Boston Celtics weigh cautious buy vs. bold moves as trade season heats up—can Brad Stevens maximize this “toe the line” window without mortgaging future assets? Keith Smith of Spotrac joins John Karalis of Boston Sports Journal to break down the impact of Anfernee Simons’ contract, exploring package scenarios and salary cap strategies to spark roster upgrades. The conversation spotlights Jayson Tatum’s upcoming return, Jaylen Brown’s untouchable status, and how Simons' long-term fit echoes the transformative Derrick White trade from years past.

Key topics include which contracts the Celtics are likely to move, the strategic use of the Kristaps Porziņģis trade exception, and how Boston could become a pivotal third team in multi-team superstar trades this season. Insight on the true value of players like Payton Pritchard and Sam Hauser, plus specific trade targets like Ivica Zubac, rounds out this comprehensive analysis. Don’t miss the inside scoop on Boston’s playoff ambitions and how front office decisions today could shape the team’s future.

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