For Neil Olshey and Clippers, parting was sweet sorrow

PORTLAND, Ore. — For decades, leaving the Clippers was something that could be done with a smile.

Neil Olshey made parting ways with the longtime laughingstock a joyless endeavor.

Particularly for himself.

Olshey fashioned the Clippers into a sail-worthy franchise after eons spent adrift. He orchestrated the most significant trade in team history by acquiring Chris Paul. He also helped assemble a core poised for sustained success, an elusive concept for a franchise that has made the playoffs eight times in its 42-year history.

The Clippers reached the Western Conference semifinals last season for only the second time, setting up even higher expectations among fans who typically dream of .500 finishes.

And then, in the time it took for Paul to lob an alley-oop pass to Blake Griffin, Olshey was gone.

The man who had risen from player development coach to assistant coach to director of player personnel to assistant general manager to director of basketball operations added a new title to his resume: general manager of the Portland Trail Blazers.

“After nine years, I had done everything I felt like I could do there,” Olshey said Wednesday before the Trail Blazers defeated the Lakers at the Rose Garden. “It would have been nice to enjoy the ride for the next period of time with the guys that we had acquired, but it was time for kind of a new challenge.”

The breakup was a bit messy.

The Clippers announced on June 1 that they had reached an agreement in principle to retain Olshey. Three days later, he was on the Trail Blazers’ payroll.

What happened? Portland owner Paul Allen, the billionaire co-founder of Microsoft, swooped in with a contract offer including more money and more years than a proposal previously made by Donald Sterling, his Clippers counterpart.

Call it Deal 2.0.

Olshey’s contract reportedly was for three guaranteed years and $3.6 million, with team options for two additional years. Sterling had offered one year for about $750,000.

Allen “made me a very fair offer in the range that I was looking for with the caveat that if he gave it to me, I gave him my word that I wouldn’t let the Clippers counter,” said Olshey, who had been on a month-to-month contract with his previous employer. “Once I gave Mr. Allen my word, for me it was a fait accompli and I had made a decision to move on.”

Olshey didn’t exactly upgrade in terms of talent.

The Trail Blazers have an All-Star in LaMarcus Aldridge, an emerging talent in Nicolas Batum and a rookie sensation in Damian Lillard. That’s about it, though it was enough to embarrass the Lakers.

Olshey, 47, compares where Portland is in its retooling process to where the Clippers were after the 2010-11 season, when they had the financial resources to re-sign DeAndre Jordan to a four-year, $43-million contract, sign free agent Caron Butler to a three-year, $24-million deal and bring Paul aboard with the hopes of keeping him for the rest of his career.

“I don’t know if we’ll be that lucky here,” Olshey said, referring to the Paul trade, “but we have the same flexibility. And that’s all we’re trying to create, is have a core group of players we’re going to go forward with and then have the [salary] cap flexibility to involve ourselves in player acquisition deals.”

Next summer’s free agent class is a robust one, with Paul, Dwight Howard, Andrew Bynum and Josh Smith potentially in play. And there may not be a better salesman in the NBA than Olshey, a shrewd Mike Dunleavy protege and former soap opera actor on “All My Children” and “One Life to Live” who has a way of making people believe in his vision.

“He did a tremendous job changing the perception of the organization and changing the culture,” one NBA executive said of Olshey’s work with the Clippers, speaking on condition of anonymity because he was not authorized to publicly discuss a competitor. “He made the L.A. Clippers an organization that guys want to play for and that’s no small task considering their history.”

Olshey said the move with the Clippers of which he is most proud was his most scrutinized one, the trade that sent Baron Davis to Cleveland along with a draft pick the Cavaliers eventually used to select Kyrie Irving. The deal freed up the financial resources to solidify the Clippers’ roster and persuade Griffin to sign a maximum five-year contract extension.

Now the Clippers are poised to be contenders in the West for the foreseeable future.

“I watch their games almost as closely as I watch Portland’s,” said Olshey, whose team will play host to the Clippers on Thursday, “because I really have a great affinity for Blake and DeAndre, who I drafted, and Eric Bledsoe, who is in the draft my proudest moment.”

There’s plenty to be pleased about when it comes to the franchise that Olshey put on solid footing before taking a hike some 800 miles north.

“To walk away from it at that point,” he said, “was really hard.”

ben.bolch@latimes.com