How Jrue Holiday has seamlessly fit in with the championship favorites

It was early March 2023, and Giannis Antetokounmpo’s wide smile filled a box on a video call. The two-time MVP had joined us from Milwaukee’s practice facility, relaxed and contemplative as he rocked in a conference room chair, fielding questions ranging from his secret pre-draft visit to Atlanta a decade earlier, to his appreciation for teammate Jrue Holiday, the All-Star point guard who’d helped Antetokounmpo capture Milwuakee’s first championship in 50 years.

“He’s a hooper. He’s a hooper, man,” Antetokounmpo told Yahoo Sports. “He makes some shots you’re just like, ‘God, how the hell is he making this shot?’ He excels in spots on the floor that usually people don’t excel at. He’s really good in spots on the floor where the defenders are usually slowing down and relaxed because they know it’s not a good spot for you to be.” And then, Antetokounmpo took his praise to another level, scrunching his nose with reverence for Holiday’s humanity as much as his ability. “He’s a great leader. He’s been aggressive playing with the right pace. He’s in his prime right now. Not only offensively, but defensively he’s a beast. That’s what makes him amazing. You see a lot of people who can give you 20 any given night offensively, but defensively they’re not as good. Jrue is always on every given night. His defense is always on and ready to go. I love playing with him, I love just lacing up my shoes to go compete in a game with him. But most importantly, I just love what a great human being he is. I love being around him.”

All that love for Holiday, the 6-foot-4 bulldog who stripped Devin Booker and threw Antetokounmpo that comicbook lob in Game 5 of the 2021 NBA Finals, was all part of what made Milwaukee seem like the final destination of Holiday’s career. It’s part of what made the call from Holiday’s agent later that September all the more surprising, in addition to his early dizziness from being stirred from an afternoon nap. There was no early word, no warning, as Milwaukee and Portland worked in secret on a blockbuster that would swap Holiday for Portland Trail Blazers star Damian Lillard.

“The only reason why I think it was tough was because it was a shock. That’s the only reason I was surprised. I’m not necessarily surprised because I was traded. I’ve been traded randomly before. I know it’s a part of it,” Holiday told Yahoo Sports. “You kinda just deal with it. I’m not sure if I have really processed that. I’ve been so locked into this [Celtics] team and trying to win.”

After he spent that weekend nominally residing on Portland’s cap sheet, the Blazers rerouted Holiday to Boston, where he has only raised the Celtics’ already towering ceiling as championship contenders. Holiday has drilled a career-best 43.5% of his triples for the 60-win, runaway top seed of the Eastern Conference, unbothered by the fewest shooting attempts since his rookie season, still eager to flank opponents’ most dangerous scoring threats. It’s no wonder there was widespread interest around the league in landing Holiday once Portland’s front office made it clear, as most rival teams expected, the Blazers wouldn’t be holding on to the veteran for very long.

When Holiday exited New Orleans for Milwaukee in 2020, David Griffin’s group worked in concert with Holiday’s representation to find a suitable situation, one that both satisfied the Pelicans’ price point and landed Holiday in a contending environment. Blazers general manager Joe Cronin afforded Holiday the same collaborative approach to find his latest home this past fall.

“Mainly it was just Portland being as transparent as possible and really asking me and being super honest with both parties and doing the best that they could,” Holiday said, “but at the same time, getting everything that they wanted. I definitely appreciate everybody over there.”

The initial flurry of interest got whittled down to select teams. Philadelphia, where Holiday was drafted in 2009, approached Portland about a potential three-team scenario, sources said, while the Sixers were navigating their own trade circumstances surrounding James Harden. Philly’s All-Star point guard had his eyes and beard set on the Clippers, and Holiday seemed like a strong fit next to Tyrese Maxey in Philadelphia’s backcourt. Yet the Blazers, as with their conversations on moving Lillard, made it clear any deal with the Sixers would require netting Maxey. Portland was prioritizing rising players, with an eye toward bouncing back into competition within the Western Conference sooner rather than later.

The Clippers pursued Holiday in their own right, sources said. At that juncture, Los Angeles’ efforts to land Harden from Philadelphia had reached a stalemate. The Clippers’ longstanding quest to find a premier guard next to Kawhi Leonard and Paul George had yet been fulfilled. They’d nearly traded for Malcolm Brogdon during the NBA Draft after tracking him for several seasons. Holiday would have served as another intriguing fit. A UCLA product and Los Angeles native, Holiday still keeps a home in Southern California. More than half of his 10 acres sprout avocados twice a year. A staff comes and harvests the trees. “I just liked the land, honestly,” Holiday said. “And the avocados make money.”

His family is still made up of Lakers fans. Holiday had piled into a car with friends and loved ones, shuttling to a Dodgers game in June 2013, when Sam Hinkie phoned to let Holiday know he was being dealt from Philadelphia to New Orleans. His latest trade saga came to a conclusion with Boston’s package that both supplied Portland with draft capital — two first-round picks — plus a veteran guard in Brogdon and a young center in Robert Williams III. And the Celtics found a former playoff pest that could fill their new hole in the backcourt after Boston traded Marcus Smart to the Grizzlies. “He’s one of the best defenders in the league for a long time,” head coach Joe Mazzulla said.

As Holiday gathered his bearings, Mazzulla sent him a collection of defensive clips. “I really just wanted to build a connection and get on the same page about how we think the game and see how he thinks the game,” Mazzulla said. “And just kinda have that shared mental model about how the game can be processed in real time and different things that we can go to at different times to be able to take advantage of what we have, or to take away the opponents’ biggest strength. Whether that’s over the course of an entire game or on one particular play.”

Boston Celtics guard Jrue Holiday (4) in the first half of an NBA basketball game Thursday, March 7, 2024, in Denver. (AP Photo/David Zalubowski)
Celtics guard Jrue Holiday is focused on how he can help Boston win a championship. (AP Photo/David Zalubowski)

With the Bucks, Holiday was predominantly assigned to opposing lead guards, having to slither his way up and around bruising screeners on possession after possession. With the Celtics, he has guarded everyone from Donovan Mitchell to Julius Randle and Joel Embiid. “Where I came from, we kinda did one or two different things. But here, any type of defense you can think of, we’ve probably done it,” Holiday said. “Just thinking the game, looking at matchups, looking at how we can disrupt teams out of timeouts. Even out-of-bounds plays, [sideline out of bounds], whatever it is. Just trying to look at the game and think it differently.”

Holiday, 34, became eligible for a contract extension April 1 and holds a $37.4 million player option for next season. There’s still plenty of runway for his continued two-way brilliance, with perhaps another appearance in the Olympics coming this summer as well. Holiday himself started a rumor about his imminent retirement – “just talking s***” – on the Point Forward podcast hosted by his former Sixers teammates Andre Iguodala and Evan Turner, but after the Celtics’ 118-104 victory in Charlotte that Monday evening, Holiday said he has no vision of calling it quits “until my kids tell me not to [play]. Until Jayson tells me not to.”

Two lockers to Holiday’s right, Celtics All-Star Jayson Tatum was finishing dressing following his team-high 25 points. “Thinking about that cheese!” Tatum screeched. “He’s thinking about that money!”

Holiday, to his credit, is only thinking about June. He claims there will be no extra juice or spice if Boston draws Milwaukee in the postseason, where the second-seeded Bucks loom as a potential Eastern Conference finals foe. “I want to beat them,” Holiday told Yahoo Sports, “because I want to win the championship.”