Holiday's 2024-25 regular season was a mixed bag. His production dipped in almost all the major categories, and he posted the lowest usage rate (15.8 percent) of his career. He averaged 11.1 points, 4.3 rebounds, 3.9 assists and 1.1 steals over 62 regular-season games for Boston, finishing with ninth-round value on a per-game basis in nine-category formats. A victim of Boston's salary cap crunch, Holiday was traded over the offseason to Portland for Anfernee Simons. Although there was some speculation that Holiday wouldn't want to stick around, that's no longer the case. In Portland, Holiday said he wants to be used all over the floor as he mentors both Scoot Henderson and Shaedon Sharpe. The Trail Blazers also made a massive splash by acquiring Damian Lillard, although he won't return until 2026-27 due to his Achilles injury. It's a pretty safe bet that Holiday will start, but for how long is the question. With the Trail Blazers projected to finish near the bottom of the Western Conference, it would only make sense for Henderson to become the priority down the stretch. But at least in the early going, Holiday has a strong enough fantasy resume over the years to warrant a late-round pick.