Does Damian Lillard Deserve to Become the NBA's Highest-Paid Player?

Damian Lillard's name has been in the news often this week despite his absence from the court of play with an abdominal injury he's apparently been dealing with for years. Yesterday, reports (that Lillard quickly shot down) suggested the superstar point guard wants the Portland Trail Blazers to shake up the roster and maybe even go so far as to adding Ben Simmons. Today, Adrian Wojnarowski reports the Blazers' search for a new GM may be complicated by Lillard's desire to sign a two-year supermax extension this offseason.

Such an extension would pay Lillard over $50 million per year (!!!) into his age-36 season. Therefore the organization and whoever they hire to make this decision for them are faced with a pivotal choice: does Lillard deserve that money?

The obvious answer is no. These kind of big-money extensions have only recently entered the NBA zeitgeist in the last CBA but not a single one has looked good in retrospect for players in their 30s. Chris Paul is the only one you can make an argument for, given his production while making around $40 million a year before he restructured and signed an extension with the Suns. But until he ended up in Phoenix his contract was considered among the most untradeable in the NBA. He was sent off by three different teams over its lifespan. Russell Westbrook's supermax looks heinous and the fact that he was also traded twice is a borderline miracle.

There are just very few players who are worth $50 million a year. The only teams that can afford to pay that kind of money are the ones who know they have a legit No. 1 option on a chamionship team. There are exactly four players who can justify making that kind of money: Stephen Curry, LeBron James, Kevin Durant, and Giannis Antetokounmpo.

Curry is probably the closest comparison to Lillard as an aging point guard, but he is a generational talent who has already won multiple championships, one as the top option. Lillard is a superstar in his own right but isn't anywhere near Curry's level, which is OK because very few players in league history have ever been.

But that is the problem the Blazers face: Lillard wants to be paid like Curry without the accolades or proof of championship contention that come with that. Worse, he currently has a lingering injury problem that has been going on for years and certainly will not get better as he gets older. Paying $50 million to one player, no matter what his teammates are making, ensures it is nearly impossible to reconfigure the roster around that player. Unless the cap skyrockets in the near future in the same way it did after the 2015-16 season, it is not feasible to do anything with a roster that features one player making nearly a quarter of the cap.

Here is the one argument for giving Lillard that money: it keeps the best and most beloved player in franchise history happy. That puts butts in seats. That ensures the Allen family remains profitable in one of their two professional sports enterprises. Even if the Blazers live in the basement until Lillard retires, Blazers fans will show up in droves to cheer him on. It's somewhat similar to why the Warriors gave Curry that money (with the obvious differences noted above): Curry is The Guy in the Bay. No matter what. Sometimes, paying that guy more than what he is technically worth on a spreadsheet is worth it.

What decision the Blazers make will indicate where they fall on that particular opinion. It's a very tough sell to a potential GM if they want to give Lillard that money. They're setting up the new front office to fail in that regard. But if they don't give Lillard that money, they indicate to both player and league that change could be coming. That won't sit well in the court of Blazers' public opinion, even if it's the smart move.

It is a tough balance to strike. Usually such problems are good ones to have. Not this time. Portland has a painful call to make.