BOSTON, Massachusetts – Brad Stevens, the basketball executive for the Boston Celtics, usually maintains a serious expression, but after observing just one practice with Jrue Holiday on the team, he could not help but smile.
Holiday was shipped to Portland as part of the trade that sent Damian Lillard to Milwaukee, and the Celtics acquired him from there on Sunday. Holiday observed Tuesday’s practice while the agreement was finalized on Sunday, the evening before training camp began.

The following day, Holiday gathered his new colleagues at their practice facility and set the tone that the group is hoping will lead to a title, with Celtics Hall of Famer Paul Pierce watching from the sidelines.

Even though they share the NBA record for most championships (17) with the Los Angeles (and Minneapolis) Lakers, it has been 15 years since the Boston Celtics last hoisted a banner at TD Garden. They have advanced to Game 6 of the NBA Finals twice and have advanced to the Eastern Conference finals five times in the past seven seasons, but they did not appear to be any closer to winning another championship.

Stevens acquired an All-Star big man in Kristaps Porzingis in an offseason shakeup by trading away Marcus Smart, the team’s emotional center, in exchange for Kristaps Porzingis, a point guard and defensive standout.

They feel that they have addressed that in Holiday. With The Holidaymaker joining the All-Stars Jayson Tatum along with Jaylen Brown, Boston became part of Milwaukee, Wisconsin as 19/5 favorites for winning it all, per FanDuel Sportsbook. However, it cost them the services of point guard Malcolm Brogdon, the NBA’s reigning Sixth Man of the Year, forward Robert Williams, and two first-round draft picks.

After beginning his career in Philadelphia and moving to New Orleans for the following seven years, Holiday went to Milwaukee in 2020–21. He teamed up with Giannis Antetokounmpo to win the NBA championship in Milwaukee’s inaugural season. Holiday observed something about the city and its supporters after the Bucks’ Eastern Conference semifinal loss to Boston in seven games the following season.

That also served as a defining quality of Smart’s Boston-based career. The 2022 Defensive Player of the Year, who was a three-time member of the all-defensive team, was well-liked in Boston more for his effort than for his offensive threat from last season, when he averaged 11.5 points and 6.3 assists.

Last season, Holiday matched Smart’s 1.5 steals while averaging 19.3 points, 7.4 assists, and 5.1 rebounds. The fact that Holiday has won the NBA’s teammate of the year award three times, in addition to his two nominations to the All-Star game and his five appearances on the team’s all-defensive team, was specifically mentioned by Grousbeck.

Stevens stated that they will start discussing a contract extension as soon as it is possible even though he is still under contract for two more seasons. By entering into the agreement, Boston went over the new “second apron” of the salary cap, which carries stiffer penalties for clubs with high spending caps.