Winners and Losers from Milwaukee’s Jrue Holiday, Bogdanovic trades

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If fortune favors the bold, then right now it favors the Milwaukee Bucks.

In a series of moves clearly aimed more at making Giannis Antetokounmpo happy and pushing him to sign the supermax contract they will offer him — and making the Bucks better on the court — Milwaukee acquired Jrue Holiday from the Pelicans in one trade and Bogdan Bogdanovic from the Kings in a separate sign-and-trade deal. Milwaukee gave up a lot — three first-round picks, a couple of pick swaps, and key players like Eric Bledsoe, George Hill, and Donte DiVincenzo to make it happen.

Who are the winners and losers from these trades? Let’s break it down.

Winner: The Milwaukee Bucks (if Antetokounmpo signs extension)

Five first-round picks — the No. 24 pick in this year’s draft, plus two future first rounders and two pick-swaps — is a steep price to pay for Jrue Holiday, a guard who has not made an All-Star team since 2013 and can opt-out after the season and become a free agent. That’s how many picks the Lakers gave up to get Anthony Davis. Plus, the Bucks gave up a young player they like in Donte Divincenzo as part of the Bogdan Bogdanovic trade with Sacramento.

And it is worth every last bit if Giannis Antetokounmpo signs the supermax contract extension the Bucks will put in front of him of at least $228.2 million (it could be more depending upon where next year’s salary cap falls).

That is the end game of all these moves, to keep the two-time MVP that is Mr. Everything for the franchise. Holiday and Bogdanovic should be an upgraded starting backcourt, providing plenty of shooting, plus Holiday brings improved defense and switchability on the court. Right now the Bucks starting five of Holiday, Boganovic, Khris Middleton, Antetokounmpo, and Brook Lopez may be the best in the NBA. Put decent depth around that and the Bucks will be clear contenders. Antetokounmpo couldn’t have asked the team to be bolder in building the right contender around him.

But will he sign the extension now or keep his leverage open…

Loser: The Milwaukee Bucks (if Antetokounmpo ultimately doesn’t sign extension)

Antetokounmpo has been playing a leverage game — the threat of him leaving has the two-time MVP sitting down with ownership to talk about the future of the team, then making these trades to revamp the backcourt. Antetokounmpo’s game has worked.

So why give up that leverage and sign the supermax extension before this season starts? Antetokounmpo can sign that exact same deal for the exact same money next offseason and keep his power over the organization.

That power is the threat of him leaving. Dallas, Miami, and Golden State are all poised if Antetokounmpo wants to jump to another contender, and every other team would move whatever it took if he wanted to come there. If Antetokounmpo does decide to leave, the Bucks will have just given up any chance of a quick rebuild with all those picks sent away. If Antetokounmpo leaves after this, the Bucks are screwed.

Winner: David Griffin and the Pelicans front office

New Orleans would like to make the playoffs this year. They have Zion Williamson and Brandon Ingram, plus a new coach in Stan Van Gundy that should improve the team’s defense.

However, the Holiday trade signals the Pelicans are not thinking “go all in this year” but rather “let’s build something that will contend in the West in a few years, and for a long time.” That is the smarter play. Between the Holiday and Anthony Davis trades the Pelicans added Ingram, Lonzo Ball, Josh Hart plus SIX first-round picks and four pick-swaps. Those picks are likely later in the first round (Bucks and Lakers) but it’s a steady supply of young talent and/or trade assets that allows them to build a true contender around their young core. The Pelicans are making the right, patient play in building a team.

Loser: Denver, Boston, L.A. Clippers, Portland, other Jrue Holiday suitors

There was an incredible amount of interest in trading for Holiday, and all those teams have now missed out. Denver was considered a frontrunner around the league and Holiday is a player who could have pushed the Nuggets up with the Lakers in the West. The Clippers are still looking for a shot creator and floor general who can defend, a perfect description of Holiday. Boston reportedly kicked around a trade moving Gordon Hayward for Holiday. And the list goes on and on.

None of those teams would have potentially overpaid in picks to land Holiday the way the Bucks did (none had the incentive of keeping Antetokounmpo like the Bucks did), so maybe they don’t see it as missing out. But all of those teams could have used Holiday and aren’t going to find answers near as good in a thin free agent point guard market.

Winner: Buddy Hield (in the Bogdanovic trade)

Last season, Luke Walton started Bogdanovic in front of Buddy Hield, who had just signed a four-year, $94 million contract extension. Suddenly Hield was unhappy and trade rumors for him were popping up.

This move puts Hield back in the starting lineup next to De'Aaron Fox, and it shows new Kings GM Monte McNair has Hield’s back. That should make the petulant star happy for a while. Sacramento also picks up a quality guard off the bench in Donte DiVincenzo, who is still on his rookie contract ($7.7 million total over the next two seasons, a lot more affordable than Bogdanovic for the Kings).