Bucks-Celtics Rivalry Set to Reach Its Peak in 2023-24


“You can’t get something without giving up something in this league,” Bucks general manager Jon Horst said.

When the Milwaukee Bucks traded Jrue Holiday to acquire Damian Lillard from the Trail Blazers, the Celtics were likely on Horst’s mind. After an early and brutal exit in the first round of the playoffs last season, Milwaukee was in need of a change. After all, the other Eastern Conference contenders — like Boston — were already making moves.

The Celtics acquired Kristaps Porzingis from Washington in late June. That addition was certainly an offensive upgrade in the interior for Boston, but it came at a price. They had to give up 2022 NBA Defensive Player of the Year, Marcus Smart

Smart was the heart and soul of a talented and often physical Celtics defense. With its floor general gone after nine years with the franchise, Boston was in need of a point guard and a perimeter defender.

On Oct. 1, they got their man. And it was a nightmare scenario for Horst and the Bucks.

Holiday was sent to the Celtics in a deal that sent Robert Williams, Malcolm Brogdon and two future first-round picks to Portland. He was the missing piece Boston needed. 

Milwaukee’s primary rival in the East, an ‘Adversary in April’ since 2018 for the Bucks, had swooped in and acquired their former championship point guard. Not only was Milwaukee parted from Holiday, they will have to go directly through him to get back to the Finals.

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Boston got their guy

Celtics fans are rightfully excited to see Holiday, the 2023 NBA All-Star, paired with Porzingis, Jayson Tatum and Jaylen Brown. The offensive potential of those four players is undeniable, even if Holiday sometimes struggles.

All four players averaged 19 points per game or higher last season and will prove tough to defend for any team in the league. Holiday’s impact will mostly be felt on defense, though. For years, opposing players have heralded Holiday as one of the league’s premiere perimeter defenders.

But his defensive abilities stretch further than the perimeter. He is capable of guarding one through five. 

He is physical and strong, which makes him tough to handle for opposing guards, and allows him to defend larger forwards like Jimmy Butler. Although Butler certainly got the better of Holiday in last year’s playoffs. 

The Celtics already had a strong defensive unit, but adding Holiday will ensure they will be able to hang tough with a usually-stellar Milwaukee defense (which undoubtedly took a hit after losing Holiday).

Thinned out the post

Boston lost Grant Williams to Dallas this offseason, and as aforementioned they traded Robert Williams to Portland. That means their frontcourt has been severely thinned out. That could spell trouble for the Celtics.

Damian Lillard or no Damian Lillard, priority one for any team playing the Bucks is to attempt to contain Giannis Antetokounmpo. Many believe Boston has done a good job of containing him in the past by implementing the strategy often referred to as “building a wall” in the paint. Tough frontcourt players like Grant and Robert Williams, along with Al Horford made life difficult for Antetokounmpo.

Some may argue the Celtics have not actually been successful against Antetokounmpo in the playoffs given his numbers in the 2022 series between the two teams. Giannis averaged 33.9 points, 14.7 rebounds and 7.1 assists through seven games in that series. Clearly, if there was struggle, it was often overcome.

But there is some truth to the Celtics’ defensive success against the Greek Freak hidden in the numbers.

During that series, Antetokounmpo shot 45.6 percent from the floor. The year prior, he shot 56.9 percent from the field during Milwaukee’s championship run. An 11 percent dip is significant. So, Boston’s frontcourt was forcing tough shots, and that’s the ultimate goal against Antetokounmpo. You can’t really stop him, but you can slow him down.

There are serious concerns about whether this new Boston frontcourt can do that. Horford is still there, but at 37 years old, he isn’t getting any younger. Porzingis on the other hand is much taller than Boston’s previous frontcourt players.

But he’s not exactly a defensive upgrade. 

Still, Porzingis is underrated as a shot blocker. His size and leaping ability make him a legitimate threat as a rim protector. Whether he can protect the rim from Giannis in the playoffs, well that’s yet to be seen.

Who was the better addition? Dame or Jrue?

To some, this may seem like a silly question, but given Holiday’s ability as a defender, it’s a question that deserves at least a little thought.

From an offensive standpoint, there’s no doubt the Bucks not only upgraded, but found a perfect pairing with Lillard and Antetokounmpo. 

Lillard’s threat as a three-point shooter in the pick-and-roll with Giannis will be incredibly tough to defend. Milwaukee has added a player that is a nightly threat to score 30, 40, 50 — even 70 points. That really says all you need to know.

Here’s another way to look at it. In the five postseason games for Milwaukee last season, Holiday shot 28.6 percent from three on 8.4 attempts per game. As a top offensive option, Holiday struggled — especially as a three-point shooter. Lillard is not likely to struggle in the same way.

The Bucks paired arguably the modern game’s greatest rim threat with one of the greatest shooters of all-time. Adding floor spacing around Giannis is crucial, so the addition of Lillard (and Malik Beasley) should work well.

On the other hand, Milwaukee’s perimeter defense took a hit — a massive hit. In 2022-23, Lillard had a defensive rating of 120.8, which isn’t great. There are a lot of question marks surrounding who will be the elite wing/perimeter defender for the Bucks with Holiday gone.

Lillard and Beasley are not elite defenders. Khris Middleton has battled so many injuries throughout the last few seasons, that it’s reasonable to wonder whether he can physically take on the most difficult defensive assignments in May. Pat Connaughton isn’t a horrible option, but I’m sure Bucks fans would rather not see him defending Tatum. That leaves Jae Crowder and MarJon Beauchamp, who are probably the two best options in the playoffs.

We know Crowder is capable of defending at a high level, but there are still a couple of questions. One, can he still defend players like Tatum and Butler? And, two, will he be a part of the starting lineup against Boston? Obviously, with Crowder’s current injury, Milwaukee won’t get its answer on Wednesday in the first segment of Bucks-Celtics this season.  

Then there’s Beauchamp, who has captured the attention of many Bucks fans. He has the size, length and athleticism to theoretically defend at a high level, but asking him to guard superstars is a tough task for a second-year player. Andre Jackson Jr. has likewise shown great defensive promise, but it seems even more unlikely that he would be able to compete at that high of a level as a rookie.

For Boston, it is debatable whether Holiday is a step up from Smart defensively. Given his ability to guard taller players, however, he is the better defender. What’s not debatable is that Holiday is an offensive upgrade. He averaged 19.3 points and 7.4 assists per game last year. Smart averaged 11.5 points and 6.3 assists.

Milwaukee found a player that will help alleviate problems it has been having offensively for years. Boston got a player who is an upgrade over their previous point guard, but not necessarily better than Lillard. 

Overall, Lillard is the better player. 

Rivalry history 

The modern rivalry between these two teams dates back to 2018. There have been high-stakes games between the two organizations long before then, like the 1974 NBA Finals in which Boston defeated Milwaukee in seven games. The current cast of stars have been going head-to-head in highly contested games for five years now.

Antetokounmpo and Khris Middleton were the Bucks’ two best players then, and they have been the leaders in Milwaukee for the last five years. Likewise, Tatum and Brown were major players for Boston then, and certainly are now. 

In 2018, Terry Rozier crossed-up Eric Bledsoe and gave Boston a three-point lead with half a second to play in Game 1. Middleton proceeded to drill a shot from nearly half-court to force overtime. The Celtics ultimately won the game and went on to capture the series in seven.

In 2019, the Celtics emphatically defeated the Bucks in Milwaukee 112-90 in Game 1 of the Eastern Conference Semifinals. Paul Pierce famously went on air to say, “I think it’s over,” as he stated that he believed the Celtics would win the series.  The series certainly wasn’t over. Milwaukee went on to win four straight and take the series in five games.

Then most recently in 2022, the two teams met in the Eastern Semis again. Middleton missed the series due to injury, but Milwaukee still played great. Despite taking a 3-2 series lead with Game 6 in Milwaukee, the Bucks lost two straight and dropped to the Celtics in seven.

Now, some of the same faces are back. Antetokounmpo. Tatum. Middleton. Brown. Holiday. But there are some new faces as well, and some interesting storylines waiting to play out. If there is another postseason installment of this rivalry, it’s sure not to disappoint.

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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