Obama campaigner Jim Messina buys “Paypal Mafia” member’s home

Former Obama campaign manager Jim Messina has purchased “Paypal Mafia” member Keith Rabois’ Glen Park home for $8.7 million, according to property records and loan documents.

Rabois put the home on the market in late 2020, shortly after the billionaire announced he was moving to Florida. The price started off at $12 million but after several cuts had dropped to $10.25 million before the sale. 

Even after losing a quarter of the initial ask, the home is still the priciest sale ever logged in the Glen Park neighborhood of San Francisco. There have only been six sales above $5 million in the last five years in the hilly neighborhood south of Noe Valley and east of Bernal Heights, according to Redfin data. 

Messina and wife Taya Cromley, a clinical psychologist, closed on the 5,700-square-foot home on Valentine’s Day, according to property records and loan documents from First Republic Bank that list them as two members of SashaHouse, the Montana-based LLC that bought 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 for his political consulting firm, The Messina Group. The site lists Uber, Airbnb, Google and Delta Air Lines among its clients, 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 presidential re-election campaign, which used technology for outreach and fundraising. He also served as a deputy chief of staff at the White House under Obama.

Rabois also had a short-lived career in politics as an advisor to former Vice President Dan Quayle in 1999. One year later, he joined Paypal, where he and other early executives and founders of the payment site like 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 — they later founded or invested in. 

Rabois bought the home for $3.5 million in June 2011 when he was the COO at Square and immediately filed permits to completely rebuild the early ‘70s hillside property as a “stunningly architectural compound” with panoramic city skyline views, according to listing notes from Joel Goodrich and Camron Paul Garcia of Coldwell Banker. 

Garcia and Compass agent Steve Mavromihalis held the listing when it first came on the market and Maveomihalis said via email that “we were able to secure immediate offers well within the value range we had suggested to the seller, but could not consummate a sale at that time.” He subsequently “stepped away from that engagement” he said, though Garcia stayed on. 

The home’s floor plan centers around an open-air atrium with a “mature birch tree, running brook and outdoor shower,” according to the listing site. The atrium has a one-car garage on either side of its 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 view hot tub spread out over its four floors. The lowest level has a 700-square-foot gym with a half bath and a deck. 

Rabois also plans to put a larger gym with a basketball court into another home he bought and is expanding across the street at 43 Everson. Despite the cross-country move in 2020 and the ire of some of his neighbors, who asked the city to deny his “out of scale” plans, Rabois still owns that home, purchased for $2.35 million in 2015, and appears to be moving ahead with his renovation. Electrical permits for AV systems, motorized shades and automated lighting were approved recently and rough-in plumbing inspections were signed off this week as well, according to city records.

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