Obama marketing campaign supervisor buys “Paypal Mafia” member’s residence

Former Obama campaign manager Jim Messina bought the Glen Park home from PayPal Mafia member Keith Rabois for $8.7 million, according to property and loan records.

Rabois launched the home in late 2020, shortly after the billionaire announced he was moving to Florida. The price started at $12 million, but after that multiple cuts had fallen to $10.25 million before the sale.

Even after losing a quarter of the original bid, the home is still the highest-priced sale ever made in San Francisco’s Glen Park neighborhood. According to Redfin data, there have only been six $5 million sales in the hilly area south of Noe Valley and east of Bernal Heights in the last five years.

Messina and his wife Taya Cromley, a clinical psychologist, closed the 5,700-square-foot home on Valentine’s Day, according to property records and loan documents Bank of the First Republic who list them as two members of SashaHouse, the Montana-based LLC that purchased the cul-de-sac home. The Obamas’ younger daughter is also named Sasha, but it’s unclear if she was the inspiration for the LLC’s name.

Messina lives in San Francisco and Montana with his wife and their two dogs, according to a bio on the website of his political consulting firm, The Messina Group. The site’s clients include Uber, Airbnb, Google and Delta Air Lines, as well as more than a dozen world leaders, including former British Prime Ministers Theresa May and David Cameron and former Mexican President Enrique Peña Nieto.

In the 2012 election cycle, Messina served as manager for Barack Obama’s re-election campaign, which used technology for public relations and fundraising. He was also deputy chief of staff in the White House under Obama.

Rabois also had a short-lived career in politics as an adviser to former Vice President Dan Quayle in 1999. A year later, he moved to Paypal, where he and other early payment site executives and founders such as Elon Musk and Peter Thiel became known as the “Paypal Mafia” due to the interconnected web of giant tech companies — Tesla, Uber, Pinterest, and Airbnb — that they later founded or in which they invested.

Rabois bought the home in June 2011 for $3.5 million while he was COO at Square and immediately submitted approval to fully develop the early ’70s hillside lot as a “breathtaking architectural development” with panoramic views of the city’s skyline to rebuild the city, according to the notes of Coldwell Banker’s Joel Goodrich and Camron Paul Garcia.

Garcia and Compass agent Steve Mavromihalis held the listing when it first went public, and Maveomihalis said via email that “we were able to secure immediate offers within the range of values ​​we had proposed to the seller, but were unable to complete a sale at that time.” Subsequently, he “backed out of that engagement,” he said, although Garcia stayed.

The home’s floor plan centers around an open-air atrium with a “mature birch tree, a flowing stream, and an outdoor shower,” according to the listing. The atrium has a one-car garage on either side of the top floor, and there are four bedrooms, five full baths, two half-baths, a media room, a library, a wine cellar with a sauna next door, and an outdoor hot tub spread across its four floors. The lowest level features a 700-square-foot gym with a half-bath and patio.

Rabois also plans to build a larger gym with a basketball court into another home he bought and is expanding across the street at 43 Everson. Despite moving abroad in 2020 and the ire of some of his neighbors who have urged the city to reject his “scale” plans, Rabois still owns this home, which was purchased in 2015 for $2.35 million, and seems to be moving forward with his Renovation. Electrical permits for AV systems, motorized blinds and automated lighting were recently approved, and gross plumbing inspections were also signed this week, according to city records.

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