Winners, Losers and Takeaways of Jrue Holiday Trade to Milwaukee Bucks

Free agency doesn't start until Friday, but the Milwaukee Bucks have already made the biggest splash anyone will likely make this offseason just when they needed to the most.

First, the Bucks agreed to trade George Hill, Eric Bledsoe, three first-round picks and two pick swaps to the New Orleans Pelicans for Jrue Holiday, an upgrade at point guard whom many teams were after. The deal was first reported by Shams Charania of The Athletic and Stadium.

Then, Milwaukee agreed to a sign-and-trade deal with the Sacramento Kings, acquiring sharpshooter Bogdan Bogdanovic for Donte DiVincenzo, Ersan Ilyasova and D.J. Wilson, according to ESPN's Adrian Wojnarowski.

Just days before two-time reigning MVP Giannis Antetokounmpo is eligible to sign the five-year, $220 million extension the Bucks will be able to offer him, general manager Jon Horst has made a strong case to his star for why he should commit long term to the team that drafted him.

Milwaukee gave up a lot for Holiday, but it's a good gamble. Anything that increases their chances of keeping Antetokounmpo is worth doing. Even after finishing with the best record in the east the past two seasons, they haven't been able to reach the Finals, losing to the Toronto Raptors in the Eastern Conference Finals in 2019 and to the Miami Heat in the second round in 2020. Adding Holiday and Bogdanovic gives them their strongest team yet, and their best chance to get over that hump.

But there's plenty more to unpack with these moves, and the Holiday deal in particular.

Holiday upgraded his on-court situation for the coming season, and potentially his bank account well into the future.   

In seven seasons in New Orleans, Holiday played in two postseasons and won one series against Portland in 2018. The new iteration of the Pelicans, with Zion Williamson, Lonzo Ball and Brandon Ingram leading a young core and Stan Van Gundy newly installed as head coach, is exciting and full of potential. But the team has an uphill climb to even make the playoffs in the West.

Milwaukee, on the other hand, is a title contender right now. And with how much the Bucks gave up for him, they'll be highly motivated not to lose Holiday next summer when he can become a free agent. They'll pretty much have to give him whatever he wants, which could mean near-max money.

In a vacuum, that's an overpay. But if trading for Holiday was the final piece to get Antetokounmpo to sign long-term, it's worth paying him on the back end considering where the Bucks would be as a franchise if they lost the two-time reigning MVP.

Antetokounmpo can't yet sign a long-term extension with the Bucks, but after the moves to acquire Holiday and Bogdanovic, all the buzz is trending that way.

If he does indeed re-up, it's a tough break for the teams around the league that have been aligning their cap sheets for a LeBron-in-2010-style run at him. The Toronto Raptors, Miami Heat and Dallas Mavericks have been most strongly rumored to be pursuing Antetokounmpo in free agency, and each would have a compelling case that he should pick them.

All of that may be out the window now.

Fortunately, those three teams are in good positions either way. The Raptors are still contenders in the East, the Heat are coming off a trip to the Finals and the Mavs have maybe the brightest young star in the league in Luka Doncic.

But putting all this energy into planning to lure Antetokounmpo to come up empty isn't fun.

Just as he did when he dealt Anthony Davis to the Lakers last June, Pelicans VP of basketball operations David Griffin got as much back as he could have hoped for in the Holiday deal.

This time, Griffin was dealing from a position of strength. Plenty of teams were interested in Holiday, and the Pelicans would have been perfectly happy going into the season with him still on the roster and trying again at the deadline if Griffin didn't get an offer he liked.

Three future first-rounders for a player who can become a free agent next offseason is a great return, which is to say nothing of Hill and Bledsoe. Both of them can help New Orleans right away as they look to make a return to the playoffs, and if things go sideways, either one can be flipped at the deadline to a contender.

One of them may prove expendable anyway if Ball develops as the Pelicans think he will.

Griffin did well here.

On paper, the Bucks' starting five is killer: Holiday, Bogdanovic, Khris Middleton, Antetokounmpo and Brook Lopez. Don't be surprised if that five-man lineup is the best in the league based on various efficiency metrics.

But as things stand, you can also expect a drop-off from the starters to the bench that rivals the Lob City-era Clippers.

The Bucks had to make these moves to go all-in, but their roster is so top-heavy now that any injury to one of the starters could be devastating. There's a chance Robin Lopez will be back on a new deal after opting out of his contract for next season—a move first reported by Wojnarowski—but beyond that, there isn't much there.

Horst will have to hope he can convince a few veterans to take cheap deals to go ring-chasing to fill out the rest of the bench.

Holiday is the kind of player who makes any team he's on better at both ends of the floor, so there were likely plenty interested in making offers to New Orleans. He would have been great in Denver, Boston or Philadelphia, all of whom were speculated as suitors in recent weeks.

But in the end, no one else was willing to give up the number of draft picks the Bucks were, and that was what Griffin was looking for, so they were the ones who were able to get the deal done. There aren't many upgrades with his level of impact left on the trade market.

Boston has a move to make with Gordon Hayward's contract, which could have been part of salary matching for Holiday. Denver, meanwhile, has a logjam on the wing with Will Barton and Gary Harris both potentially expendable to make room for Michael Porter Jr. to get more minutes.

For the past 18 months, the NBA conversation has been dominated by speculation about where Antetokounmpo will go when he becomes a free agent. It's not hard to see why: player movement drives interest, and fans want to believe their favorite team may be able to sign or trade for a player of his caliber.

But if Antetokounmpo does ultimately decide to stay in Milwaukee, it's good for the NBA. It's a good thing when more franchises are relevant, especially in non-glamour markets. It's a good thing when superstars decide to buck the trend and stay in one place.

Nothing is done yet, but the Bucks have to feel good about what they did on Monday night to convince their franchise cornerstone that it's worth sticking around—and the league is better off for it.