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In 1995, Shorenstein was involved in a transaction that also helped build Reilly's current fortune, selling his Prop. I campaign manager the 16-story Merchants Exchange Building in downtown San Francisco for $18 million. The building's value would be estimated at more than $70 million just five years later, according to an exhaustive 2001 profile of Reilly by SF Weekly's Peter Byrne.
As Reilly's net worth exploded, he went on a San Francisco politics spending spree, beginning gingerly with sundry cash gifts to causes such as the losing 1998 campaign to save the Central Freeway, then spending $4 million of his own money on a 1999 mayoral campaign that earned him only 12.5 percent of the vote. Reilly blamed his defeat on Willie Brown, whose campaign portrayed him as an unbalanced abuser of women. The following year Reilly sought revenge by spending tens of thousands of dollars on Board of Supervisors candidates and ballot initiatives opposed by Brown.
When the dust cleared, Reilly emerged as a local kingmaker, having been the major supporter of new Supervisors Tony Hall, Jake McGoldrick, Aaron Peskin, Sophie Maxwell, Chris Daly, and Gerardo Sandoval. He has remained their supporter and strategist-confidant.
Unlike other political mercenaries who ask for favors as soon as their chosen candidate takes office, Reilly has adopted a Svengali-Buddha approach to his political stock-picking. The consensus is that he has yet to ask supervisors for anything significant in return for his patronage, a stance that has only bound him tighter to his protégés.
In interviews for this column, even the most ordinarily straight-shooting of San Francisco politicians spoke with great deference for Reilly, citing his political wisdom, his selfless support for candidates and causes, and the public service potential, in her own right, of Janet Reilly.
If you want to see something neat, type the name "Megan Levitan" into the Google Internet search engine, and after the results come up, look at the top right-hand corner of the screen. Now try "Michela Alioto," or the names of any other possibilities for Newsom's District 2 seat. The paid Google advertisements that sometimes pop up in the corner of your screen are online political résumés for Janet Reilly, a former public relations flack, and for Clint Reilly himself.
The Reilly Web sites were recently registered by Andrew Hasse, who in 1999 cybersquatted on domain names potentially useful in that year's mayoral race, such as Williebrown.com, Williebrownsucks.com, and Clintreilly.com. At the time Hasse had hoped to become a political operative. Perhaps mindful of Frank Jordan's comment about Clint Reilly ("He's certainly better to have inside the tent than outside"), Hasse offered his services to both camps in that year's mayoral race, and Reilly brought him into the fold. It's safe to assume Reilly liked Hasse's style. "Attack, then embrace" has been Clint Reilly's hallmark political strategy, and it now appears to be playing itself out once again.
This spring, Clint Reilly hired an opposition research firm to do $30,000 worth of digging for skeletons in the closet of Gavin Newsom. Reilly then (it was alleged) stiffed the research firm for half the fee, the firm sued, the case made it into the papers, and suddenly it became public knowledge that the most feared political operative in California was assembling a black-book dossier on Newsom.
The possibilities were tantalizing. Did Reilly have dirt on Newsom's once-close relationship with and subsequent distancing from oil scion Billy Getty? Was there anything untoward in Newsom's Getty-financed business empire? What about the way Newsom's dad has managed the Gettys' holdings?
The next time Reilly's name surfaced in connection with Newsom, however, Reilly was being described as an important element within the mayor-to-be's campaign.
According to a variety of sources, all of whom asked not to be identified, Reilly provided fund-raising and strategic support for the Newsom campaign. He held at least one fund-raiser for Newsom, and he was occasionally seen around the campaign office. By press time neither Newsom's office, nor Clint Reilly, had returned calls requesting comment for this column. Whatever Reilly's role within Newsom's camp, that he did not support his progressive protégés as they backed the mayoral campaign of Matt Gonzalez was surely a key to Newsom's November victory.
Now, Reilly seems to be calling in favors.
Earlier this year, at the urging of Board of Supervisors President Matt Gonzalez, the supes appointed Janet Reilly to the Golden Gate Bridge Highway and Transportation District Board. According to a bridge board source, Reilly is the member who has the least knowledge about the transportation issues that come before the panel, yet the one given greatest deference by the other board members.
"They know she's married to this big-time political consultant," the bridge board member says.
Janet may well derive happiness from her marriage. But San Francisco will receive nothing but grief if it remains in bed with Clint Reilly.