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Even though Damian Lillard has said time and time again that he will remain in Portland, the media isn’t going to stop bringing up if Lillard should leave and join up with other stars.

After another disappointing loss in last year’s playoffs to an undermanned Denver team, Lillard was pretty honest when he said things needed to change in order for the team to contend.

“We didn’t win a championship, so obviously where we are now isn’t good enough. I don’t know what a shakeup looks like or what changes will be made or could be made, but obviously as is, it wasn’t good enough. Obviously, where we are isn’t good enough to win a championship if it’s not good enough to get out of a first-round series with two of their best three or four players not on the floor.”

The Blazers front office definitely felt pressure after, as long-time head coach Terry Stotts was let go. However, the team did not make any major moves to shake up the roster, so naturally the media is breathing down their necks.

Legend Shaquille O’Neal was recently on the Rich Eisen Show, praised Lillard for wanting to stay with his franchise and appreciating his kindred spirit as someone with an old-fashioned mindset.

“He is an old school mentality guy that’s playing in the new school. The old-school guy would say, ‘I’m not teaming up with you, I’m gonna beat you’. But these new school guys would say, ‘hey, let’s team up to make it easier.’ So that’s the toughest decision for him.

O’Neal also mentioned that it may be time for Lillard to leave and team up with other stars if he was serious about winning.

“I know he wants to stay in Portland and win it out, but he may have to switch up his mentality. If everybody else is doing it, then that’s just gonna keep him further from winning a championship. I don’t really like guys teaming up, but it’s just the way it is these days. If he can get to a team that already has two or three guys, and you add him? That raises his chances of winning a championship.”

O’Neal isn’t wrong here, as one needs to adapt to contend with peers in order to stay relevant. The league is different now, and stars team up together in order to contend for titles. Lillard staying in Portland is for sure commendable, but if he’s serious about winning titles, he may have to look to team up with other superstars. History has shown that superstars normally don’t ask to play in Portland. Like any other field, when the efficiency improves or technology advances, one must keep up and adapt in order to remain as an effective worker in ones respective industry.