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There’s a story Paul Freedman tells about playing basketball at Ohlone Park with his high-school friend Bobby Winslow. Unlike the usual lay-up where, if all goes well, ball meets backboard, hand brushes net, and two points are chalked up – Bobby could drive the hole like a pro. “Bobby was an incredibly graceful player,” said Freedman. Five-foot-eleven and slender, Winslow may not have been an obvious candidate for the fly-through-the-air-with-the-ball-behind-your-back acrobatics of their idol Michael Jordan, but in basketball, as in life, Bobby was exceptional.  

“Bobby could fly,” recalled Freedman, 22. “He probably had the best jump shot I’ve ever seen in a pick-up player.” And while his friends remained in the ranks of junior varsity basketball, Bobby made varsity his sophomore year. “There were numerous times when the coach gave Bobby the ball at the last minute,” Freedman said. “If Bobby makes the shot, we’d win – if he misses we’d lose.” They usually won.  

Robert Kim Winslow won at most things. The only son of Robert and Jennifer Winslow, Bobby grew up in a small two-bedroom apartment on Hearst Avenue, in west Berkeley. His father worked as a salesman at Levitz Furniture, and his Korean-born mother was an assistant in the University of California president’s office. Though they couldn’t afford their son’s private education, through scholarships and his parents’ sacrifice, Bobby managed to attend Bentley Middle School, and later, the prestigious College Preparatory School, both in Oakland. He graduated with honors, winning an award for academic and athletic excellence. He then went on to Yale, where he majored in economics and won an award upon graduation for kindness, dedication, and courage.  

After graduation Bobby took a job in Manhattan with Goldman Sachs. Everything seemed to be going his way – he had just passed a test to trade securities for the firm, and he was on his way to realizing his dream of buying his parents a house of their own – when he collapsed while jogging in Central Park. Unknown to Bobby, his friends and family, he was born with a misrouted artery exiting his heart. Its circulation was momentarily blocked, and he died in the park Sept. 9, 2000, 13 days after his 22nd birthday.  

A year after his death, Bobby’s friends and family have won approval from the Berkeley City Council to erect a memorial and rename the basketball court at Ohlone Park in his honor. His friends are designing the plaque, and they plan to finance the memorial without the city’s help. 

Bobby’s friends say they’re still amazed that with his superior basketball skills, he continued to play with them throughout high school. But skill was only part of their games’ meaning. In the coded languages teenagers create, basketball became their lingua franca. “When we played basketball it was a reflection of our personalities,” said Noam Pines, 23, another of Bobby’s friends. They were classmates at CPS, but the court was where they said they got to know each other. It was the place they went when they wanted to escape the pressures of home and school. They talked about their lives while taking free throws. They spoke of their futures while practicing jump shots. And, of great importance to 16-year-old boys, basketball was an excuse to ham and goof with friends. Bobby was the group’s center. “We needed to tease him about something,” said Freedman. “He just didn’t play defense very hard.”  

On the court and in the classroom Bobby was a leader. “To all of his friends he was a role model,” said Freedman. Friends say he taught them determination and kindness. “I can’t even start to list all the things I’ve learned from him,” Freedman said. “I say things all the time and I’m like, ‘I got that straight from Winslow.’”  

Kids from the neighborhood also gravitated to Bobby and the court. Guyve Shalileh, his downstairs neighbor during high school, said that whenever he heard Bobby bounce the ball down their apartment-complex’s stairs, he knew it was time to play.  

Bobby cared about school, and, say friends, his passion for learning rubbed off on them. Shalileh, who is now a student at UC Berkeley, credits Bobby for getting him interested in school. “He could always fit everything in, he could make the day longer,” said Freedman. “Bobby showed a way that you could study really hard and achieve traditional forms of success, and not give up cool.”  

And by all accounts, Bobby was cool. Friends say his sense of humor made people feel comfortable. “He would find tremendous humor in little tiny things,” said Freedman. He loved to play on words, and friends say he had an inside joke with everyone he knew. After mercilessly teasing Bobby one day for coming home from college wearing dress shoes, Pines showed up to a game wearing rugged brown sneakers reminiscent of hiking boots. “Every time I missed a shot, Bobby was like, ‘what’s up Hikel Jordan?,’” Pines said. “Every person that was his friend considered him one of his best friends.”  

The point was reinforced by Freedman, who figures that in high school he spent more time with Bobby than away from him. “Being Bobby’s friend was also an incredible letter of recommendation for people,” he said. “You gave people a lot of slack just because they were friends with Bobby.” 

But Bobby wasn’t all basketball, jokes, and school. He also played classical and jazz piano. He had a weakness for California rolls, and he was bowled over when he found out his mom had taken a sushi-making class. His mother said he was an extraordinarily loving son who appreciated little things as much as large. “Every single meal he sincerely appreciated,” said his mother Jennifer. “Whenever I wanted to give him something he said, ‘Mom, I don’t need it.’ But whenever we gave him something he really appreciated it.” 

He was also very close to his father, and was deeply affected when Robert Winslow suffered a stroke in 1996. “He took on his father’s sickness as another responsibility,” said Freedman. Bobby began leaving the court early so his father wouldn’t be left unattended. His mother said that although he had planned to go to Yale, when his father became ill he decided to go to Stanford instead. He wanted to be able to come home to help on the weekends. “I told him, ‘Son, you’ve got to live your life,’” she said. Bobby reluctantly accepted Yale.  

It’s been a long year for Bobby’s friends and parents. But the renaming of the court at Ohlone Park is only one of many honors bestowed on him. “Every place he’s been they’ve wanted to do something to honor him,” Freedman said. Yale has named an award after him. His high school is erecting a memorial in his honor.  

But the court on Hearst is special. “Anybody that played on the court knew it was Bobby’s court,” said Freedman. He said one of their favorite activities during high school was to watch a video called “Michael Jordan’s Playground,” (which Freedman described as “a video for ridiculous fans”). “Bobby always said this was ‘Bobby Winslow’s playground.’”  

Freedman and Pines plan to erect the plaque within the next month. When they conceived the project they were concerned that the city would say no because Bobby was so young when he died, and hadn’t done many of the things people who are memorialized usually do. Still, they went ahead with a neighborhood petition and approached the City Council. “If there’s any kind of person that you’d want to commemorate, this is the kind of person,” said Freedman. “Not only is this a great honor for Bobby, it’s a great honor for the city of Berkeley.”