Lillard is more reputable.
With a trade of this magnitude, letting anything slip could have derailed the entire thing. A nightmare scenario where Horst lets Holiday know that he will be involved in a Lillard deal before it is complete, only to have the deal fall through for whatever reason could have happened. If it did, that could have soured the relationship between Holiday and management, causing significant problems.
This thing had to be kept quiet until it was agreed upon. The NBA is a difficult business sometimes, and this was one of the best examples in recent memory. Holiday is justified in his thinking, but the organization's way of handling it also has validity.
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