Damian Lillard: 4 years, $196 million (Portland Trail Blazers)
On the one hand, smaller markets have to hang onto their superstars when they can. Damian Lillard’s loyalty to the Portland Trail Blazers has been well-documented, and the team is coming off a feel-good trip to the Western Conference Finals, but more playoff exits usually result in unrest for the game’s biggest stars.
That’s why this four-year, $196 million supermax extension, which will pay Dame $54.3 million in 2024-25, was a necessary evil. Watching Lillard outplay Russell Westbrook this season (and in their head-to-head playoff series) put the four-time All-Star in rarified air among the league’s elite crop of current point guards.
However, even with a rising salary cap, this gargantuan extension severely clogs up Rip City’s books for the next six years, which will in turn make it harder to put a championship-caliber roster around one of the greatest players in franchise history. Making sure Dame is a Blazer for life is priority No. 1, but every move from here needs to be made with care in order to properly construct a winning team. The margin for error is razor-thin now.