The Portland Trail Blazers are taking a calculated approach as they navigate what could become one of the most complex rookie scale extensions of the offseason. Shaedon Sharpe, the athletic 22-year-old guard who has rapidly grown into one of Portland’s most promising young stars, is reportedly at the center of “tricky” contract discussions that could push Sharpe's next deal north of $100 million.

Portland’s front office, led by general manager Joe Cronin, has already made its first move. According to multiple reports, the Blazers offered Sharpe a four-year extension in the $90 million range. That number, however, might not be enough to seal the deal as Sharpe’s late-season surge and growing role have boosted his market value. Team strategists across the league believe the Kentucky product could command a contract closer to four years and $100 million or more.

The Trail Blazers must balance future commitments

Portland Trail Blazers guard Shaedon Sharpe (17) attempts a shot over Utah Jazz forward Oscar Tshiebwe (34) in the second half at Delta Center.
Jamie Sabau-Imagn Images
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Sharpe’s development is more than a pleasant surprise for a team trying to return to playoff contention. His breakout second half last season, which saw him average 18.5 points, 4.5 rebounds, and 2.8 assists, gave the Blazers a glimpse of a future cornerstone. Portland views him as a key piece next to Deni Avdija and Toumani Camara, both of whom will be eligible for extensions in the near future. Securing Sharpe now could offer financial clarity before those negotiations begin.

Cronin has expressed optimism about Sharpe’s growth and hinted that Portland remains open-minded about a long-term commitment. The Blazers’ cap space next summer could influence the timing of any deal, allowing flexibility before locking in Sharpe’s number. Still, his performance in training camp has reportedly impressed both coaches and teammates, including veteran guard Jrue Holiday, who praised Sharpe’s “natural scoring instincts.”

Sharpe’s inconsistent three-point shooting remains an area for improvement, but his explosiveness and defensive progress have made him indispensable. For a team aiming to build around its youth, Portland’s willingness to bet big on Sharpe may ultimately define its direction over the next decade.