“Damian Lillard is completely content in being a very big fish in a pretty small pond” - Skip Bayless says he can’t condemn Dame for staying put and milking the NBA system for all it’s worth

In an era in which star NBA players are on the move, Damian Lillard is an outlier. While the Portland Trail Blazers have struggled to contend in the Western Conference, the All-Star point guard has remained loyal to the franchise that drafted him in 2012.

From the beginning, Lillard has refused to jump ship to form a super team. He wants to win, but in Portland, where his NBA journey began.

Even after a season when the Blazers shipped out multiple key pieces, Lillard is committed to the future of the franchise. Despite having three years remaining on his current contract, he recently signed a two-year, $121.7 million extension keeping him in Portland until at least 2027.

While many have mixed feelings about Dame being so adamant in regards to staying in Portland, one analyst feels he shouldn't be criticized. On FS1's "Skip and Shannon: Undisputed," Skip Bayless applauded Dame for taking advantage of the NBA's system when it comes to contracts.

"I just believe Damian Lillard is completely content being a very big fish in a pretty small pond," Bayless said. "I can't even begin to criticize him for staying put and milking this NBA system for all it's worth. He is, as we speak, on pace to become the third-highest paid player in the history of the National Basketball Association."

Will Damian Lillard ever request a trade from the Portland Trail Blazers?

2022 NBA Summer League: Portland Trail Blazers guard Damian Lillard

The "Damian Lillard sweepstakes" are something that NBA fans have talked about for years now. Things seemed to be heading in that direction last summer, but in the end, he opted to remain with the Blazers. While Lillard should be applauded for being loyal in an era full of star trades, the question has to be asked if he will ever have a change of heart?

At 32 years old, Dame is on the back end of his prime. With only a limited number of years left at his peak, the window to lead Portland to a title is small and closing more rapidly. Securing a championship is something every player dreams of doing and could be the deciding factor in Lillard staying loyal to his franchise.

Legacies are something brought up constantly when talking about star players, and rings are always the first thing mentioned. If Dame wants to go down as one of the best of his era, he will need to win on the biggest stage. Given the current outlook of the Blazers, his timeline doesn't match the rest of the group.

Dame has done everything he could for the Blazers over the years and is on track to be the most loyal superstar of the player empowerment era.