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The Jrue Holiday trade proves the Bucks are going for it all this season

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This is it folks.

Milwaukee Bucks v Miami Heat - Game Four Photo by Garrett Ellwood/NBAE via Getty Images

All in.

Whether that phrase conjures up Luke pledging his love to Lorelai in Gilmore Girls or Daniel Craig pushing all his chips in during Casino Royale, for Milwaukee Bucks fans, it will forever be tied to the twilight hours of November 16, 2020. As that magical night turned to early morning, Adrian Wojnarowski and Shams Charania broke the news that Jon Horst wasn’t content with fringe moves. Instead, he’d be jettisoning any semblance of a youthful future, giving up Eric Bledsoe, George Hill, three first round selections and two pick swaps for Jrue Holiday. Then, around an hour later, Kevin O’Connor first mentioned that the Bucks were pursuing the long-rumored Bogdan Bogdanovic sign and trade. Woj confirmed later it would be Ersan, D.J. Wilson and Donte DiVincenzo heading to Sacramento in the deal.

And just like that, in the span of an hour, your Milwaukee Bucks became an entirely new squad. For anyone fearing a stale, rerun of a regular season next year, there’s a whole new cast to liven things up.

The Bucks have never made an all-in trade of this magnitude before. They’ve been on the other side of it, when the Lakers gave up a boatload of prospects back in the day for Kareem Abdul-Jabaar. Horst sacrificed every ounce of draft capital he could for Jrue Holiday, a player they believe will be the perfect stylistic and cultural fit in Milwaukee. In Bogdanovic, they get the do-it-all wing who can slot next to Jrue and Khris, can moonlight in both backcourt spots and hopefully translate into the postseason, an experience he never had in Sacramento.

Let’s call a spade a spade, the cost was massive. Effectively five first round picks is, in a vacuum, an overpay for Jrue Holiday. He’s never been an All-Star (probably somewhat a Western Conference problem), and isn’t touching the star potential of players like Chris Paul, James Harden, Paul George and other recent malcontents on the move. One thing he isn’t though: a malcontent.

One of the clear signals of this move, and the lack of noise around Chris Paul, is that Horst, Giannis, Bud, and the Bucks organization values their “no assholes” ecosystem to the umpteenth degree. Holiday isn’t a pure injection of talent, he’s a combination of fit, talent and character. He’s the kind of player Giannis probably would want to spend his prime playing with, rather than some easily alienated superstar whose feet freeze up the second he touches down in the General Mitchell airport.

The only question that mattered this next season was whether Giannis Antetokounmpo would sign a supermax and commit to the Bucks franchise for another five years. The quickest path between Jon Horst’s office and Giannis signing on the dotted line was an NBA championship, or a roster better equipped to win an NBA championship. A first round selection in this year’s draft wasn’t going to accomplish that. Neither was a fringe move for a competent PG who clears the lowest of bars that Eric Bledsoe set. Given the Bucks’ realistically difficult path to a blockbuster trade like this, that only further signals the fact that Horst wanted to do whatever possible to shore up his chances that Giannis would commit to the Bucks. If I were him, considering my best postseason players, and saw this:

2019-20: Giannis, Khris Middleton, Brook Lopez.............George Hill?.....Eric Bledsoe (MAYBE but secretly Wes Matthews or Donte Divincenzo?)

And thought that I could turn it into this:

2020-2021: Giannis, Khris Middleton, Jrue Holiday, Bogdan Bogdanovic, Brook Lopez

Ya, I’m doing that. Now, there are many, many potential downsides here. Giving up a BOATLOAD of picks is terrifying, but I can’t imagine it reaching Brooklyn-Boston levels of misery even in the darkest of timelines. Jon Horst seems to take sick pleasure in putting together the most [Zach Galifanakis number gif] pick protections on his transactions. I’d be incredulous if he didn’t do the same here should the bottom fall out of this roster and Giannis leaves. Jrue is only locked in to one more season before he has a player option for 2021-22. One imagines the Bucks would’ve already arranged some sort of wink-wink deal with him given the level of capital they committed, but that’s never assured. Still, this goes back to the character fit. I think of Jrue Holiday as a considerably more good-faith actor than most of the empowered superstars who have been on the move in recent years.

Bogdan Bogdanovic seems like an ideal fit as a fourth banana in Milwaukee, but that sign-and-trade will hard cap Milwaukee, making it difficult to maneuver filling out their roster. Maybe they whiff and have an entire benchful of flotsam. But, if last year showed anything, it’s that clearly some players are willing to sacrifice salary and come to Milwaukee, frigid temps and all. The Bucks weren’t looking like they were in as strong of a position to lure players after their flameout last season. By making these moves in advance of Friday, Horst has positioned them with considerably better leverage to lure the ring chasers. Still, it’s on him to execute, particularly after potentially losing both Wes Matthews and Robin Lopez following their opt outs.

Like it or not, these two moves are the culmination of a lot of mismanagement during Giannis’ time in Milwaukee. They’ve squandered first round picks (Thon Maker, Rashad Vaughn, D.J. Wilson, Jabari Parker), signed players to contracts they had to package assets to offload (John Henson, Matthew Dellavedova, Miles Plumlee), allowed assets like Malcolm Brogdon to leave without maximizing them to the full extent (I know the trade exception is a little thing, but the little things are what win championships) and their owners have skirted the luxury tax time and again despite their reported willingness to pay it.

But my palms are raw, and I’m sure yours are too, so I’m giving you permission to quit hand wringing over the past. Jon Horst just built a roster that is constructed to win immediately. If Jrue and Giannis re-signs, your core of Giannis, Jrue, Khris, Brook and Bogdan are here for at least these next three seasons. That is your window. There’s no future left to consider, because there are basically no assets for Milwaukee’s future right now. The Bucks are all in, and every fan can be too, because if they win it all, those five guys will be the core of a Bucks championship team. And if they lose; if it all falls apart; if Bud can’t figure it all out; if Jrue gets injured or Giannis leaves...

We’ve been there before, it’s just back to business as usual for us Bucks fans. 8th seed or bust.