July 2, 2010 was a bright Friday in Cleveland. Early that afternoon, Los Angeles Clippers vice president of operations Neil Olshey and team president Andy Roeser arrived at the headquarters of LRMR, the marketing firm owned by LeBron James and Maverick Carter.
The Clippers, set to pitch themselves as the best match for James' talents, were being ridiculed like an eccentric presidential candidate on a quixotic campaign. They didn't seriously think an athlete as brand-conscious as James would suit up for them, did they?
Olshey had heard the snickers from around the league and the web. Privately, he was well aware that, next to the Cleveland Cavaliers, Chicago Bulls, New York Knicks, New Jersey Nets and Miami Heat, the Clippers were the paupers at the garden party. Basketball luminary Sonny Vaccaro had helped Olshey broker the meeting as a favor, and Olshey's expectations that James would be his starting small forward in 2010-11 were modest.
"We were on an audition and everyone else was on a callback," Olshey said. "The other teams that were in there were already further down the road with [James] than we were. We were trying to play comeback ball."
The Clippers took a minimalist approach with their presentation. Olshey couldn't brandish any championship rings, and he wasn't flanked by a hip-hop icon. There were no PowerPoints diagraming how becoming a Clipper would make James a billionaire, or rosy testimonials about the franchise's storied history.
While five other teams had their sights set on landing James, Olshey was engaged in a far broader mission, one that mirrored his improbable journey to that office tower on the banks of Lake Erie.
The early days
Olshey grew up in Flushing, Queens (N.Y.), where he had aspirations to play basketball at Xavier High School in Manhattan, but the cruel realities of verticality dictated otherwise.
"The freshman coach did exactly what I would've, but at that point broke my heart," Olshey said. "I was 5-feet-something, and there was a kid 6-foot-5. One of them was going to make the team, and the other one wasn't. And they went with the 6-foot-5 guy."
There is no shortage of outlets for a New York kid who needs to feed his obsession for basketball. Olshey played Catholic Youth Organization (CYO) ball, high school summer league, AAU and on any city court where he could find a game.
In 1983, he went to Le Moyne College in Syracuse, N.Y. Olshey was tapped for the lacrosse team, but played intramural basketball and pickup games in the gym whenever he could. When Le Moyne coach John Beilein, now the head coach at Michigan, was a few bodies short for a 5-on-5, he'd grab Olshey and throw him into a 2-3 zone.
After graduating, Olshey spent a couple of years working in advertising in upstate New York before landing back into the city. He had friends in the acting world who encouraged him to have headshots developed and to take a meeting or two with talent agencies. He enrolled at the prestigious Neighborhood Playhouse School of the Theatre, which had produced Robert Duvall and Diane Keaton, among other high-profile actors. The feedback was good, and Olshey had a few cups of coffee in the New York acting scene, including some small TV roles.
While other young actors spent their Friday nights clubbing, Olshey would check out the big Catholic League high school games -- New York City's equivalent of high school football in Texas. If Christ the King were playing Archbishop Malloy, it's a safe bet Olshey was in the stands watching Kenny Anderson light up the court.
In the spring of 1993, Olshey moved to Los Angeles, where he had some initial success acting in national commercials for brands like Honda and Coca-Cola. Commercial shoots aren't the most artistically fulfilling roles, but they pay well and afford working actors the luxury of free time. This was fortunate, because Olshey was suffering from an acute case of basketball withdrawal.
Laying the foundation
Olshey could navigate the New York basketball world without a map, but knew virtually nobody on the Southern California landscape. After working his personal network, he was invited to join the staff as an assistant at Artesia High School, one of the region's powerhouses. When he got there, Olshey realized he needed to find a skill that he could cultivate as his calling card.
"In order to find a niche on the staff, I jumped into player development," Olshey said. "We've got like five assistants, but this is where I can make an impact and relate to the players and really get something out of these trips every day as opposed to just sitting on the bench with a clipboard."
Coaching at Artesia stoked a passion that was far more exhilarating than anything he experienced on a commercial shoot. During Olshey's second season at Artesia, he worked closely with an incoming student named Jason Kapono, with whom he built a close player-coach bond, a friendship that still exists today. Artestia's gym was also the site for NBA assistant coach Tim Grgurich's summer workouts, which have always attracted a slew of NBA players and assistant coaches. Olshey happily shagged balls, set screens and chased guys off picks for Grgurich.
Serendipity was definitely at work for Olshey. Who knew that volunteering to help out with a high school team would eventually allow him to brush shoulders with Gary Payton, Shawn Kemp and a legion of NBA assistants? But Olshey's time at Artesia demonstrated his strategic instincts. He grasped early on that player development was something that was lacking at all levels of coaching. He understood that being in the good graces of Grgurich was a smart place to be. And by paying close attention, he learned what kind of cues talented players responded to.
Olshey eventually established his own player development business in Santa Monica, Calif. He consulted for a few agents, working out their prospects in preparation for the draft, and picked up a few local high school kids looking to refine their games.
"I really enjoyed being on the court with guys, interacting with players, watching them get better," Olshey said. "I had a core group of 10 to 12 guys at all different levels and that was the business."
When Kapono chose UCLA, he asked Olshey to work him out the summer before his freshman year on campus. When word got out that Olshey was doing solid work with Kapono, local players who weren't eligible to practice with their current or future college coaches during the offseason began to flock to the gym to work with Olshey.
"[Olshey] is an engaging, social, generous person," Kapono said. "He'd work me out on Sunday mornings at 8, and I always got there [at] 8:20, 8:30, 8:40. You'd think that at some point he'd get pissed off and say, 'If you're not going to be here on time, I'm not going to show up at the gym at 8 a.m. on a Sunday morning.' But [Olshey] never did that."
Agent Arn Tellem, who represented Kapono for the draft and was close to Grgurich, hired Olshey to run a pre-draft camp for his agency, SFX, at Saint Monica High School. The camp was a new twist on an old concept. Tellem realized that agencies held the commodity -- hot young prospects. That being the case, why should NBA teams control the pre-draft workouts? Why not tell team execs that if they want to see those players in action, they should come to Santa Monica, where they could observe the firm's clients? That's when Tellem called upon Olshey.
"We were very impressed with Neil," Tellem said. "He had an incredible work ethic and a great ability to communicate with players, engage with them and connect with them. He didn't go through the motions. While he was a gym rat and loved the technical aspects of basketball, in one conversation with him you knew he had a much deeper knowledge of the business."
SFX was able to lure top basketball operations people from virtually every NBA team to Santa Monica for the agency's showcase of talent -- and Olshey was the guy running the show. The workouts were meticulously organized, which execs liked and reflected well on Olshey. Because SFX controlled the workouts, Olshey was able put SFX's young clients in the best position to succeed.
"A GM's job is to find holes in a player's game," Olshey said. "My job was to cover up those holes. Now, we went live. It wasn't a beauty pageant. It was all the same stuff they would do [for an NBA team's workout], but I wasn't going to have Gerald Wallace spot-shooting 50 3s. I was going to have Gerald Wallace slashing, catching lobs, attacking and playing one-on-one defense."
A few weeks later, the 2001 draft could have hardly gone better for SFX. Kwame Brown went No. 1. Eddy Curry, Eddie Griffin, Joe Johnson, Kedrick Brown and Vladimir Radmanovic were all chosen in the lottery. Jason Collins and Wallace were also first-rounders. Olshey had a big hand in that success but, more importantly, he had organized some of the best draft workouts NBA executives and coaches had ever seen.
The big break
During his tenure with SFX, Olshey's biggest break came when he was invited in 2001 to serve as a coach at Vaccaro's ABCD Camp, a summer gathering of the best young high school players in the nation. ABCD Camp was one of the basketball world's tent-pole events, and it was unheard of for someone who wasn't affiliated with an NBA team in a front office or coaching capacity to work the camp, but Grgurich vouched for Olshey.
"ABCD Camp put me in the mix with all these NBA coaches and front-office guys in an environment I was comfortable in, so that it demystified the 'How do I hire a guy who didn't play in the league?'" Olshey said. "The other part of it was the value from an intel standpoint. When you have to have conversations about Dwight Howard or Shaun Livingston or all the guys in a draft class, you knew them from ABCD camp and from sitting with Sonny in gyms, and getting to know their AAU coaches, and getting to know the kids, eating with them in the dining hall, getting to know their families and learning what kind of people they were. That experience bears fruit."
As Olshey was explaining all this, Clippers guard Randy Foye passed by on his way to Staples Center court for warm-ups.
"Here's one of them now," Olshey said to Foye. "We were just talking ABCD Camp."
Foye smiled. "That was me, Allan Ray -- "
"Curt [Sumpter]?" Olshey asked.
"Curt and Jason Fraser!" Foye said.
As Foye trotted out of the corridor, Olshey remarked how life came full circle. Foye was a counselor at ABCD camp while Olshey was a coach. A decade later, Olshey signed Foye to a two-year free-agent deal when he needed a guard to back up Eric Gordon.
Olshey called it the place "where I made my bones." It's one thing to have your own gym with your own clients or clients provided by an agency you're consulting; it's quite another to work with top NBA assistants and execs, 200 of the best high schoolers in the country and 75 college standouts who are working as counselors alongside you.
"He worked these kids when they were kids and he got to know them," Vaccaro said. "He has this special ability to communicate and motivate."
Olshey never lacked for confidence -- one team executive recently described him as a guy who walks around with his chest puffed out -- but Olshey also knew he had an unconventional résumé in a business that placed a premium on pedigree. But ABCD Camp was an equalizer.
"At ABCD Camp, we all started on an even playing field," Olshey said. "All those high school kids? All they want to know is are you making them better? They didn't care if you had a Spurs shirt on or a Clippers shirt or an adidas shirt. If you knew what you were doing and you were helping them get better, that's what mattered to them."
Olshey had identified yet another situation in which he could use his affability and expertise to build trust with some of the most powerful people in basketball.
At home with the Clippers
When Mike Dunleavy Sr. was hired by the Clippers in 2003, he watched Olshey orchestrate workouts in Santa Monica and was impressed.
"I thought he handled things the right way," Dunleavy said. "As far as the paces he put them through, things he asked them to do, the way he communicated -- it was very positive. I felt he could translate that on an everyday basis to NBA players."
Olshey came aboard as the team's director of player development for the 2003-04 season. After acclimating to life inside an NBA organization, he gradually cultivated a rapport with Dunleavy, who asked that his new charge sit next to him on team flights.
"I knew Neil wanted to learn more and maybe be a coach, so we'd go through the whole process," Dunleavy said.
For all his time in the gym, Olshey arrived to the Clippers without a firm grasp of NBA-level X's and O's. A lot of assistant coaches and personnel people get by on their work ethic, bedside manner and bloodlines to the game. But Olshey wanted to master the nuances.
"Two years of Mike [Dunleavy], embracing me, giving me the opportunity to work with him on the offense -- it forced me to do more," Olshey said. "It was phenomenal for me. I still look at the game through his eyes a little bit."
In exchange, Olshey was able to provide Dunleavy with some scouting for upcoming games. Olshey knew the guards least equipped to handle Elton Brand on a mismatch, and which opposing big men the Clippers could abuse in a pick-and-roll game. Pretty soon, Olshey started to work up game plans, and his role on the staff grew.
Dunleavy elevated Olshey to assistant coach for the 2004-05 season, but both men arrived at a realization -- Olshey's true calling was in player personnel. He was fluent in an entire generation of players, and understood the life cycle of a prospect, from AAU ball to the NBA.
"I really felt like the trajectory as a career path that I had a better chance of becoming an executive in a front office than a head coach," he said.
Having surveyed the field, Olshey recognized that the line was shorter in management for someone with his biography. He made the pivot, then quickly studied up on the NBA salary cap, reached out to agents who might have still known him only as a "workout guy," and forged a tight working relationship with Roeser, who functioned as the intermediary between Clippers ownership and management.
The secret behind the LeBron meeting
As the Clippers' season cratered in early 2010, Dunleavy was relieved of his role as head coach in February, and then was fired as general manager one month later. Enter Olshey, as Dunleavy's interim replacement.
"Mike guided me through the process," Olshey said. "I hate that it was a battlefield promotion."
As much esteem as Olshey had for Dunleavy, he was in a perfect position to fill the vacuum left by Dunleavy's departure and, true to his nature, he had a plan for shedding the "interim" tag and making himself indispensable to the organization.
Before Dunleavy's firing, he and Olshey worked quickly to free up cap space for the summer of 2010, moving Marcus Camby and Al Thornton for a collection of expiring contracts. In 2010, Olshey selected Al-Farouq Aminu at No. 8, then dislodged Eric Bledsoe from the Oklahoma City Thunder later in the first round in exchange for a first-round draft choice.
A couple of weeks later, Olshey and Roeser were sitting with James and Carter in Cleveland.
When you accept a job with the Clippers as the vice president of basketball operations (a position many organizations call "general manager"), you're not just moving the pieces on the chess board; you're engaging in a rebranding exercise. The Clippers' historic futility has been well-chronicled, and Olshey balanced his awareness of it with a steadfast belief that the franchise's stigma could be tempered with smart management.
For Olshey, altering the league's collective opinion of the organization was the most important item on his to-do list, and the Cleveland trip was the opening act of that project. The meeting with James was vital to Olshey's long-term plan to change the way the top power brokers in basketball regarded the Clippers, particularly those at Creative Artists Agency, who had become extremely powerful in recent years as they've stockpiled many of the NBA's shiniest stars.
"What it accomplished from an education and relationship standpoint was to accelerate the learning curve for CAA about our organization and where we were trying to go," Olshey said.
"You kind of have to educate the marketplace a little bit about how we're not the Clippers and whatever perception you might have of the organization: 'The reality is this. These are the guys we've paid. These are the draft picks we've moved. These are the resources we have. This is the practice facility. This is our cap flexibility.'
"So what it did was it basically gave us an hour-and-a-half and the beginnings of a relationship with (agent) Leon Rose and CAA."
Olshey knew that the road to acquiring top talent in the NBA would go through CAA for the foreseeable future. CAA is a savvy, full-service agency that steers its clients to the most desirable employers. When it comes to its most marketable stars, CAA is not inclined to futz around with a franchise if it perceives that a player can't maximize his opportunity for success there. Olshey regarded getting the Clippers off the bad list and on the good list as vital to the health of the franchise, and that could happen only by being proactive.
"Do you really think that prior to Neil Olshey the Clippers would've had the balls to ask for an audience with LeBron James?" Vaccaro said. "Didn't that show the world something right there? We all knew [James] wasn't going there, but Neil did all he could, pulled all the puppet strings and he got the interview."
That was the signal Olshey wanted to transmit to players and agents, particularly Rose and his stable of stars: The Clippers could handle themselves at the NBA's adult table. Olshey wasn't a denialist. He knew the history of the franchise and, more important, he knew that you knew that he knew. But he felt deeply that there were assets to be pitched.
"[The meeting with James] was one of the first substantive interactions," Rose said. "The process helped the Clippers and they represented themselves well."
The Clippers had acquitted themselves fairly well and were developing an intriguing core of young players. Olshey was still getting his feet wet, but he felt confident that, if the Clippers continued to play the long game, they might receive an incoming call the next time a superstar went shopping for a team.
Preparing for the future
Around much of the league, there were doubts that Olshey would be around to execute his long-term plan. He was hired on an interim basis, and the Clippers had underperformed somewhat in the 2010 free-agency market. Well into that summer, he was still listed as assistant general manager in the team's directory. The Clippers could probably attract a name executive if they wanted to, so why wouldn't they shop the marketplace? Olshey himself was aware of this perception.
"If I was a guy who had played in the league for 15 years and was an All-Star, or I had been a general manager, I would think, 'Why would they hire this guy?'" Olshey said.
The organization decided to stay with Olshey. During the 2010-11 season, the Clippers came out of the gate 1-13, but they split their last 20 games. More important, Blake Griffin, the team's No. 1 pick in 2009, emerged as a bona fide star, a supernova for the social media age. Olshey could sell that along with a young core that was starting to grow up. He still had a tradable asset in Chris Kaman -- and a less tradable one in Baron Davis.
Sources claim that Olshey had sculpted at least one trade for Davis during the previous offseason, but the deal was scuttled by owner Donald T. Sterling. At the trade deadline in February 2011, Olshey finally pushed a deal through, sending Davis (and his hefty contract) and an unprotected 2011 draft pick to Cleveland in exchange for Mo Williams (shorter contract) and Jamario Moon.
Overall, the Clippers saved over $12 million in the deal. Although the pick had only a 2.8 percent chance of landing No. 1, it defied probability. Olshey and the Clippers had to suffer that indignity, with many howling that Olshey had made a colossal mistake by not protecting the pick. The Stepien Rule, which dictates that a team can't trade first-round picks if it could be left without one in consecutive years, prohibited the Clippers from protecting the pick, which had only a 1-in-36 chance of landing at No. 1.
With more flexibility on the balance sheet going forward, and with Griffin emerging as a beast below the foul line, Olshey knew his target was an All-Star point guard -- and he had one in mind. At a pre-draft camp in Chicago in May, 2011, he put out his first feeler on Chris Paul, whose player option was up in the summer of 2012.
The pursuit of Chris Paul
"Twenty-four hours after the pick goes from No. 8 to No. 1, I go over to [Hornets GM] Dell Demps," Olshey said. "I said, 'I don't want to offend you, but if the time comes when you find yourself in the same position Denver did with Carmelo [Anthony], I think we have more assets to transition an organization than anybody else. Please let me be your first phone call.'"
The 2011 lockout stalled talks because teams were prohibited from having contact with their players, and Paul would need to be consulted on any deal involving him. Most teams, the Clippers among them, felt they couldn't fully assemble an offer without knowing at least something about Paul's long-term intentions.
Once the work stoppage was over, there was a feeding frenzy for Paul, all of it played out under the uncertainty of the Hornets' structure of authority (the Hornets were owned by the NBA at the time). The Clippers were active in the talks, keeping constant contact with both Demps in New Orleans and Rose at CAA. Olshey created an offer for Paul in the event he'd opt into the final year of his contract, thereby assuring the Clippers Paul's services for two seasons. He also drew up a lesser offer if Paul wouldn't commit to more than one season with the team.
Olshey felt that, if given the opportunity to pitch Paul the way he'd pitched James, he could sell Paul on the opt-in. The Clippers would subsequently be able to extend the better offer to New Orleans, a collection of goodies -- expiring contracts, a young star, a quality draft pick -- no other team could rival. When that permission was granted by the Hornets, Olshey and Clippers coach Vinny Del Negro got on the phone with Paul.
"I was just blown away by how invested [Paul] was about our assets, our style of play, the pieces he would want once he arrived, what he would want to see us retain in terms of draft picks and cap flexibility," Olshey said. "You would've thought I was interviewing an assistant GM."
Paul knew there were a finite number of teams that could cobble together a package the Hornets could accept, and the Clippers were one of them. He wanted to get a glimpse of the Clippers' vision and imagine himself in the fold.
"I know who I am as a person," Paul said. "So I had more questions about the practice facility, and what the team looked like going forward."
The Clippers didn't get the opt-in commitment immediately after that conversation. With the Clippers unwilling to add to their lighter offer, the Hornets moved to work with the Los Angeles Lakers and Houston Rockets on a three-way trade. When that deal came off the rails, conversations between the Clippers, Hornets and Paul's camp resumed. Paul ultimately agreed to opt into the final year of his contract, which would guarantee he'd be under the Clippers control until the summer of 2013.
Over the next several days, Olshey slept very little while he and Roeser negotiated a deal that died and was reborn several different times, once when an official trade call with the league was imminent. On Monday morning there was yet another conversation, yet again no agreement. Olshey told the Hornets that the Clippers needed to move forward, but all the while Rose was in touch to encourage the Clippers to remain engaged in the talks.
After Olshey and Del Negro gathered their players in the film room to tell them no deal was in the works, Olshey returned upstairs to the executive offices, where Roeser filed a waiver claim on Chauncey Billups. Later that afternoon, the Clippers claimed Billups and matched an offer sheet on DeAndre Jordan. Two days later as Olshey picked up Billups personally at the airport and waited for him as Billups took his player physical, Demps called back to see whether the deal could be reconstituted.
Here was the tricky part for Olshey: He had sold Sterling on the notion that moving ahead and staying young -- with the addition of Billups -- was the best strategy. Backtracking on a strong proclamation like that can reflect poorly on a young executive. It's dangerous to lay out a vision to an owner, only to come back 24 hours later and contradict yourself.
With that in mind, Olshey told the Hornets that something needed to be added to the deal so he could present it to ownership as a different package. Two future second-round draft picks from the Hornets did the trick and Paul was Los Angeles-bound, and the opt-in came months later, according to Paul.
At a time when the franchise, its fan base and young superstar were celebrating , Olshey experienced a prolonged bout of agita. Billups, who was already less than thrilled to be amnestied by the Knicks then land with the Clippers, would have to be mollified again.
"It couldn't have gone worse initially," Olshey said. "Billups is the ultimate professional, but every time he turns around, someone is telling him something he doesn't want to hear about this Hall of Fame career that's at its culmination."
There was also Williams, who had agreed to opt in to the final year of his contract in 2012-13 because it appeared that he was the Clippers' starting point guard for the next two seasons. In 48 hours, Williams had dropped from first to third on the team's depth chart at the point. And the guys included in the deal were on a team bus, taking part in a community service event at a local hospital.
Gordon, who was the centerpiece of the Clippers' package, found the proceedings of that week distasteful and Olshey, in particular, disingenuous.
"He literally called a meeting to say that nobody was going to leave, that he loved the team." Gordon said. "He said it a couple of times. Then with a change like that? You really can't trust what the person says or does."
To make matters worse, the deal couldn't become official until Kaman arrived in New Orleans, and he wasn't a first-flight-out kind of guy. While the Clippers held an event that drew a raucous crowd at the California Science Center, Olshey was staring at his phone waiting for the official word from the league. Finally, late on Saturday afternoon, Dec. 17, the news came.
"It was the best email of my life," Olshey said. "All conditions of the trade were met. All players can begin practicing and off we went. And then it was real."
The snake charmer
If the acquisition of Paul yields the kind of fruit many anticipate it will for the Clippers, it will go down as one of the landmark deals in recent NBA history. Olshey recognized as much, but limited his self-praise.
"This deal took a lot of work and a lot of people worked a long time and put their blood, sweat and tears into it, but it certainly wasn't the most creative solution to a problem," Olshey said. "You have the best finisher in the league. You want the best passer in the league. How about we go get Chris Paul?"
Getting Paul into a Clippers jersey was Occam's razor in Technicolor, but problem-solving had never been a trademark of the franchise. To many on the outside, handing the keys to Olshey in the first place was classic Clippers -- fast, cheap and easy.
"I think at the beginning, it was a shock to 90 percent of the league," Vaccaro said. "It was totally out of the box and it startled the old-regime people."
What many of the old guard might not have recognized was what Olshey understands best about the job. Talent evaluation is important; so is the art of creative dealmaking and cap management. But the real trick to running basketball operations for the Los Angeles Clippers is internal salesmanship and, when you get down to it, it's an audience of one -- Sterling.
Olshey has cultivated his bona fides as a messenger with the media -- he has yet to lose a news conference in two years. He can be fairly described as handsome, even dashing. He abides by the smart, well-tailored combination of dark suit, light shirt. In a business in which many of his contemporaries revel in schlubiness, Olshey appears well-kept, a detail that helps his cause. But his real gift might be his ability, with Roeser's guidance, to sell his owner on a vision. Here's where Olshey feels that, ironically, his thin connections to the NBA establishment may work in his favor.
"This might be a case where the lack of pedigree in an asset," Olshey said. "Instead of coming from a position of 'This is who I am and you should listen to me,' I come from the, 'You've entrusted me to make recommendations to you. Here's why.' So we do a lot of research and write a lot of memos, whether it's free agency or the draft. And there's a lot of preparation that we do to get Mr. Sterling to the point of 'This is why we're recommending this deal.' I think that the investment we've made in prepping him for questions and decisions that we're going to need."
Planting seeds early has been Olshey's MO since he assumed his role, much the way it was at Artesia and with SFX. When he fell in love with Bledsoe, but knew it would require a deal to acquire him, Olshey started the process of educating Sterling in April 2010 so that shipping out a first-rounder on draft day for the Kentucky point guard didn't seem like an impulse buy.
"I've never seen [Sterling] not do something if there was conviction from the front office," Olshey said.
Sterling is one of the most reviled men in professional sports, for his record as a landlord, charges of racism, the chronicles of his extracurricular life and his unwillingness to make good on contractual obligations to some of his past employees. Olshey will counter that, when it comes to the business of empowering the front office to build a winner, he can't cite a proposed deal, expenditure or trade that, if presented with passion and backed up with numbers, was vetoed.
Olshey enumerated a catalog of such moves: the construction of the training facility; acquiring Davis as a free agent; approving the money for Brand; trading for Camby; trading for Zach Randolph; shipping out Al Thornton for expiring contracts; dealing Davis and the pick for Williams and cap space; Bledsoe; and, finally, trading Gordon, Aminu, Kaman and a pick for Paul.
What Olshey didn't say, but agents and other executives around the league have, is that he has a knack for internal salesmanship, for making a man like Sterling feel like an idea was his all along.
"If you don't have the trust of ownership, it's over," said one agent. "Neil, for the time being, has that trust."
Gazing into the future
Once upon a time, deep roots in the NBA were almost a necessity for someone to get the top job for an NBA team. Passion, love for the game, the ability to communicate -- all nice qualities, but they were rarely enough to score an opportunity like the one Olshey holds.
"He has one of the most unique backgrounds in the profession," Memphis Grizzlies general manager Chris Wallace said. "He turned an avocation into a vocation."
Hobbies that become professions are often fraught with risk, particularly when the job comes with this amount of stress, and the challenges ahead can't be understated. It's one thing to acquire Chris Paul, but quite another to retain him. If, in 14 months, Paul feels he's had enough of the Clippers or if Griffin decides he'd rather be elsewhere, the Clippers will be back at square one. The potential for success might be unprecedented, but so are the expectations.
"My job got harder, but easier," Olshey said. "It got harder because the bar got raised, way above where it had normally been with this organization because of the presence of Blake and the presence of, at the time, Eric [Gordon] and everything else. But it also got easier, because when I pick up the phone I can say, 'You want to play on national television and live in Los Angeles and play with a 22-year-old superstar?'"
There's mutual affection between Olshey and the Clippers. He's earnest in his gratitude to the organization, and the Clippers like that they've developed a homegrown product.
"At every juncture, he's been able to make the most of his opportunities," Roeser said.
Praise aside, Olshey isn't currently under contract with the Clippers. After his deal expired in October, he became what's known in the parlance of labor law as an "at-will employee." A paycheck still shows up in the mailbox, but either side can walk away at any point. The Clippers reiterate that Olshey is a cornerstone of their future, but if Olshey wanted to peddle his wares for a competitor, he could be on the next plane out of Los Angeles to a new job.
What's more likely to happen is that outside interest in Olshey will prompt the Clippers to secure his service for the long term. The Clippers have traditionally been a franchise that prefers to call rather than bet. They let the market set the price on talent, then decide whether they want to match that number.
The Portland Trail Blazers included Olshey in their executive search last offseason and he received positive reviews. Still, Los Angeles has been good to him. His wife is from California, and his two young sons attend school in Manhattan Beach. More than anything, the prospect of morphing the Clippers from a punch line to a paragon is his passion project.
"The thing that's most important to me and all of us is that we want players who want to be here," Olshey said. "Not 'They ended up here,' or 'They came here to get paid,' or 'I can get numbers there and then I'll move on.' What's important is that this is their destination. They want to be here. And I think we've finally turned the corner."