Shaedon Sharpe is the one Portland Trail Blazers player whose upside you want to bet on most. Fortunately, Portland did just that, inking him to a four-year, $90 million extension prior to the season.
Some think the decision came with risk attached, given his relative lack of impact on winning the past three seasons, but we're not buying it. At worst, Sharpe can be valuable in a sixth-man role on a contender.
Few guards in the league can compete with his rare combination of physical tools and skill set as a guard who has to worry about hitting his head on the rim while also somehow looking like the smoothest player on the court with the ball in his hands.