But the skills that allowed Wiener to become a prolific legislator among his peers have not worked their magic on voters. Two of the three charter amendments he's placed on the ballot have been rejected. Most notably, Proposition E of 2011 was snubbed by 67 percent of voters despite its foes raising just $13,200 to combat it (tech investor turned moderate cash machine Ron Conway pitched in $10,000 toward the measure). In short, Prop. E would have enabled future Boards of Supervisors or mayors to amend or repeal future voter-enacted measures. Wiener will be the smartest guy in almost any room he walks into — but it's asking a lot of voters to essentially cede this point by allowing him and other elected officials to undermine measures they ratified at the ballot box. "I got my rear end handed to me on Prop. E," admits Wiener. "Voters always ask me, 'Why can't you guys do your jobs?' So I proposed a policy to see if they really meant it. ... We have a dysfunctional ballot system. I thought it was important to propose reform."
That sounds about right. Even in losing, Wiener can claim he was attempting to reform a broken system, while his opponents battled to retain the unworkable status quo. His subtle efforts to change the city's rules, akin to altering a few lines of coding within a vast program, could lead to drastic changes. But few can be bothered to parse those details. And, even when Wiener fails, he's never gotten into a wreck serious enough he hasn't walked away from it. Nothing has even slowed him down.
J. P. Dobrin
Those close to Scott Wiener say he's not "too uptight or too serious. ... He is very comfortable in his skin and very comfortable with other people."
Joe Eskenazi
Upon being sworn in as a supervisor in 2011, Scott Wiener realizes he is too big
for his desk.
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"Ninety-nine of 100 voters won't have a clue what [Prop. E] was about," explains Latterman, Wiener's longtime strategist. "I've said this to Scott over and over again: It doesn't matter if you lose or win. People will remember you did something. Here's the guy who's doing something.
"They've heard of him. He does shit. And they respect him."