Boston Celtics eye a strategic offseason with Anfernee Simons as a potential long-term sixth man. Could a championship run fuel Simons’ breakout and redefine his market value? John Karalis and Keith Smith dissect the Celtics’ options around the NBA trade deadline and beyond, debating whether to keep Simons using Bird rights at a team-friendly deal. They evaluate Simons’ evolving role behind stars Jayson Tatum and Jaylen Brown, his fit next to Payton Pritchard and Derrick White, and how second apron restrictions limit rival bidders. The conversation includes Simons’ locker room mindset, the impact of Joe Mazzulla’s coaching, and what embracing a Lou Williams/Jamal Crawford-style career could mean for Simons and Boston. Can Brad Stevens’ front office build a roster that maximizes Simons’ talents and keeps the Celtics at the top of the Eastern Conference? Tune in for expert salary cap analysis and insights on Boston’s championship blueprint.