Newsom’s Memoir Reveals Pattern of Reckless Behavior During San Francisco Years

California Governor Gavin Newsom admits in his new memoir to spending years drinking heavily and bedding a rotating cast of women while serving as San Francisco’s mayor—behavior he now pathetically characterizes as lacking “discernment.”

The Democratic governor’s confessional tome lays bare a troubling pattern of judgment failures during his tenure as the city’s chief executive. While taxpayers expected leadership, Newsom was apparently bar-hopping through San Francisco’s elite restaurant scene, guzzling expensive wine and pursuing romantic conquests with the zeal of a college fraternity president.

His routine was predictable and disturbing for an elected official: twelve-hour workdays followed by nights at restaurant bars, multiple glasses of wine, and what he euphemistically calls “new friends.” The next morning, he’d wake up believing his nocturnal activities were somehow “private matters”—a stunning display of naiveté for a public servant under constant scrutiny.

The Women He Won’t Talk About

What’s conspicuously absent from Newsom’s supposedly candid memoir? Any mention of Brittanie Mountz, who was just 19 years old when the 38-year-old mayor dated her. The omission speaks volumes about selective transparency.

The governor does discuss his relationship with actress Sofia Milos, whom he describes as “dark and seductive.” Despite warnings from his own staff that she was a Scientologist attempting recruitment, Newsom plowed ahead with the romance. It took a handwritten intervention from billionaire Gordon Getty—the oil heir who bankrolled both Newsom’s wine business and political career—to end the relationship.

That Getty felt compelled to personally pen a note warning Newsom that Milos “wasn’t right for him” reveals the concerning degree to which the mayor’s personal life was spiraling beyond professional boundaries.

The Affair That Should Have Ended His Career

Newsom’s most damaging admission involves his affair with Ruby Rippey-Tourk, his appointments secretary and the wife of his campaign manager and deputy chief of staff. Both were drinking heavily, according to the governor’s account.

After a party at his apartment, Rippey-Tourk was “the last to leave.” What followed was what Newsom minimizes as “the stupidest and also briefest of affairs”—a characterization that conveniently ignores the profound betrayal of a trusted aide and friend.

The scandal only came to light when Rippey-Tourk, to her credit, confessed to her twelve-step group a year later. Newsom was eventually forced to acknowledge the affair publicly, though he appears to have learned little from the experience.

His response? Attending counseling sessions at Delancey Street Foundation, only to receive a clean bill of health from a counselor who allegedly told him, “You can start drinking your f—king wine again.” If true, this represents either the worst substance abuse counseling in history or a convenient fiction.

A Pattern of Poor Judgment

The memoir also reveals Newsom’s relationship with Kelly Phleger, now married to actor Don Johnson, lasted roughly five years. He discusses early doubts about his marriage to Kimberly Guilfoyle, admitting he sat alone in a Plumpjack delivery truck questioning whether he loved her and whether she loved him.

That he proceeded with the marriage despite these fundamental doubts demonstrates a pattern of prioritizing political optics over personal integrity. Billy Getty, son of his benefactor, warned him to “be careful” with Guilfoyle before a couple’s trip to Hawaii—advice Newsom apparently ignored.

The governor eventually met his current wife, Jennifer Siebel Newsom, on a blind date in 2006. Siebel Newsom, now a feminist filmmaker, drew criticism for initially blaming Rippey-Tourk as “the culprit” in the affair with her husband. She later apologized, though the victim-blaming impulse revealed much about the couple’s instincts when confronted with inconvenient truths.

The Larger Question

Newsom’s memoir raises serious questions about the judgment and character of a man who aspires to national office. These weren’t youthful indiscretions—they occurred while he served as mayor of a major American city.

His casual dismissal of heavy drinking, serial relationships with increasingly younger women, and an affair with a subordinate married to a close friend reveals someone who believed the rules didn’t apply to him. The billionaire intervention required to end one relationship shows a man dangerously disconnected from appropriate boundaries.

California deserves better than a governor whose idea of candor is admitting to reckless behavior while conveniently omitting the most problematic details. America certainly deserves better if Newsom harbors higher ambitions.

The real question isn’t whether Newsom lacked “discernment” during his bachelor years. It’s whether he possesses the judgment, self-discipline, and moral compass required for executive leadership at any level.