The dust settled on the Jrue Holiday deal with the Milwaukee Bucks. The news came out yesterday that the picks Milwaukee will be giving up are all unprotected. There is no restrictor on there in case Milwaukee is bad. This is a significant risk by Jon Horst and the Milwaukee Bucks. This is not to say I wouldn’t have done the Jrue Holiday deal, rather, point out that there is a pathway where this all goes wrong even with Giannis on the team. But is this an overreaction? It very well could be if we use LeBron James and Michael Jordan as our examples.

Here is the pick breakdown on the Jrue Holiday trade:

New Orleans receives

2020 1st (via IND)
2024 right to swap
2025 1st unprotected
2026 right to swap
2027 1st unprotected

— Bobby Marks (@BobbyMarks42) November 17, 2020

Milwaukee is giving up unprotected picks in 2025 and 2027. The assumption is that Giannis Antetokounmpo will be signing his supermax later this week. There is no knowledge about this, but all signs are pointing towards it. .These deals do not happen without knowing Giannis is signing a long-term deal. If he signs a five-year extension, that puts him ready for a new deal in the year 2026. This could make the 2027 unprotected pick a very costly move by the Bucks. Why Milwaukee would not make 2026 unprotected and do the pick swap in 2027 is beyond me.

Giannis is 25 years old. He is one of the best players in basketball. Giannis should be considered with the greats of basketball. If that’s the case, the trajectory of those players from ages 26-31 is pretty good. Both LeBron James and Michael Jordan won titles during that time or found themselves at the tail end of the draft. Jordan took a year off for baseball during that time but the Bulls still were a playoff team that would have drafted in the late 20s. When you have a superstar like Giannis, the assumption is you will never be drafting in the lottery. Bucks are banking that.

The thought of what if there is a Golden State 2020 situation did not cross Horst’s mind. It is something that lurks in the back of your mind as a Bucks fan, but the reality is they should be a successful team for years to come if Giannis stays. Then at 32, maybe he does want to spread his wings, but if the Bucks keep a good core around him, he may go the route of Dirk Nowitzki and Tim Duncan and stay here for life. I do think the Bucks will now work on how to get picks back as the years go on. Brooklyn gave up so much draft capital and before Kyrie and KD came to town, they made a playoff roster without a superstar. My guess is Milwaukee will use that model too.

Who knows if I’m writing, podcasting, or anything else in seven years, but let’s hope I’m not freaking out about this unprotected 2027 pick.

Charlie.