Trump advisor Scott Adams’ career influencd by passionate love affairs
Scott Adams, the Dilbert cartoonist, was one of the most influential political pundits in America. He also had a spectacular love life.
Many of his fans knew about his two marriages, both of which ended in divorce. But, few knew that he also had enjoyed several passionate relationships that shaped his career. When Scott asked me to write his biography — “Scott Adams: A Life of Persuasion and Principle” (out now) — late last year, just weeks before he died, he gave me a list of people from his professional life.
He mentioned people who helped him launch his Dilbert cartoon. He suggested I interview close advisers to President Donald Trump, whose victory Scott famously predicted in 2015. Scott also encouraged me to talk to people who had put his self-help teachings to good use, across fields from journalism to medicine. But he didn’t mention his former girlfriends.
I had no intention of writing a “tell-all” biography about Scott, who had become one of my best friends. Yet, as I combed through his archives, it was impossible not to see the role that love had played in his life.
One of Scott’s most important relationships was with Pam Okasaki, whom he met when they were both working for Pacific Bell in California — right before Dilbert went big.
They ended up dating for 15 years, and sharing a home in the East Bay. Pam was his companion as Scott made the transition from obscure engineer to world-famous cartoonist. She helped him come out of his shell, socially, and built a large, boisterous network of friends around him. Scott struggled with his new life as a celebrity. He turned down invitations to party at the Playboy Mansion and fly with the Navy’s Blue Angels. But Pam encouraged him to take up one invitation, a cameo appearance on Babylon 5, the sci-fi TV show.
Over time, they grew apart, and they eventually split. Scott used to say that he had no regrets in life. But, he struggled with the end of that relationship.
He soon found new romance: He fell in love with his assistant, Shelly Miles. They married in 2006, and Scott became a stepfather to her two children. It was a role he relished, writing humorous notes for the kids every morning and savoring their sporting pursuits.
Shelly and Scott later split, she recalled, because he had developed a sense of mission about his work and turned inward. But, they remained close friends, and she returned to work for him. In his last months, she was one of his round-the-clock caregivers.
Just weeks after Scott passed away, Shelly died suddenly of a heart attack. Theirs was a bond that transcended this world. I was told — erroneously — that another one of Scott’s girlfriends had likely passed away — his college sweetheart, about whom he had written in some of his books.
She was the reason Scott ended up in San Francisco, where he launched his business and cartooning career. She was Scott’s first love — and his first heartbreak. I wanted to talk to her to learn more about who Scott was as a young man. I wanted to connect with someone who loved him before he was rich, and famous, and advising world leaders.
She had left no online trail, no public records. Someone told me to check the obituaries. The next day, I found her — alive and well. As Scott’s biographer, and a friend, I had to handle these topics carefully.
But there was something fundamental about him that I wanted to share.
Scott was skeptical about marriage — an institution he said was poorly designed.
But, he never lost his faith in love.
Joel Pollak is Opinion editor of the California Post.