Bucks Know Very Well How to Repeat History


Shock is an understatement.

I nearly fell out of my chair when I saw the post from Adrian Wojnarowski.

Just 90 minutes before, I was at lunch explaining to my brother how unrealistic a trade for Damian Lillard would be for the Bucks. 

First, there were the logistics of the trade. How would the Bucks free the proper cap space to take on Lillard’s contract? A pairing of Jrue Holiday and Grayson Allen would work in theory, but it didn’t seem very plausible that Bucks general manager Jon Horst could pull that off. 

Secondly, there was the trade request to Miami. On July 1, Lillard had requested a trade to the very team that eliminated the Bucks in the first round of the playoffs last season. It was Miami or nothing for Lillard. 

According to Chris Haynes of Bleacher Report, the Trail Blazers had refused to engage with the Heat since July. And during that time, Horst was working behind the scenes, chipping away at a deal.

Horst moved in silence to make noise.

Lillard was traded to Milwaukee in a three-team deal involving the Bucks, Trail Blazers and the Suns. Portland landed Deandre Ayton from Phoenix, as well as Toumani Camara, Milwaukee’s 2029 unprotected first-round draft pick and unprotected Milwaukee swap rights in 2028 and 2030, according to Wojnarowski. Portland also landed Holiday, who they reportedly intend to move in another trade.

Phoenix landed Allen from the Bucks, and Jusuf Nurkic, Nassir Little and Keon Johnson from Portland.

The sports news cycle was immediately dominated by the Milwaukee Bucks. You can probably count on one hand the number of times the Bucks have been the subject of a viral moment like this. With the NFL in full swing, it was the Bucks with the spotlight on Wednesday.

Before a series of trades beginning in 2018, the Bucks started with Greg Monroe, John Henson, Matthew Dellavedova and a handful of picks in 2018. Now, they’ve landed one of the greatest shooters in the game’s history. 

Commitment to Giannis, commitment to winning

The consistent commitment to title pursuit from Horst has been stunning. Milwaukee has a generational talent in Antetokounmpo. Many consider him to be the best player in the world, and although he has already helped deliver the franchise its first championship in 50 years, his desire to hang banners has only gotten deeper. 

Horst knows this, and Antetokounmpo’s recent comments to The New York Times earlier this month provided extra motivation to make a big change: “I would not be the best version of myself if I don’t know that everybody’s on the same page, everybody’s going for a championship, everybody’s going to sacrifice time away from their family like I do,” Antetokounmpo said. “And if I don’t feel that, I’m not signing.”

In early September, ESPN’s Brian Windhorst asserted that Antetokounmpo would likely leave Milwaukee at the end of his contract because the Bucks’ championship window is closing and it would become too difficult to retain the superstar in the future. Windhorst believed Antetokounmpo would not sign an extension with the Bucks this fall— and I agree, but not because Antetokounmpo wants out. 

It never made sense for him to sign the extension this fall. According to ESPN, the contract would be worth an estimated $169 million over three years, or just over $56 million a year.

If he waits until next summer, however, he will be eligible to sign a contract estimated to be around four years, $234 million, or nearly $58 million a year.

The comment likely was not Antetokounmpo’s way of saying he wants to move on from Milwaukee. Instead, it may have been intended to put pressure on the Bucks to continue to commit to winning. 

Once again, Horst unabashedly made that commitment. The future picks be damned.

When Antetokounmpo was up for an extension in the fall of 2020 following a disappointing postseason exit to the Heat, Horst shipped out an array of future picks and veteran players, along with Eric Bledsoe, to bring in Holiday. 

Antetokounmpo signed the extension in Dec. 2020, and the Bucks won the championship in July 2021.

Once again, Antetokounmpo is facing a contract decision following an embarrassing exit to the Heat. So, Horst threw caution to the wind and made the trade for Lillard. The Bucks championship window is here and now. You do whatever it takes to hang banners, and the front office continues to show Antetokounmpo they aren’t scared to make bold moves to make that happen.

Parting with Holiday

To make the trade for Lillard, Milwaukee had to part with Holiday and Allen. It couldn’t be Khris Middleton or Brook Lopez because they had just re-signed this summer. So, Holiday had to be involved. 

When you have the opportunity to pair Lillard with Antetokounmpo, you do it. When you have the opportunity to flip Holiday for Lillard, you do it. It’s a no-brainer. 

That doesn’t make it any less bittersweet.

Antetokounmpo echoed that sentiment in an interview with Bleacher Report. According to Haynes, one of the first texts Lillard received was from Antetokounmpo, and it read: “Let’s get this f–ing championship.”

Antetokounmpo spoke on Holiday as well, “Jrue is my f–king brother for life. I love his family. I love him. I appreciate him. I wish him nothing but the best. He blessed me with a f–king championship.”

Holiday was Milwaukee’s championship point guard in 2021. The steal on Devin Booker in Game 5 of The Finals may be the most iconic play in franchise history. Holiday was an all-star, a great teammate, a great man, a great Buck. There certainly should be discussion about a potential jersey retirement for the veteran point guard in the future.

As ecstatic as fans are about landing Lillard, there was somber in the words of many Bucks fans as well.

One fan named Becky on X wrote, “Thank you, Jrue and Lauren Holiday for all the wonderful things you have done for the city of Milwaukee. We will love you forever.”

Losing Holiday and Allen is painful for fans. Both players have had great moments in Bucks uniforms, but when you have the opportunity to get Lillard — you take it.

Of course, now there is the question about where Holiday will be moved. Bucks fans are likely waiting with the teeth clinched as names like the Miami Heat, Boston Celtics and Philadelphia 76ers are floated in potential trade scenarios. The last thing the Bucks faithful want is for one of their Eastern Conference rivals to land Holiday.

Any possible concerns with the trade

There may not be a better duo in the NBA than Antetokounmpo and Lillard. One of the games most dominant finishers of all-time paired with one of the most dominant shooters is a recipe for offensive success.

There are a few concerns, however, which will be addressed before diving into the obvious positives. First, there’s the defensive concern. It’s no secret that Lillard is a considerable downgrade from Holiday defensively. Holiday is one of the best perimeter defenders in basketball, and it won’t be easy to replace his impact. The Bucks will be highly dependent on Antetokounmpo and Lopez’s ability to defend the interior, and a lot of pressure will fall on the shoulders of Middleton to improve his defensive consistency this season on the perimeter.

Milwaukee may lean on MarJon Beauchamp, the young Buck who is entering his second year in the NBA. Beauchamp has the length and size to defend guys like Jayson Tatum or Jimmy Butler. But is he ready for it? In all likelihood, it will be Antetokounmpo himself who has to take on more of those difficult matchups defensively.

Then, there’s the age concern. The trade didn’t make the Bucks any younger, or older for that matter. Both Holiday and Lillard are 33 years old. Allen was actually one of Milwaukee’s youngest core players at 27. 

Lillard’s contract is hefty and it lasts through 2026-27. By the end of it, Lillard will be 37. It’s tough to take that contract on, yes. But it would have been difficult for the Bucks to have upgraded while getting younger at the same time.

Yes, Milwaukee’s age problem still lingers. But, this trade is one that helps the Bucks here and now. As unfortunate as it may sound, the age issue is a future problem that will have to be put on the back burner for now.

Finally, there may be a concern about shifting roles. There’s been a lot of talk of a Batman vs. Robin debate with Antetokounmpo and Middleton in the past. In a recent interview with Middleton on “The Old Man & the Three” podcast in September, JJ Redick said with confidence that Antetokounmpo is Batman. Middleton said never questioned it either, in fact he knew that’s how it needed to be.

Lillard has never been Robin though. Now he is. 

Middleton isn’t really the number two guy anymore either. It’s new territory for these two All-Stars who will now share the backcourt. A luxury of assets is always a nice problem to have, but you have to wonder exactly how it will mesh when the time comes. 

Best duo in the NBA

There should be a lot more excitement in Milwaukee than trepidation. Lillard averaged 32.2 points per game last year. Antetokounmpo averaged 31.1 points. Together they accounted for two of six players in the league that averaged 30+ PPG. 

Antetokounmpo has the most 30+ point games over the last five seasons of any player in the Eastern Conference. Lillard holds that same record in the West. According to Elias Sports, the duo will become the first duo of teammates to have averaged 30+ points the year prior since Elgin Baylor and Jerry West in 1962-63 — those are the only two duos to ever do this.

The pick-and-roll offense between Antetokounmpo and Lillard should prove lethal. Defenses will be forced to hedge out on Lillard, when in the past they may have been inclined to leave Bledsoe or Holiday open in order to stop Antetokounmpo from getting the ball at the rim.

Defensive attention will flock to Lillard and Antetokounmpo, which should only make it easier for Middleton to play at a high level and make big shots. Overall the Bucks offense should see vast improvement, especially with shot creation.

“Roll the ball out with Damian Lillard and four other dudes, that group is gonna score a crap ton of points,” Frank Madden said on an episode of the “Locked On Bucks” podcast on Thursday. “Put him out there with [Antetokounmpo], [Middleton], [Lopez] and anyone who can fog a mirror, and you’re going to score a ton of points.”

Lillard era has begun

Fans are excited, and rightfully so. This is one of the biggest trades in franchise history. 

The Bucks have a habit of making big trades for point guards a year before championships, too. In the spring of 1970, Milwaukee made a huge trade to land NBA legend Oscar Robertson. The Big O teamed up with Kareem Abdul-Jabbar, and the pair led the Bucks to the 1971 NBA Championship. Fifty years later, Milwaukee traded for Holiday and he helped Antetokounmpo lead the Bucks to a title the next year. Now, a third blockbuster trade involving a point guard has gone down in Milwaukee.

Fans are waiting for history to repeat itself.

Damian Lillard Next Stop Bobblehead!

Damian Lillard bobblehead

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About Ben McCormick

Ben McCormick is a sports writer from North Carolina. He has run independent blogs and begun writing for The Lead in 2023. He writes for The Daily Tar Heel as well, where he has worked since September of 2022.

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