Fact or Fiction: Did the Milwaukee Bucks win the Damian Lillard-Jrue Holiday trade?

Each week during the 2023-24 NBA season, we will take a deeper dive into some of the league’s biggest storylines in an attempt to determine whether the trends are based more in fact or fiction moving forward.

This week's topic: The Bucks won the Damian Lillard-Jrue Holiday trade

BOSTON — One minute into a Thanksgiving eve showdown between the two Eastern Conference favorites, Celtics guard Jrue Holiday picked up former Milwaukee Bucks teammate Giannis Antetokounmpo on the defensive end, getting a hand on the two-time MVP's layup attempt and igniting a 10-0 run out of the gate.

Later in the opening quarter, Boston's Kristaps Porziņģis received a pass at the free-throw line, realized he was defended by Bucks guard Damian Lillard and backed him into the paint, drawing a pair of free throws.

The changes to both teams since last they met were immediately apparent, and they did not fall in Milwaukee's favor. It is early. It is one game. Bucks forward Jae Crowder is sidelined for eight weeks. They are 15 games into first-year head coach Adrian Griffin's career. But, man, the talent deficit here was stark.

The Celtics never trailed, pushed the lead to 20 points in both halves and maintained a double-digit lead for the vast majority of the game — until a late Bucks 12-2 run briefly cut the deficit to one possession inside the final minute. Milwaukee guard Malik Beasley's last-second 3-pointer settled the final score at 119-116.

The Bucks left the game heartened by the rally. If not for that initial 10-0 hole, they said. If not for so many missed opportunities around the rim. If not for Boston's shooting. If not for Antetokounmpo's inefficiency.

Still, there is no excusing what is clear: Between Holiday and Derrick White, the Celtics boast the NBA's best defensive backcourt in the NBA, and between Lillard and Beasley, the Bucks ... well ... do not.

Defiance or otherwise, Lillard was not all that worried about this reality, at least not on this night.

"I didn't think they pressured me," the veteran said. "They're a really good defensive backcourt, but I wouldn't say they were pressuring or anything like that. They're just solid, they've got good size, they're strong, they're smart and they compete on that end of the floor, but I didn't feel pressured or anything."

It does not help him that every member of Boston's eight-man rotation is dangerous from deep, drawing Antetokounmpo and Brook Lopez away from the rim, further weakening the heart of Milwaukee's defense.

Asked whether that dynamic forces adjustments, Lopez said, "Of course. They make it tough. We've got to trust everyone. It's not just going to be myself or Giannis or whoever. It's going to be at the rim. There are situations where we can maybe try to read it and be there, but we're all going to have to rely on each other."

Barring injuries, those hard truths are not going to significantly change between now and the playoffs.

Milwaukee Bucks guard Damian Lillard (0) drives to the basket defended by Boston Celtics guard Jrue Holiday (4) during the second half of Wednesday's game. (Paul Rutherford/USA Today Sports)
Milwaukee Bucks guard Damian Lillard (0) drives to the basket defended by Boston Celtics guard Jrue Holiday (4) during the second half of Wednesday's game. (Paul Rutherford/USA Today Sports)

The Bucks traded Holiday, Grayson Allen and the rights to three first-round draft picks to the Portland Trail Blazers for Lillard in late September, forging a new betting favorite to win the NBA championship. A few days later, the Blazers turned around and dealt Holiday to the Celtics, reestablishing them as the favorites.

As Holiday said at shootaround, "I think [the Bucks] got what they wanted, so I can't be mad at that. A warning would've been cool, but other than that, I'm in the best place I can be to compete against them."

"Weird feeling to play against [Holiday], for sure, and very tough that he's not with the team anymore, but life moves on," Antetokounmpo said after totaling 21 points, 13 rebounds and five assists in defeat. "Do I feel like we lose something? For sure. We lose Jrue Holiday. He's been a great player in the league for a lot of years, a winner, a good teammate, so we definitely lose that, but at the end of the day, we have great players on our team now that can step up and not only fill the void but carry that torch and do better."

The question floating around league circles in the immediate aftermath of both deals: Would the Bucks have made the trade if they knew Holiday would land on their chief competitor to reach the Finals? The common refrain was yes, they would, because Antetokounmpo obviously approved of the trade, and within several weeks he signed the three-year, $186 million contract extension he had previously said would stay on hold.

Losing Antetokounmpo would have crippled the franchise, but that answer does not resolve the fact that dealing for Lillard made Milwaukee's perimeter defense worse and tied a neat bow on Boston's offseason.

The Celtics traded stalwart defensive guard Marcus Smart for Porziņģis in June. That left a backcourt hole that would have otherwise been filled by an unhappy Malcolm Brogdon, who Boston flipped with Robert Williams III for Holiday — arguably a better defender than Smart and inarguably the better offensive player. The net gain: Porziņģis, Holiday and a starting lineup that owns a +27 net rating over almost 200 minutes.

"They're really good," Antetokounmpo said. "They're really good. They play the right way. They're playing for one another. They have multiple guys that can shoot from the 3-point line, guys that want to get going offensively. Now they also have great bigs that can space the floor and create more gaps for White, [Jayson] Tatum and [Jaylen] Brown, so yeah, they've been always good, and this is another year that they're very, very good."

Milwaukee, on the other hand, ranks 22nd in defensive rating (115.6 points per 100 possessions) a season removed from fielding a top-five outfit. They remade their defense under Griffin five games into the season, reverting to the old regime's drop-coverage scheme that freed Lopez to protect the rim. Their defense has been marginally better since, and while they posted a 113.4 defensive rating over the five-game winning streak that they carried into Wednesday's game, four of those victories came against bottom-12 offenses.

The Celtics are a different animal. They shot 52.4% from the field and 40.5% from deep. More specifically, they finished 21 for 23 at the rim (91.3%) and 5 for 5 on corner 3s. Some say 57 points on 28 shots is good.

"We've got to be better," Antetokounmpo added. "They want to shoot a lot of 3s. They get comfortable by shooting 3s. They play well when they shoot 3s, and then they're able to break down your defense and drive the ball, get in the paint and kick it out for another 3. We've got to do a better job defending the 3-point line, keeping guys in front of us, and hopefully next time when we play them, we can do that."

The Bucks got what they expect from Lillard (27 points, five rebounds and five assists) in the loss. Holiday finished with just five points on 1-for-8 shooting, eight rebounds and one assist against a pair of turnovers.

This is not about counting statistics. It is about the upgrade from Holiday to Lillard in Milwaukee vs. that of Brogdon to Holiday in Boston, and what that means for what feels like their inevitable playoff showdown.

"If we're going to complete our goal of winning a championship, we're obviously going to have to meet up with them at some point," said Lopez, whose game-high 28 points (12-of-18 FG, 2-of-5 3P) should be a concern for Boston. "They're a very talented team with the same aspirations. As long as we take care of business, keep improving game in and game out, I'm sure we'll run into them, and we'll see what it's like then."

The mere presence of Lillard and Antetokounmpo — two all-time great players — means there is no team they cannot beat, but over a seven-game series, the margins matter, and Milwaukee's weakened perimeter defense against Boston's revamped five-out offense full of two-way players is an awfully wide one to close.

Determination: Fiction. The Lillard-Holiday trade inadvertently made the Celtics stronger than the Bucks.