The Milwaukee Bucks’ colossal November 2020 trade for Jrue Holiday has already paid off in full, as far as that franchise is concerned. The Bucks pushed their chips into the middle of the table in November 2020, and as a result, walked away with a championship. Eric Bledsoe, two first-round picks and two first-round pick swaps are an easy price to pay for a ring.
In a twist of fate, though, while Holiday was an instrumental piece in Milwaukee’s championship run, he’s perhaps never faced more pressure during his time with the Bucks than he will in the second round of the 2022 NBA Playoffs.
The Boston Celtics enter this second-round matchup with one crucial advantage: the Bucks will likely be without the services of All-Star wing Khris Middleton for the entire series. It’s a significant loss. Alongside Giannis Antetokounmpo, Middleton is one of the twin engines that powers the Milwaukee offense — a reliable 20-point scorer and proven playoff performer (and known Celtic-killer) who can carry the scoring load during the Bucks’ occasional dry spells.
The need to fill such a significant void is Milwaukee’s greatest pressure point in this series, and the Celtics’ biggest opportunity. Some combination of Grayson Allen, Pat Connaughton, Wes Matthews and (when healthy) George Hill will assume the minutes left over by Middleton’s injury. That is a competent group of effective role players, but they’re also not a sufficient replacement for Middleton’s significant value.
That brings us to Holiday, who has quietly become the most fascinating figure in the Celtics-Bucks equation. One of the perks of his fit alongside two established scorers was how it reduced his offensive burden, freeing him to focus on locking teams down on the defensive side of the ball. His 22.9% usage rate in 126 regular season games with the Bucks would be the lowest he’s recorded since he was a 21-year-old the Philadelphia 76ers, and he’s responded with 50/40/77 splits in that span of time.
With Middleton likely out for the entire second round with a sprained MCL, he’s now the de facto number two scoring option in the Milwaukee offense. This will be the first time he’s filled such a significant role for a playoff team since the 2017-18 New Orleans Pelicans (post-DeMarcus Cousins injury). That remarkable regular season efficiency is going to be put to the test as he’s asked to assume a markedly more prominent burden in their offensive scheme.
It’s also worth noting that, while Holiday was terrific overall for the Bucks last postseason, he left something to be desired as a scorer. His efficiency cratered, dropping from a sterling 59.3% true shooting percentage in the regular season all the way down to 48% through the playoffs. In the NBA Finals, he shot just 36% from the field. These were bafflingly poor shooting performances from a guy who, while far from being considered an elite scorer, has always been a reliable one.
From Milwaukee’s perspective, Holiday simply cannot be that inconsistent offensively in this series. Every bricked shot gains yet more importance when they no longer have the Middleton safety valve to break out of cold stretches. Thus far, the Bucks haven’t lost since Middleton went down, but Holiday has been merely okay; a big 26-point, 5 made threes Game 4 against Chicago covered up a relatively tame 43/35/50 shooting split in Games 3 and 4.
That “against Chicago” leads us to our point of interest. The Bulls are a completely different ballgame than this Boston Celtics defense. How about we add Marcus Smart, Derrick White and the best defense in basketball to the mix?
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Photo by Jim Davis/The Boston Globe via Getty Images
From the Celtics’ perspective, frustrating Holiday should be seen as a goal. And it just so happens that they have the right men for the job in their newly anointed Defensive Player of the Year and the crown jewel of their trade deadline. This is a defense that rendered Kyrie Irving nearly anonymous across the final three games of their first-round sweep, and Holiday isn’t in the same tier as a number-two scorer.
Holiday’s significantly increased importance to the Milwaukee offense could also come at a price on the other end, where he also operates as their best perimeter defender. He’s on the shortlist (alongside Smart) for the best guard defenders in basketball, strong and rangy, with incredible awareness and instincts on that end of the floor.
Enter Jaylen Brown, who, with Middleton gone, would presumably become one of Holiday’s most frequent assignments. Brown himself is a question mark as the series gets going, after struggling with hamstring tightness late in the series-clinching win against Brooklyn. Assuming he plays, though, he offers a significant complication for the Milwaukee defense; where Middleton likely would have spent time on Brown under normal circumstances, the Bucks may very likely have to stick Holiday to him more often, sacrificing some of his valuable versatility in the process. Holiday is the kind of defender who can overcome a size differential, but Brown is a particularly tough ask given his hyper-athleticism and physicality.
During media availability on Friday, Holiday contrasted the challenges of defending Tatum and Brown against Chicago’s Zach LaVine and DeMar DeRozan.
“I think they get rhythms from playing outside of the [three-point line] … Jayson and Jaylen have that kind of step-back, lull you to sleep around the three-point line, which makes them a little bit more deadly.”
When asked about Middleton’s absence on the defensive end of the court, Holiday gave a glimpse into the challenges the Bucks’ defense will face in the series.
“Sometimes without Khris, we have another guy we’re not gonna switch with and it gets tricky, and they get a three or a layup,” he said. “I think with Khris out there, we kind of have a little more leeway in terms of whether we want to switch or not switch.
Overall, Jrue Holiday stands as a likely inflection point for both teams in this series. Jayson Tatum and Giannis Antetokounmpo are the headliners for a reason, and they’re going to command the most attention as the second round progresses. But a best-of-seven matchup between two teams on this level will be decided on the margins, and how the Celtics can take advantage of Holiday’s increased responsibility could tell the story of how this series plays out.
