It was early March 2023, and Giannis Antetokounmpo’s broad smile filled a box during a video call. The two-time MVP had joined us from Milwaukee’s practice facility, relaxed and contemplative as he rocked back and forth in a chair in the conference room, answering 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 had helped Antetokounmpo capture Milwuakee’s first championship in 50 years.
“He’s a hooper. He’s a hooper, man,” Antetokounmpo told Yahoo Sports. “He takes some shots that make you think, ‘God, how the hell does he take this shot?’ He excels in areas of the floor where people normally don’t excel. He’s really good in places on the floor where defenders are usually slower and relaxed because they know it’s not a good spot for you.” And then Antetokounmpo took his praise to another level, turning his nose up with as much reverence for Holiday’s humanity as he did his ability. “He’s a great leader. He played aggressively with the right tempo. He is now in his prime. Not only offensively, but also defensively he is a beast. That makes him great. You see a lot of people who can give you 20 every night offensively, but defensively they’re not that good. Jrue is always on, every night. His defense is always on and ready to go. I love playing with him, I love just putting on my shoes and playing a game with him. But most importantly, I just love what a wonderful human being he is. I love being around him.”
All that love for Holiday, the 6-foot-4 bulldog stripping Devin Booker and Antetokounmpo throwing a comic book lob in Game 5 of the 2021 NBA Finals was all part of what Milwaukee seemed 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 waking up from an afternoon nap. There was no early word, no warning, as Milwaukee and Portland were secretly working on a blockbuster deal that would trade Holiday for Portland Trail Blazers star Damian Lillard.
“The only reason 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 got traded. I’ve been randomly traded before. I know it’s part of it,” Holiday told Yahoo Sports. “You just have to deal with it. I’m not sure I really processed that. I’ve been so trapped in this [Celtics] team and try to win.”
After nominally living on Portland’s cap sheet that weekend, the Blazers redirected Holiday to Boston, where he has only raised the Celtics’ already sky-high ceiling as championship contenders. Holiday has connected on a career-best 43.5% of his triples for the Eastern Conference’s 60-win runaway star, untroubled by the fewest shooting attempts since his rookie season and still eager to flank the opponent’s most dangerous scoring threats. It’s no wonder there was widespread interest around the league in landing Holiday when Portland’s front office made it clear that the Blazers, as most rival teams expected, wouldn’t keep the veteran for long.
When Holiday left New Orleans for Milwaukee in 2020, David Griffin’s group worked with Holiday’s representation to find a suitable situation, one that both met the Pelicans’ price and placed Holiday in a competitive environment ended up. Blazers general manager Joe Cronin offered Holiday the same collaborative approach to finding his newest home last fall.
“It was mainly Portland being as transparent as possible and really asking me and being super honest with both sides and doing the best they could,” Holiday said, “but at the same time getting everything they wanted. I certainly appreciate everyone there.”
Initial interest was limited to selected teams. Philadelphia, where Holiday was drafted in 2009, approached Portland about a potential three-team scenario, sources said, as the Sixers navigated their own trading circumstances surrounding James Harden. Philly’s All-Star point guard had his eyes and beard on the Clippers, and Holiday seemed like a good fit next to Tyrese Maxey in Philadelphia’s backcourt. Still, as with their talks about moving Lillard, the Blazers made it clear that any deal with the Sixers would require Maxey to be netted. Portland prioritized emerging players with an eye on a return to Western Conference competition sooner or later.
The Clippers pursued Holiday on their own, sources said. At that point, Los Angeles’ attempts to land Harden from Philadelphia had reached a stalemate. The Clippers’ long-standing quest to find a premier guard alongside Kawhi Leonard and Paul George had not yet been fulfilled. They almost traded for Malcolm Brodgdon during the NBA Draft after tracking him for several seasons. Holiday would have served as another intriguing matchup. Holiday, a UCLA product and Los Angeles native, still maintains a home in Southern California. More than half of his 10 acres sprout avocados twice a year. A staff comes to harvest the trees. “Honestly, I just liked the country,” Holiday said. “And the avocados make money.”
His family is still made up of Lakers fans. Holiday had gotten into a car with friends and loved ones and headed to a Dodgers game in June 2013 when Sam Hinkie called to let Holiday know he was being transported from Philadelphia to New Orleans. His latest trade saga came to an end with Boston’s package that provided Portland with draft capital – two first-round picks – plus an experienced guard in Malcolm Brogdon and a young center in Robert Williams III. And the Celtics found a former playoff pest who could fill their new hole in the backcourt after Boston traded Marcus Smart to the Grizzlies. “He’s been one of the best defensemen in the league for a long time,” head coach Joe Mazzulla said.
While Holiday got 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 feel about the game and see how he feels about the game,” Mazzulla said. “And we just have a shared mental model of how to process the game 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 take away the opponent’s biggest strength. Whether that is over the course of an entire match or during one specific match.”
With the Bucks, Holiday was primarily assigned to the opposing lead guards, having to sneak his way up and around and bruise the fencers 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 did one or two different things. But here, every kind of defense you can think of, we probably did,” Holiday said. “Just thinking about the game, looking at matchups, seeing how we can get teams out of timeouts. Even playing outside the boundaries, [sideline out of bounds], whatever it is. I just try to look at the game and think about it differently.”
Holiday, 34, became eligible for a contract extension on April 1 and has a $37.4 million player option for next season. There’s still plenty of room for his continued two-sided brilliance, and perhaps an appearance at the Olympics this summer as well. Holiday himself started a rumor about his impending retirement — “just talking s***” — on the Point Forward podcast, hosted by his former Sixers teammates Andre Iguodala and Evan Turner, but after the Celtics’ win in Charlotte that Monday night (118-104). Holiday said he has no vision of quitting “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 dressing after his team-high 25 points. “I’m thinking about that cheese!” Tatum screamed. “He’s thinking about that money!”
To his credit, Holiday is only thinking about June. He claims there will be no added spice or spice if Boston ties Milwaukee in the postseason, where the second-seeded Bucks loom as a potential foe in the Eastern Conference finals. “I want to beat them,” Holiday told Yahoo Sports, “because I want to win the championship.”