How Jrue Holiday & Anfernee Simons Trade Impacts Celtics' 2026 NBA Title Odds

It's the end of an era for both Jrue Holiday and the Boston Celtics—and for Anfernee Simons and the Portland Trail Blazers. 

(Photo by Maddie Meyer/Getty Images)

In the early hours of Tuesday morning, ESPN's Shams Charania announced the Boston Celtics were trading veteran guard Jrue Holiday to the Portland Trail Blazers, in exchange for Anfernee Simons and two second-round picks.

A monumental piece of the Celtics 2024 Championship run, the trade was necessary, as the Celtics look to be free from salary cap complications. While it's known the Celtics are expected to move a few stars, Celtics GM and President of Basketball Operations Brad Stevens once showed how masterful Boston's front office is.

Holiday, 36, is set to enter his 17th NBA season after spending the last two with the Boston Celtics. A two-time NBA Champion with the Boston Celtics and Milwaukee Bucks, Holiday is headed to the west coast. It's not the first time Jrue Holiday as been traded to the Portland Trail Blazers. Back in 2023, Holiday was packaged to Portland in a blockbuster deal that sent all-star guard Damian Lillard to the Milwaukee Bucks. Less than one week later, the Trail Blazers flipped Holiday to Boston.

Simons, 26, spent the first seven years of his NBA career in Portland after drafted No.24 overall by the franchise. A viable scoring option, Simons became a cornerstone of the franchise even prior to the Lillards departure.

Let's take a look at the Celtics and Trail Blazers 2025-2026 NBA Championship odds and how the recent trade involving Jrue Holiday and Anfernee Simons affects Boston and Portland. 

Current 2025-2026 FanDuel NBA Championship Betting Odds

Boston Celtics

Pre-trade Odds: +1400 (6.67 % implied probability)
Post-trade Odds: +1600 (5.8 % implied probability)

Bounced by the New York Knicks in the 2025 Eastern Conference Semifinals, the Celtics immediate future is uncertain after star Jayson Tatum suffered a torn achilles in the series.

There's no question Jrue Holiday was a critical piece of the Celtics Championship run, anchoring the Celtics defense in the backcourt alongside Derrick White. Holiday, who has two years left on his $134.4 million contract, is due 32.4 million over the 2025-2026 season. The Celtics lose their defensive pillar, however, Payton Prichard, Simons, and Derrick White are expected to run the Celtics backcourt. That's if White is not moved. Per Charania, the Celtics are expected to be active in trade talks in order to shed salary.

The Celtics odds dropped after Tatum sustained the achilles injury, and had +1440 odds to win the 2026 NBA Title following the Kevin Durant trade. With departure of Holiday, the Celtics gain a prominent scorer in Anfernee Simons.

While it's unclear if Simons will get flipped or become a member of the Celtics—he's set to play on an expiring $27.7 million contract. At 26, Simons is nine years Holiday's junior, and is known as the "microwave scorer" for a reason.

What Anfernee Simons Brings To The Boston Celtics

In 70 games with the Trail Blazers last season, Afernee Simons averaged 19.3 points, 2.7 rebounds and 4.8 assists. Logging 32.7 minutes per game for head coach Chauncey Billups, the guard shot 42.6 percent form the field, and 36.3 percent from beyond the arc. Although Holiday's defensive prowess is unmatched, Simons provides much need scoring ability with Tatum most likely out for the bulk of the 2025-2026 season.

The Celtics odds to win a NBA title drastically dropped even after a 61-21 season. Having finished second in the Eastern Conference last season, I expect these odds to change again. Especially since the Celtics are $18 million over the second apron. As of today, the Celtics starting five would include Derrick White, Simons, Jaylen Brown, and Kristaps Porzingis. Heading into next season, there's much ambiguity given Al Horford, Luke Kornet, and Torrey Craig are all free agents.

With the move saves Boston approximately $ 5 million. However, the Cleveland Cavaliers (+800), New York Knicks (+900) and Orlando Magic (+1200) have all jumped ahead of the Celtics in the Eastern Conference with favorable odds to win the 2026 NBA Title.

While the Celtics next move is unknown ahead of the NBA Draft tomorrow, the Celtics get an offensive upgrade at the point guard position, save in cap space, and receiver a much younger player in Simons.

That's a win in my book for Boston.  

Portland Trail Blazers

Pre-trade Odds: +50000 (.2 % implied probability)
Post-trade Odds: +50000 (.2 % implied probability)

The Portland Trail Blazers once again acquire Jrue Holiday, who will provide an instant boost on the defensive end of things. While the odds haven't shifted despite the trade, there's optimism on the rise in Portland.

The Trail Blazers haven't appeared in the playoffs since the 2021 season, and have been in rebuild mode since the departure of Damian Lillard. Even if Holiday is well past his prime, he brings much needed championship and veteran leadership to Portland. A two-time NBA All-Star, Holiday is a three-team NBA All-Defensive First team, and three-time NBA All-Defensive Second team. Over the course of his NBA Career, Holiday has averaged 15.8 points, 3.2 rebounds, 4.2 assists, and 1.2 steals in 1037 career games. In 2024, Holiday averaged the lowest point total (11.1 PPG) since his rookie season with the Philadelphia 76ers.

Throughout 62 games with the Celtics last year, Holiday additionally averaged 4.3 rebounds, 3.9 assists, and 1.1 steals. In eight playoff games, Holiday put up 9.0 points, 4.1 rebounds, 4.0 assists, and shot 34.6 percent from beyond the arc.

How Jrue Holiday Can Improve The Portland Trail Blazers' Defense

Holiday now joins a Trail Blazers who has a core of Scoot Henderson, Shaedon Sharpe, Deni Avdija, Jerami Grant, and Deandre Ayton. Eliminated with a 36-46 record last season, Portland finished with a 13-14 record post NBA All-Star.

In 26 games post all-star break, Portland emerged as one of the best defensive teams in the NBA. In that span, they ranked No 4 in defensive rating (110.1). While the offense slightly improved from the break, there's a clear defensive identity forming under Billups. There's no better player than Jrue Holiday to reinforce that.

Overall, the trade improves the Trail Blazers, especially on the defensive end. However, the books don't see Portland as top contender. While they are expected to improve from last season, Portland holds the No. 11 overall pick in the 2025 NBA Draft. After selecting former UConn standout Donovan Clingan No. 7 overall in the 2024 NBA Draft, the future is bright in Portland.

The question remains, how does this team stack up against the top teams in the western conference. With the Thunder winning the NBA Title, the Rockets just improved their odds by landing Kevin Durant. As long as Nikola Jokic and LeBron James are in the western conference, I don't see Portland taking down any of those teams. Currently, the Thunder, Rockets, Timberwolves, Lakers, Nuggets, Clippers, Spurs, Warriors, Mavericks, Grizzlies, Pelicans, and Suns are all ahead of Portland in the odds category.