Say this about Brad Stevens: He isn’t timid.

Four days after the Milwaukee Bucks swung the pendulum in the Eastern Conference by trading for Damian Lillard, Stevens and the Boston Celtics punched back on Sunday. They re-asserted themselves as a championship favorite by making another big trade.

On the eve of training camp, the day before media day, the Celtics countered the Bucks by scooping up a player who Milwaukee just shipped away. All-Defensive guard Jrue Holiday, the central return of the Lillard trade, is heading to Boston, as the Celtics shook up their core for the second time this offseason under surprising circumstances and made clear how aggressive and serious they are about risking it all in pursuit of a championship.

Anyone ready to just fast forward to an Eastern Conference Finals matchup with the Bucks?

The Celtics, of course, had to part with key members of their roster to swing this deal, but had to do so to beat offers from other contenders and avoid Holiday going to the likes of the Miami Heat or Philadelphia 76ers. Boston has traded Malcolm Brogdon, Robert Williams, a 2024 first-round pick (via Golden State) and a 2029 first-round pick to acquire Holiday from the Portland Trail Blazers.

Before late last week, the Celtics seemed content with their roster. They had made a seismic move in June, trading Marcus Smart in a deal to land Kristaps Porzingis. They were already among the league’s championship favorites. But the Bucks’ move to get Lillard changed their calculations. Specifically, the domino effect that made Holiday available from that trade was too good for Stevens to pass up.

It seemed unlikely, given the significant price Stevens would have to pay to get Holiday, especially since he has only one year remaining of team control. With Holiday set to make more than $36 million, Brogdon’s $22.5 million contract in addition to either Robert Williams or Al Horford was necessary to make the deal. And not only did they deal away Williams – long coveted and valuable, viewed as the key to the Celtics’ run to the NBA Finals in 2022 – but risked their frontcourt depth in the process. In June, Stevens said it was important for the Celtics to balance their roster, which necessitated the Smart for Porzingis swap.

But Holiday changed all of that.

In Holiday, the Celtics effectively have a replacement for Smart and perhaps even an upgrade. Holiday is older at 33 years old, but possesses all the same qualities that Smart had and more. He’s been a nuisance to the Celtics over recent seasons, one of the best defensive guards in the league. He’s a five-time All-Defensive selection, including three on the first team (2018, 2021, 2023). He also gives the Celtics another proven scorer and offensive playmaker. He averaged 19.2 points per game – and shot 38.4 percent from 3-point range – while dishing out 7.4 assists per game last season.

Most importantly, Holiday walks into this Celtics locker room as a proven NBA champion, a key member of the 2021 Bucks alongside Giannis Antetokounmpo. For a Celtics team trying to find a way over the hump, Holiday could be the missing link to help Jayson Tatum and Jaylen Brown find glory.

With the addition of Holiday, the Celtics and Bucks are now co-favorites to win the NBA championship, per DraftKings Sportsbook. The guard helps the Celtics form what could be the most fearsome starting five in the NBA, with Holiday joining Tatum, Brown, Porzingis and Derrick White. The backcourt of Holiday and White – two All-Defensive guards – will be a terror on a nightly basis for opponents.

The deal likely sends Al Horford – who has started every game he’s played with the Celtics – to the bench, where the 37-year-old can stay fresh for another playoff run. The Celtics certainly still have double-big possibilities with Porzingis and Horford, but the loss of Williams – though he has shown to be injury-prone throughout his career – will test the Celtics’ frontcourt depth and rim protection.

Luke Kornet stands to take on an increased load in the regular season, but the Celtics will almost certainly scour the market for a capable big, especially given Porzingis’ health history – he missed the FIBA World Cup this summer due to plantar fasciitis in his right foot – and Horford’s age and durability. The Celtics have a traded player exception worth about $6.2 million they received in the Grant Williams trade that they could use to pick up another big. Could this trade open the door for the return of Blake Griffin, who was a valuable big for the Celtics last season?

The Celtics will now be taking on four significant salaries this season – Tatum, Brown, Porzingis and Holiday will all make north of $28.5 million – and there’s no guarantee that Holiday extends his stay in Boston beyond this year, which makes this move even riskier. ESPN reported that the Celtics will work to sign Holiday to a long-term extension, but they don’t have a lot of salary cap flexibility, already tied to supermax extensions with Tatum and Brown and an extension with Porzingis through 2026. With the second apron looming, is there room for an aging Holiday long-term?

It seems the Celtics are willing to roll the dice.

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