Portland Trail Blazers: Will Damian Lillard Ever Win In Rip City?

Dec 20, 2016; Sacramento, CA, USA; Portland Trail Blazers guard Damian Lillard (0) during a game against the Sacramento Kings during the fourth quarter at Golden 1 Center. The Kings defeated the Blazers 126-121. Mandatory Credit: Sergio Estrada-USA TODAY Sports
Dec 20, 2016; Sacramento, CA, USA; Portland Trail Blazers guard Damian Lillard (0) during a game against the Sacramento Kings during the fourth quarter at Golden 1 Center. The Kings defeated the Blazers 126-121. Mandatory Credit: Sergio Estrada-USA TODAY Sports /

Will Damian Lillard ever win with the Portland Trail Blazers?

A question that fans ask and athletes continue to ask…when is enough simply enough? Veteran guys come to a point in their career when the reality of retirement becomes inevitable, organizations debate the futures of tenured coaches for fresh faces, and stars often seek services elsewhere when goals are not met.

It’s over before you know it, your favorite guy is the epitome of the league and when you blink he’s begging to make a comeback ( Cough, cough Baron Davis).

As of late, key players in the league have started to follow the trends of the guys before them when approaching free agency.

It started with Ray Allen and Kevin Garnett assembling in Boston with Paul Pierce to form “The Big Three,” that would then transcended to what NBA stars are doing with their free agency today. With LeBron James, we all remember, “The Decision,” the hoopla/hate that followed immediately after and how after seven years in Cleveland, King James decided to take his talents to South Beach to finally win a Championship.

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The “super team” bravado was established and later to follow suit in 2016 Kevin Durant would leave the blue-collar confines of Oklahoma City to join the boys in Oakland named Curry, Green, and Thompson.

Fast forward to the 2016-17 season and Damian Lillard may find himself in the same boat come three years from now. With Lillard approaching unrestricted free agency post 2020-21 season, should he be looking for real estate elsewhere?

Headlining the positives for the future of Dame starts first and foremost with C.J. McCollum. McCollum was locked up for the next four years in the 2016 offseason after the Trail Blazers signed the 2nd-year starter to a four-year contract extension at the max worth $106 million. McCollum is Robin to Dame’s Batman and maybe it’s vice versa, but for the time being it is working.

McCollum shoots above 45 percent from the field and has upped his effective FG percentage and PER (Player Efficiency Rating) over the last two seasons. The only concern is if he and Lillard can effectively share possessions as time goes on and keep others involved. While Lillard needs the ball in his hands a la Derek Rose early in his career, McCollum can operate without it, but still needs X amount of possessions for the offense to prosper.

Other concerns surround the mentality of this team, exactly who are the Portland Trail Blazers? This is a flaw repeatedly noticed in Head Coach Terry Stott’s team’s year after year, especially come postseason time – he’s never been past the second round in the playoffs.

Is Portland the up and down team we have seen in spurts? Will they operate in the hi-lo using their talented, but young big men, to space the floor while letting Lillard and McCollum move without the ball? Does the offense feature a competent third role player to score buckets on the off nights that “Dame Dolla” and his sidekick can’t get it going?

Can Stotts take Lillard to the next level?

Those not named Lillard or McCollum who average more than 15 MPG ( Minutes Per Game) are totaling 49 plus points per game while the duo is averaging near 50 points per contest according to basketball reference dot com.

On every championship team, there’s a whole lot of talent, but also present is coaching that must go along with that talent in order to be efficient. Is Head Coach Stotts the man for the job when you think of Portland actually contending to beat the Golden State Warriors? Do you think of Stotts when thinking of the next coach to lead his team to an NBA title?

Can Stotts take Lillard to the next level? Although Lillard may be an exceptional player, is he making the guys around him better?

Stotts, who is in his fifth year with the Portland Trail Blazers, has a career win percentage of 48 percent and has never made it past the second round in the playoffs while arguable vying for Coach of the Year in the Western Conference on two occasions. The general sentiment is that Stotts is safe despite the team’s early troubles with a returning roster from 2015-16. Stotts just signed an extension in 2016, but when will enough be enough for the front office if it seems that the Trail Blazers have plateaued.

The Western Conference is only getting better and with teams like Houston finding their stride, along with the youth emergence in Los Angeles and Minnesota, Lillard’s time along with Stotts will continue to race against the clock.

If Stotts should come up short this season (which is highly likely) and again post 2018, a change at the helm might be on the table. While the Portland Trail Blazers moving forward might not be out the picture, starting fresh with a new coach won’t go over well for a player approaching 30 years of age entering his prime.

If Damian Lillard should decide to take his talents elsewhere, a reasonable destination would be the Eastern Conference. A pairing with Jimmy Butler in Chicago, teaming up with Paul George in Indiana, or possibly landing in the garden with Kristaps Porzingis would be favorable landing spots for a PG of Lillard’s stature.

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This could very well be a damning overreaction to the ups-and-downs in Portland, but Damian Lillard doesn’t want to end up like the stars in the commercials he costars with and no ring to show for. His time is now, along with the planning of his future.