According to Holiday, the real challenge during Celtics practices was Payton Pritchard. The two-time NBA champion named the relentless backup guard as the one who gave him the most trouble in full-court drills.

“It might be Payton [Pritchard],” Holiday said on Run It Back TV. “There’s this drill that we have where you have to dribble against Payton full-court. He just be going crazy. Speed, handle, low to the ground so he could body you. Stops on a dime. Payton’s cold, bro.”

Holiday spent two seasons in Boston, averaging 11.8 points, 4.9 rebounds, and 4.4 assists per game while shooting 46.4 percent from the field. As the Celtics’ starting point guard, he helped lead them to the 2024 championship — just three years after lifting the Larry O’Brien Trophy with the Milwaukee Bucks.

Unfortunately, Holiday’s run with the Celtics recently came to an end following his trade to the Portland Trail Blazers this preseason. The move was a tough blow for Boston’s roster, but the front office chose to cut salary after a string of injuries derailed their title hopes heading into the 2025-26 campaign.

The Celtics, however, managed to keep Pritchard, a decision that looks increasingly valuable. Last season, he averaged 14.3 points, 3.8 rebounds, and 3.5 assists in a career-high 28.4 minutes per game. He carved out a sizeable role as one of the first options off the bench and became an integral part of their rotation. Now, he is gonna be more important with the absent of Jayson Tatum and could be a great partner of Brown.

His role only grew in importance over the course of the year, culminating in recognition as the NBA’s Sixth Man of the Year. Pritchard’s consistent and selfless scoring was paired with disruptive defense, which Boston regularly used in practice to sharpen their stars’ ball-handling skills.

For Holiday, the impression was clear: Pritchard is more than a spark plug. In his eyes, the Celtics have a “secret weapon” in the scrappy guard — a player whose value extends well beyond the box score.

In late June, the Celtics traded Holiday to the Portland Trail Blazers, ironically sending him back to the city he briefly called home before his 2023 arrival in Boston. The two-time All-Star made a massive impact in Beantown, helping the Celtics capture their record-setting 18th NBA championship less than a year after joining the franchise.

Holiday now brings his championship pedigree to Portland, a city still searching for its first NBA title since 1977. Meanwhile, White must move forward without his veteran backcourt partner as Boston heads into a new season marked by uncertainty.

Speaking on the White Noise Podcast, White acknowledged how much the Celtics will feel Holiday’s absence. “We’ll definitely miss him,” White said. “You can’t really replace a Jrue Holiday.”

Together, White and Holiday formed arguably the NBA’s most formidable defensive backcourt last season. Both earned spots on the NBA All-Defensive Second Team in 2024 and routinely shut down opposing guards with physicality and discipline.

White also credited Holiday for his own offensive breakout, noting how the veteran guard was willing to take a step back and let others thrive. “Jrue allowed me to be me,” White explained. “Allowed me to kind of step into my own and do what I do.” He also highlighted Holiday’s all-around game and versatility as a major asset to the team.

White will now be tasked with elevating his game even further if the Celtics hope to remain NBA contenders. Boston not only lost Holiday this offseason but also saw starting center Kristaps Porzingis and backup big man Luke Kornet depart. To make matters worse, Tatum is now sidelined indefinitely with an Achilles injury, adding even more pressure on the remaining core.

Shams Charania broke the news on X, detailing what Tatum’s team had just done: “The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN.” The post quickly gained traction, racking up nearly 700,000 views.

Jrue Holiday‘s contributions this season included averaging 11.1 points per game over 62 contests playing alongside Jayson Tatum. He ranked fourth among Celtics players in games played and was a crucial component of their 2023-24 NBA championship run.

Strong Social Media Reaction to Trade

The reaction on X (formerly Twitter) and other social media platforms was swift and significant. Most comments expressed gratitude to Holiday for his role in securing an NBA title. However, others voiced confusion over the trade and questioned how the Celtics could benefit from the move.

“None of this was ever going to be pretty but Simons is a bonafide 20 pt shooter/scorer and he fits in Jays age range,” Celtics fan Derrick Washington posted on X. Another fan remarked, “What was the reason for trading a very good, promising 26 year old + 2 second round picks for an aging Jrue Holiday. Makes no sense for the Blazers..“

Holiday’s Earnings with the Celtics

Holiday’s pockets were certainly well-lined during his tenure in Boston, as the franchise paid him $67,670,347 for his years of service with the team. While his time was relatively brief, it proved to be financially lucrative for him.

The Celtics had the third-highest payroll in the league this year, at over $195 million, trailing only the Phoenix Suns and the Minnesota Timberwolves. Projections for the 2025–26 season show that number increasing to more than $223 million—potentially the highest in the NBA. That’s why there’s speculation they may need to unload part of that amount.

According to NBA insider Shams Charania, the franchise’s plan is obviously to keep Tatum, but also stars like Jaylen Brown and Derrick White, despite interest from other teams. However, that stance could change if a strong enough offer comes along.

Given that context, another player is now being considered as a potential departure. Holiday earns $32.4 million annually, with two more years on his contract and a player option for 2027–28. That makes him a logical option if the team decides to move on from a current roster member.

Where could Holiday land?

According to NBA reporter Marc Stein, Jrue Holiday’s next destination could be in the West: the Sacramento Kings are evaluating several point guard options to strengthen the team’s playmaking after De’Aaron Fox’s departure to the San Antonio Spurs in February.

Holiday is reportedly on the Kings’ radar as a viable target—something that could align with Boston’s potential willingness to move him. Still, he’s not the only option: Washington Wizards’ Marcus Smart has also been mentioned, along with Malcolm Brogdon.

What do the Celtics lose without Holiday?

Since arriving in Boston from the Milwaukee Bucks in 2023, Jrue Holiday has been a consistent piece in head coach Joe Mazzulla’s game plan. Over the past two seasons, the guard has started every game he’s played, both in the regular season and the playoffs.

This year, Holiday averaged 30.6 minutes across 62 games, putting up 11.1 points, 4.3 rebounds, and 3.9 assists. He maintained a key role in the postseason as well, starting all eight games against the Orlando Magic and the New York Knicks, with averages of 9.5 points, 4.1 rebounds, and 4.0 assists.

It’s clear that the potential departure of Jrue Holiday would present a challenge for Mazzulla as he plans next season’s roster. Part of the solution might involve giving a more prominent role to Payton Pritchard, who stood out this season as a key part of the rotation—so much so that he won the Sixth Man of the Year award.

According to NBA insider Marc Stein, general manager Nico Harrison is exploring trade options to strengthen the backcourt. He has set his sights on three players: Jrue Holiday, Lonzo Ball, and Chris Paul. The Mavericks show strong interest in Holiday, but his $104 million contract makes a deal difficult. For this reason, Ball and Paul could be easier options offering valuable experience at a lower financial cost.

These moves could lead to the departure of P.J. Washington, as per Shams Charania. The 26-year-old still has a year left on his contract and carries strong trade value. For that reason, Harrison may look to move him in a package deal to secure one of the experienced guards. This decision help strengthen the Kidd’s roster depth and build a team capable of contending.

Adding Cooper Flagg and a veteran guard would address both immediate needs and long-term goals. The front office wants experienced players who can contribute right away. At the same time, they aim to protect the team’s future by blending youth with leadership and experience.

Could Jrue Holiday, Lonzo Ball, or Chris Paul significantly elevate Mavs’ performance in the next season?

If the Dallas Mavericks want a front-line player to strengthen their roster, Jrue Holiday, Lonzo Ball, or Chris Paul might not be ideal for many Mavs fans. Holiday, despite playing for the top-seeded Boston Celtics, faced steady criticism this season. His production dropped to 11.1 points, 4.3 rebounds, and 3.9 assists per game. In fact, those are his worst numbers since his rookie year, raising concerns about his fit in Dallas.

Meanwhile, Lonzo Ball brings just as much uncertainty. His knee injuries have kept him out for two full seasons, and the risk of re-injury remains high. After a turbulent year heavily affected by injuries, the Mavericks need stability. However, Ball is the youngest of the three options. If he manages to stay healthy, he could fit well under Jason Kidd’s system and bring much-needed energy to the backcourt.

Chris Paul, on the other hand, comes with fewer questions about his health and contract. Despite turning 40, he played 82 games this season and proved he can still contribute. Still, his age and inconsistent performances create doubt about his ability to keep up in the postseason. For a team that aims to compete at the highest level, this remains a valid concern.

Each of the three players presents a different kind of risk. Their profiles raise questions that the Mavericks must weigh carefully. Yet, if the goal is to add reliable depth, all three could offer value in specific roles.

“I think that we still have a really great opportunity and a great window to be successful, and win a championship again,” Holiday said during a Saturday press conference in Boston. “I think the talent that we have on this team, not only on the court but the coaching staff… the opportunity to win is now and I still want to be a part of that.”

With those clear words, Jrue made his intention to stay with the Celtics for a third consecutive year known. However, he also acknowledged that the decision isn’t entirely in his hands. “I think the things that I can control, I do my best to control. But other than that, I try my best not to worry about it,” he said.

“So for me, offseason, having a little break, getting back right and preparing for next season is all that I could really do. Who comes back, roster changes and things like that, it’s not really in my control. So I just focus on what I can,” added the guard, who played in 62 regular season games and 8 playoff games this year.

Holiday feels the Celtics came up short

Much of the motivation Holiday expressed for staying in Boston stems from his belief in what this team can achieve moving forward, based on what they’ve built over the past two NBA seasons. “I think that we had the best team in the league,” he said.

That’s why the loss to the Knicks was such a bitter disappointment. “It’s a lost opportunity,” Jrue admitted. “The chemistry that we had, that we built from last season, even coming into this postseason and how we were feeling, I feel like we are disappointed in ourselves. We felt like we let the organization down and the city down.”

Credit to the Knicks, according to Holiday

Despite his disappointment with Boston’s early exit, Jrue Holiday also gave credit to New York for earning their spot in the Eastern Conference Finals. “I think going against a team like the Knicks, who play hard and will always give themselves a chance, hats off to them. They played very well,” the guard said.

“I can’t necessarily say that there was anything that we did or didn’t do,” Holiday added. “I think most of the games we played, we were up quite a bit. We are a team who down the stretch executes pretty well, we’ve seen it last year. We’ve seen it throughout the season this year. That’s why we’ve won so many games, but sometimes you figure things happen and it didn’t go our way.”

In a recent conversation on the Podcast P with Philadelphia 76ers star Paul George, Holiday was asked a direct question: “$50 million. Cash money. You get 7 months to train, Jake Paul calls you out, you taking the fight?” Holiday’s reaction was priceless. “$50K?” he responded, initially seeming amused, before pausing and jokingly making a face.

“That really put things into perspective,” Holiday continued. “I’ll make it look realistic. That last little fight (Jake Paul vs. Mike Tyson), I don’t know nothing about nothing, but I could do that.” Jrue wasn’t shy in sharing his thoughts on the Tyson-Paul bout, making it clear he wasn’t impressed by what he saw inside the ring that night.

But the Celtics star didn’t stop there. He went on to detail how he’d prepare for such a hypothetical matchup against Paul. “We could pump it up a little bit, I could take him through my whole training camp and all that,” said the 34-year-old guard. “Once we get up there, Netflix will start messing up, so you can’t really see a lot of the fight. Now I’ll swing one time and he can hit me. Cool. $50 million.”

Jake Paul vs NBA players

If Jrue Holiday were to pursue the idea of stepping into the ring with Jake Paul, he wouldn’t be the first NBA player to face the controversial YouTuber-turned-boxer. In November 2020, Paul squared off against former NBA player Nate Robinson in Los Angeles, securing a dominant knockout victory in the second round of their six-round bout.

At the time, Robinson, 36, had been out of the NBA for five years following his final stint with the New Orleans Pelicans and had officially retired from basketball in 2018. In comparison, Jrue Holiday would present a much tougher challenge for Jake Paul. Standing at 6 ft 4 in, Holiday is notably taller than Robinson, who stands at 5 ft 9 in, and he’s also younger, being a couple of years younger than Robinson was when he faced Paul.

Holiday should stay in NBA

While the idea of Holiday in the boxing ring is intriguing, it’s clear that basketball remains his true calling. The 34-year-old guard has played 19 games for the Boston Celtics this season, averaging 11.7 points, 4.2 rebounds, and 3.9 assists per game. Holiday has been a vital contributor to the Celtics, especially when healthy, and has continued to play a significant role in head coach Joe Mazzulla’s rotation.

Former Miami Heat forward Udonis Haslem highlighted Bronny’s work so far, comparing him to Jrue Holiday. “He’s done a great job of just quieting the noise & focusing on the things he can control. When he speaks, he talks about being a Jrue Holiday type of guy. He can come in, and make an impact like that, ” Haslem said in The OGs Show YouTube channel.

Despite the criticism of his performance during the NBA Summer League, the truth is that Bronny shows promising qualities. At just 19 years old, he shows an athletic yet durable build, making him a challenge for smaller guards while also allowing him to navigate around slimmer, shiftier players.

Holiday’s similarities with Bronny

The three-time NBA winner with Miami Heat may have done a spot-on comparison. A lot of the best guards in the NBA referred to Jrue Holiday as the hardest defender in the league, while also having an amazing work rate without the ball, turning him in one of the best point guards.

Holiday didn’t truly hit his stride until his fourth season, when he earned a spot on the NBA All-Star team. From then on, his defense became exceptional, and his offensive game also significantly improved, leading him to win two Olympic gold medals (Tokyo 2020 and Paris 2024) and two NBA championships (2021 with Bucks and 2024 with Celtics).

Whether Bronny can live up to the expectations remains to be seen. He’ll have the opportunity to prove Haslem’s statement when the Lakers face the Minnesota Timberwolves in his first preseason game on October 4.

Paul has made it clear that he wants to do what’s best for the team and pursue a championship, but he didn’t seem too keen on the idea of coming off the bench. Needless to say, that could be an issue.

So, now that the Milwaukee Bucks have dealt Jrue Holiday to Portland and he’s seemingly up for grabs, Brian Windhorst of ESPN believes the Warriors could look to re-trade Paul to acquire him.

Warriors Could Be In The Mix For Jrue Holiday

“Even the Golden State Warriors, who have interesting young players on their roster, plus a few far-out draft picks and swaps when Stephen Curry might be retired, could join the race,” Windhorst said. “Provided they’d be willing to re-trade Chris Paul, who members of the organization have praised for his offseason work of trying to fit in.”

The Warriors have repeatedly stated that they have no intention to trade Paul and that they want him to be a part of the team. However, that was before a star like Holiday became available.

Besides being one of the most impactful defenders in the league, Holiday doesn’t have an ego, is more durable, and would give the Warriors a better shot at a championship at this point in his career.

Memphis Grizzlies star Jaren Jackson Jr. recently became the latest player to earn that distinction. He was another one-time winner after Marcus Smart got the nod in the 2021-22 season.

But there are still several defensive superstars that don’t seem to get the credit they deserve for their contributions. Here, we’ll talk about the three best active defenders that haven’t won DPOY yet.

Best Active NBA Players With No DPOY Awards

3. Anthony Davis

Anthony Davis might as well be the best rim protector in the Association. He can swat shots into the standings, and he alters the whole flow of the rival team’s offense when he’s looming around in the paint.

The Los Angeles Lakers star has never been named Defensive Player of the Year, most likely because he’s often hurt and has rarely played a full season. Otherwise, he’d have at least one of those.

2. Bam Adebayo

Bam Adebayo has been near the top of the Defensive Player of the Year rankings way too many times already. Just like with Joel Embiid and the MVP award, he’s often finishing second or third.

But the sole fact that Adebayo has made the podium more often than not in his career speaks volumes of his defensive impact. He’s one of the few bigs that can hold their own in the perimeter.

1. Jrue Holiday

Most NBA players agree that Jrue Holiday is the absolute best defender in the league, so the fact that he hasn’t even been a finalist for Defensive Player of the Year is baffling and mind-blowing for most.

Holiday is an absolute pest in the perimeter. He’s got quick hands to swipe the ball off any other players’ possession, not to mention he’s a pesky guy who’ll go over screens and can guard one through five.

With that in mind, GMs and coaches leave no stone unturned looking for those guys who can play lockdown D. So, if they can also hit the occasional three or be a positive factor in the offensive end of the floor, you better believe they’ll log plenty of minutes.

Those guys don’t often get the recognition they deserve, nor the big contracts they would’ve gotten if they were scorers. But here, we’ll honor them by letting you know about three dark horse candidates to win DPOY.

NBA Rumors: Dark Horse Candidates To Win DPOY

3. Jrue Holiday

Several NBA players can all agree that Jrue Holiday is the best defender in the league, yet he rarely gets any love for Defensive Player of the Year. That might change now that Marcus Smart is the reigning winner of the award.

Holiday has long arms and is deadly in passing lanes. He can pick your pocket in the blink of an eye, and his length allows him to haunt rival players all over the court and force turnovers and tough shots.

2. Alex Caruso

Alex Caruso became popular and a fan favorite as a joke, but he earned every single minute of playing time and every penny of his contract. His grit, energy, and hustle make him a major factor for theChicago Bulls.

Caruso is the ultimate ball-hawk. He’ll dive and put his body on the line on every 50/50 balland will hound opposing guards and stick to them like a fly on a frog’s tongue. He’s pesky, suffocating, and physical.

1. Gary Payton II

The Golden State Warriors will regret lowballing Gary Payton II. He was a massive contributor to their recent successand was perhaps the best perimeter defender in the league last season, even ahead of Smart.

Payton II went from an afterthought and barely making the Dubs’ roster to getting a big payday, all thanks to his defense and hustle. Just like his old man, he can even check bigger playersand is strong enough to hold his own in the post.