As it tends to happen in the sleepless NBA, the Portland Trail Blazers and Boston Celtics agreed to a momentous trade during Monday’s twilight hours, exporting Anfernee Simons but importing Jrue Holiday and two second-round picks.

Simons, a 26-year-old guard averaging 19.9 points and 4.5 assists per game over the past four seasons, now fulfills his heart’s deepest desire. Holiday, for the third time in his career, finds himself on a team looking to turn their franchise around.

Unlike the first time he was in the City of Roses, Holiday won’t be re-routed elsewhere. For posterity, the Blazers are the team that sent him to the Celtics in the first place, prioritizing the development of their young backcourt. However, “the plan is to keep” Holiday this go-around, according to The Rose Garden report’s Sean Highkin.

Such a decision signals a serious change in Portland’s direction. Since trading Damian Lillard, arguably the top player in franchise history, they’ve been in a rebuild. Over the past two seasons, they’ve won just 57 games, ranking in the bottom fifth of the West. Though it hasn’t been pretty, it’s been fruitful with regard to certain players’ evolutions.

After a rough rookie season, 2023 No. 3 pick Scoot Henderson made real progress in sophomore campaign. Though he was still up and down, he was more efficient and less erratic. In his 10 games as a starter, he averaged 16.2 points, 6.5 assists and 1.1 steals per game while shooting 47.5 percent from the field and 43.6 percent from 3.

Last season, Blazers wing Shaedon Sharpe averaged a career-high 18.5 points per game on 45.2 percent shooting from the field. Portland is enthralled by the 22-year-old Canadian. He needs to clean up his defense and long-distance shooting but has natural guard skills and prototypical physical attributes for his position.

Though he doesn’t play in the backcourt, Deni Avdija displayed star potential after the 2025 All-Star Break. In 20 games, the 24-year-old combo forward averaged 23.3 points, 9.7 rebounds, and 5.2 assists per game. He was deadly from 3-point range, knocking down 41.7 percent of those attempts.

Holiday joins this perimeter group providing not just his experience as a two-time NBA champion and two-time NBA All-Star but defensive expertise, 3-point efficiency and playmaking.

With regard to their defense, Portland’s certainly not the worst.

Yet, their defensive rating has been in the bottom-half of the NBA the past two seasons. This is despite having three of the league’s better defensive centers (Deandre Ayton, Robert Williams III and Donovan Clingan) on the backline. Not to be forgotten is second-year forward Toumani Camara, who earned a 2024-25 All-Defensive team selection.

Given that, improving their point-of-attack defense has been an emphasis, with Simons and Sharpe’s performances at that end considered weak links. This an area where Holiday can help, unless Father Time has something to say about it.

With that being said, his age (35) generates some concern. Nevertheless, the 16-year veteran’s one of the league’s most battle-tested players. More to the point, his basketball IQ will also come in handy at the defensive end, from teaching technique to calling out plays.