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By the time Steve Ballmer’s oldest son reached his junior year at Lakeside School, the basketball program was in disarray.

The Lions finished the 2008 season with just two wins, losing every game within a Seattle league that was otherwise producing NBA talent. One loss was by a margin of 66 points.

An elite private school with an endowment of $190 million, Lakeside was better known for its academics, chess team and being the place where Microsoft co-founders Bill Gates and Paul Allen began their alliance as students in the late 1960s.

Ballmer, however, was a basketball zealot who had been angling to own an NBA franchise, a goal finalized just last week with his $2 billion purchase of the Los Angeles Clippers. Before he had a pro team to call his own — and with all three of his kids involved with basketball at Lakeside — Ballmer focused his attention on the high-school team.

Ballmer and his allies at Lakeside attracted basketball talent to the wealthy school and aided them with a series of questionable tactics that included a new basketball-focused nonprofit, cash for a coach, an unusual admissions process and weak enforcement of academic standards. One star player stayed at a $6 million mansion as he shuffled through three years of an academic schedule that almost ensured he wouldn’t get a Lakeside diploma.

“They relaxed their academic integrity to accommodate athletes,” said Dana Papasedero, who coached baseball at Lakeside for two decades.

The tactics may have violated Washington state’s prep-sports rules, according to a Seattle Times investigation. But it all paid off: In just five years, Lakeside went from winless in its district to district champs for the first time in a quarter century.

The Lions kept winning all the way up until an overtime loss in the 2013 state title game — the best finish in school history.

Basketball aspirations

Ballmer, who spent his high-school years at Detroit Country Day School, grew up playing basketball and wishing he had the skills to do it well.

Even as he rose up the ranks at Microsoft, where he was CEO for 14 years, Ballmer sought counsel to improve his game. The software company and the Seattle SuperSonics shared workout space in Bellevue in the early 1990s, allowing Microsoft executives to build relationships with local basketball players and their workout guides.

One of those Sonics advisers was Steve Gordon, a gregarious gym rat nicknamed Hat Man who ran basketball workouts for NBA stars, local executives and the children of both groups.

For years, Gordon led grueling 6 a.m. sessions with Microsoft executives, beginning what would become a deep friendship with Ballmer.

When Ballmer had his 50th birthday party with an exclusive guest list, Gordon was there to celebrate. Over the years, Ballmer paid for things like Gordon’s medical expenses, airline tickets, hotel rooms, legal help and a financial consultant.

The ultimate fan

Ballmer became the ultimate fan at his kids’ games, bellowing supportive cheers and comments at a volume that verged on obnoxious.

But in private, Ballmer expressed frustration with the team’s terrible performance, according to a sworn deposition from Gordon in a lawsuit that targets the two men over a business deal.

In the car after one of his son’s particularly bad games, Ballmer fumed about how Lakeside’s coach was managing the team, according to Gordon’s March deposition. During his rant, Ballmer began plotting a way to bring in new personnel.

“I’m going to open up a foundation, and we’re going to get black people in here,” Ballmer declared, according to Gordon’s testimony from March.

So the two set out to make it happen.

Cash payments

In November 2008, Lakeside brought in a new assistant coach, Tavio Hobson, who had met Ballmer a few years prior and had led workouts with Ballmer’s oldest son. And Gordon said in his deposition that he began providing Hobson about $800 a month in cash to supplement the pay the new coach was receiving at Lakeside.

Gordon said in the deposition that money came from large monthly payments Ballmer sent to him. Ballmer said he began paying Gordon $9,900 a month some years ago as a gift to help a friend in need. Gordon said he considered the money a “stipend” for doing work on Ballmer’s behalf. He had two Wells Fargo accounts over which Ballmer had power of attorney.

Gordon had told Ballmer he was “taking care” of the Lakeside coach, Ballmer said in a legal document in the business dispute, but added that he didn’t ask Gordon for details about what he meant. Hobson recently said Gordon was paying him — sometimes a few hundred dollars a week — to help train kids.

“I was trying to figure out a way to make a living doing what I loved,” Hobson said in an email interview.

Hobson became the team’s head coach in June 2009 after Lakeside promoted the previous coach to athletic director.

Gordon continued making the cash payments until a nonprofit foundation, A PLUS Youth Program, was set up in October 2009, according to Gordon’s deposition. It provided the coach with a more consistent second income.

The nonprofit

A PLUS quickly gave Hobson visibility in the basketball community and connected him with local basketball stars Brandon Roy, Martell Webster and Jamal Crawford.

Hobson joined forces with local basketball coach Jerry Petty, who had been running his own program in the area. Petty’s program needed money, so he welcomed a merger with A PLUS.

Ballmer became the lead booster of the nonprofit, matching every dollar that was contributed, Petty said. The program raised over $1 million in less than three years, according to IRS records.

Other A PLUS supporters have Lakeside ties.

The seven members of the nonprofit’s “advisory council” include Ballmer and his sister, Shelly. Another is Eddie Poplawski, who recently had a son playing basketball at Lakeside. Another is Paul Pigott, who has coached basketball in the community, had a son on the team at Lakeside, and comes from a wealthy family for which buildings on the Lakeside campus are named.

At least four people — Hobson, Ryan Webb, Shea Robinson and Aaron White — worked as staff members at A PLUS while they were helping coach basketball at Lakeside.

Four current Lakeside basketball players are A PLUS members. State rules restrict high-school coaches in the offseason; they cannot “sponsor, coach or direct activities which resemble out-of-season practices or contests” with their students or middle-school students from their feeder school. Hobson said A PLUS is in full compliance.

Petty eventually left the program, in part because he felt that too much of the nonprofit’s money was going to personnel and not enough was going to the kids.

Hobson said A PLUS “is far from a vehicle to attract kids to Lakeside.” It has evolved to an organization that serves 180 participants, most of them students of color, at 50 schools in 14 districts, with a program GPA of 3.14. A PLUS “is as much about learning and character as it is about athletic achievement,” he said in an email.

He added that 14 A PLUS members have been admitted to private schools in the past five years, with only one going to Lakeside.

Gordon declined to comment for this story. Ballmer also declined to comment, citing ongoing litigation. Ballmer has recently accused Gordon of falsely representing his ties to the billionaire during a business deal. One of Ballmer’s attorneys said in a legal filing that Ballmer referred Gordon’s conduct to local prosecutors for investigation.

Ballmer attorney Mark Rising said the lawsuit involving the two former friends appears to be an effort by Gordon and another man to get money from Ballmer.

Lakeside connection

In just his second year as head coach, Hobson was already improving Lakeside’s basketball performance, thanks to some talented new players at the school.

Prep-sports rules in Washington state say schools, whether private or public, can’t even “encourage any prospective student to attend or continue to attend any member school for the purpose of participating in athletics.”

D’Marques Tyson recalled that Hobson was the one who first approached him about coming to Lakeside.

Tyson, who grew up in Bothell, described how he eventually “went on a visit” to the school, where officials made clear they had a renewed emphasis on the basketball program. Tyson saw Hobson as a new coach who was respected.

“The basketball program was turning around,” said Tyson, team captain of Lakeside’s squad that went to the state championship. “That was a huge draw for me.”

Tyson said Hobson also talked to Tyson about the academic rigors of Lakeside. Hobson said it was Tyson’s family who first approached him about coming to the school.

Classroom struggles

Another player who joined the school was Tramaine Isabell, a talented prospect who is now set to play at the University of Missouri.

Isabell’s mother, Aiyana Brown, said he first became interested in Lakeside after his middle school took him on a trip there. As a single mother and bus driver, she knew that the cost of the school was beyond her reach, so she asked Isabell’s basketball trainer, Jeff Harris, to check with people he knew at the school.

Harris said he called his old friend Hobson, the new head coach. Harris said he and Hobson talked about the difficulties they would face if Isabell came to Lakeside.

“Tavio was kind of like, ‘Are you sure, Jeff? Are you sure that this is a kid worth sticking our neck out on the line [for] and trying to help?’ ” Harris said.

Isabell started as an eighth-grader.

Isabell said the experience at Lakeside was “crazy” because people like Ballmer were among his biggest supporters. He described becoming “close friends” with the billionaire, who would ask Isabell about how his schooling was going.

The academics were a challenge. Isabell’s GPA was always close to 2.0, or C, his mother said.

Brown described her son as “kind of like a guinea pig” for Lakeside as the school explored ways to be more diverse. “Tramaine wasn’t necessarily ready for Lakeside,” Brown said. “I don’t know if Lakeside was necessarily ready for him.”

To help get him through the first year, Lakeside assigned Isabell a tutor that ended up working with him two hours a day, five days a week for three months. He also had the help of tutors in other years.

State rules require student-athletes to maintain at least a D grade in all but one of their classes, but many schools or districts have a more stringent standard that the state considers a superseding requirement. Seattle Public Schools, for example, requires that athletes have a 2.0 GPA and take classes that move them in “normal progress toward graduation.”

Carol Puccinelli, the Lakeside athletics secretary when Isabell was a student, believed that the 2.0 standard was in place at Lakeside under the athletic director who hired her, Ed Putnam, who died in 2008. Booth Kyle, the current admissions director at Lakeside, said he has no record of that standard ever being in place and that the school currently follows the lower state standards.

Puccinelli was surprised by how much time Isabell was spending in the gym during school days, since skipping class would prohibit a student from playing in a game. And she showed people in the athletic department that Isabell’s grades might make him ineligible.

Administrators never deemed Isabell ineligible. Instead, Lakeside kept advancing Isabell through his freshman, sophomore and junior years. Puccinelli recalled a conversation with a Lakeside teacher who said Isabell was being allowed to hold off taking some of the academic classes that he would need for graduation.

Because of that, Isabell’s senior-year schedule would have been an enormous undertaking, Puccinelli said. That almost ensured Isabell would not get a diploma from the school.

Isabell left Lakeside before his senior year, just a few months after leading the team to the state title game.

Puccinelli said it was sad to watch Isabell struggle. “It wasn’t fair to him,” she said.

At the end of each season, Puccinelli had the task of submitting each Lakeside team for state academic awards. One year, she couldn’t figure out why the system wouldn’t accept the basketball team’s grades, until she learned that the minimum standard was a team average 3.0 GPA.

The basketball team had fallen to a 2.8 — something Puccinelli hadn’t seen in her 14 years there.

A home on the lake

Isabell also got help at home, thanks to Rich Padden, a wealthy lawyer who has been a major supporter of the nonprofit funded by Ballmer, has been involved closely with Lakeside athletics, and had a son on the Lakeside team.

Padden “took an interest in me,” Isabell said. The player began living at Padden’s home — a $6 million mansion on Lake Washington that includes nearly 6,000 square feet of space.

In an interview, Padden initially declined to describe Isabell’s living situation at the Washington Park house. He later said Isabell would “periodically stay with us” in the middle of the week.

When a Times reporter obtained records showing Isabell’s driver’s license listed Padden’s house as his home address, Padden acknowledged that Isabell stayed there “most of the time” and is still living there today, even though Isabell is out of high school.

Padden also said Isabell was allowed to use one of Padden’s vehicles — a GMC Yukon the player was driving when he got pulled over earlier this year two hours south of Seattle, according to court records. Padden also said he gave Isabell a “modest” amount of money to help him buy things like gas and food.

Isabell’s mother said Padden helped with some medical bills related to a critical surgery the player had to rebuild his injured ankle.

Padden said he simply wanted to help a young kid who came from a difficult upbringing.

“Anything I believe we can do to help the black community in Seattle is kind of where my focus is,” Padden said.

The circumstances have similarities to the case of Jamal Crawford. A Seattle businessman supported Crawford with a car, a place to live and money while he attended Rainier Beach High School. The NCAA later suspended Crawford for violating rules concerning amateurism.

State amateurism rules say players cannot accept “in-kind gifts of more than $300 in fair market value per sport during any one calendar year.”

Legacy of achievement

On Lakeside’s campus, the expanded focus on athletic success was clear to everyone.

Ballmer’s wife, Connie, had been serving on the board of trustees for several years and rose to become the board’s chair in 2010. She began her tenure with a message to parents that included talk of improving athletics.

In just a few months, the board of trustees approved new athletic goals that included: a plan to “strive for competitive success”; a program that would “create a legacy of achievement”; athletic facilities that would “attract” students; student-athletes who would develop to “high levels of achievement.”

To meet the goals, the school later strategized to “prominently feature athletics at all stages of the admissions process,” according to one document.

As the plans developed into 2011, Connie Ballmer wrote in one message to Lakeside supporters that they would start to see “program improvements” in the new school year. She acknowledged concerns in the community, saying the board had “many spirited conversations about resisting our culture’s pressure to make sports all about winning.”

She went on: “And we want to ensure that the level of academic rigor at Lakeside is not compromised just to win a title.”

Shortly afterward, the school got $16 million in donations from “a small group” of anonymous donors that went toward a massive new athletic complex that would ultimately include classrooms with interactive projectors and a 336-square-foot projector screen for the gym.

“An eye-opener” for coach

It was also clear that the values of the athletic program were changing, said Bill McMahon, who recently left Lakeside after serving 40 years as a football coach and 20 years on the school’s admissions committee.

As winning became the “focus,” McMahon recalled that an administrator suggested to coaches that they push the limits of prep-sports rules by attending sports events involving talented child athletes and wearing Lakeside apparel when meeting with the kids and their parents. Because it seemed like an inappropriate form of recruiting, McMahon said he objected.

On the Lakeside admissions committee, McMahon was one of the people who waded through hundreds of applications to select the elite crowd that would enroll each year. McMahon said at least two basketball players — he declined to say their names — were enrolled without being considered by the committee.

McMahon said he questioned school leaders about that unusual development, and he recalled someone telling him there were late openings at the school and that the students were admitted at the end of summer.

“It was a little bit of an eye-opener for me,” McMahon said.

Kyle, the Lakeside admissions director, said every student he has seen during his tenure has gone through the standard admissions process.

McMahon and Papasedero, the baseball coach, both remembered some of the athletes who were having difficulties in the classroom. Some of Papasedero’s players questioned why other athletes at the school didn’t have to follow the same academic standards, including one who flunked a 30-question exam but was allowed to play in a game later that same day.

Papasedero said he was heartbroken to see how the school’s changes impacted the kids he coached. “I feel they have strayed from their core values,” Papasedero said.

Papasedero resigned this year after a meeting with the athletic director, who questioned whether he’d won enough and wondered why he wasn’t connecting with students on social-media platforms like Twitter. He finished the season and earned the title of 3A Coach of the Year.

Papasedero believes that in a push to win at sports, the school may have “stepped over the line” when it comes to state prep rules on academic eligibility.

The aftermath

Two of Ballmer’s three sons have now graduated Lakeside.

The basketball team that went to the state title lost some of its key players. Tyson left for North Carolina, saying he thought the East Coast would give him more basketball exposure. Isabell left for Garfield High School.

In their place, talented athletes continue to join Lakeside’s basketball program, including Isaiah de la Fuente, who originally started at Hobson’s nonprofit.

Ballmer and Hobson remain close, with the billionaire participating earlier this month in a golf event that raised funds for A PLUS, which has grown into a large organization that helps scores of students with tutoring, sports and other services.

Ballmer and Gordon, meanwhile, have had a falling out.

Ballmer said in a legal document that Gordon betrayed their friendship, saying Gordon had used people to impersonate Ballmer on phone calls. Both men are now named in a lawsuit related to a bad business deal.

Now that he owns the Clippers, Ballmer will begin his tenure Monday with a fan festival in Los Angeles. He promised to give the team all the support it needs.

“I will be hard core,” he said.