I think this is one of the rare trades that you can say eventually worked out for both sides. For the Bucks, they ended up winning a championship and have a true big three now with the addition of Holiday. There’s obviously the chance that they acquire Holiday while they have Brogdan too, but I don’t think it’s as likely.
Additionally, the first-round pick that they acquired in the deal from the Pacers was flipped to the Nuggets as part of the bigger Holiday trade (it ended up being R.J. Hampton, so not a huge loss at the moment).
For Brogdon, he has been given the chance to be the player he believes he could be. He’s been right on the border of being an All-Star the last two seasons but has been held back due to injuries, another factor as to why the Bucks may not have been as keen to give him that big contract. Regardless, he’s one of the two best players on the Pacers and has developed a nice chemistry with Domantas Sabonis.
The biggest gripe that I have with the deal is how the Bucks front office managed the cap during and after the deal. Getting a big trade exception would have been a huge help in acquiring another rotation player, but they fumbled it.
Again, I would have kept Brogdon. Even if you didn’t believe that he was worth the contract, that’s still a valuable prime-age player who you could include in a future deal, but I also like Brogdon as a player despite the injury issues and think he would have been valuable to the Bucks as well. Nevertheless, it’s moot now and both sides should be happy with their decision.