Should Blazers give in to Damian Lillard’s monstrous contract demands?

Damian Lillard wants to be paid substantially to stay with the Portland Trail Blazers, a move that will force Portland to return their loyalty to Lillard.

Damian Lillard denied reports earlier this week that he isn’t happy in Portland, but his recent contract expectations show that Lillard wants to be paid what he believes he is worth.

According to ESPN’s Adrian Wojnarowski, Lillard wants a two-year, $107 million extension that would be added to the end of his current four-year contract. If signed, the extension would keep Lillard in Portland for the next six years for nearly $300 million, solidifying his commitment to Portland.

The question is, will the Trail Blazers return Lillard’s longstanding loyalty to the team?

Trail Blazers facing consequential decision on future of Damian Lillard

As integral as Lillard is, his asking price of a two-year extension for $107 million is rather steep, even for the Trail Blazers point guard. Lillard is already on a four-year, $176 million contract that began this season, meaning his contract extension wouldn’t take effect until 2025. If the Trail Blazers agree, they’ll still be paying Lillard $55 million when he is 36 years old.

Clearly, Lillard wants Portland to commit to him after he’s committed his entire ten-year career to the Trail Blazers. A 2013 Rookie of the Year, a six-time NBA All-Star and one of 75 basketball legends on the exclusive NBA 75 team, Lillard remains without a ring during his time in Portland.

As evidenced by the recent firing of general manager Neil Olshey, the Trail Blazers organization is ride with mismanagement and turnover, which miraculously has not caused Lillard to leave for a better situation.

Should the Trail Blazers pay Lillard? It’s a lot of money, but to continue getting the best years out of Damian Lillard, it’s something that Portland should seriously consider.

Even though the salary cap is set at $112 million for the 2021-22 season, the NBA will be renewing its collective bargaining agreement (CBA) following the 2023-24 season. When new CBA agreements are drafted, players often position themselves for expanding the salary cap, while owners could argue for major television deals. If the NBA follows the NFL’s trend, the salary cap will expand in coming years with new television and sports betting deals being inked.

Even though $55 million a year is $10 million more than Steph Curry is making with the highest annual average salary, those prices will likely jump in the next four years. By that point, the Trail Blazers may be able to build a championship-worthy roster by Lillard’s extension — and they’ll need Lillard to pull it off.