Still, fewer pages than Hillary

Making the distinction between personal and public emails has been difficult for San Diego city attorney Jan Goldsmith. In recent years Goldsmith has admitted to his use of private email accounts to conduct city business. The practice of using private emails to discuss city matters resulted in a lawsuit from watchdog group San Diegans for Open Government and its attorney Cory Briggs.

A newly released court transcript from that case shows Goldsmith relied on his private email account far more than he and his attorneys have let on. Earlier this month, judge Joel Wohlfeil ordered the city to turn over 25,000 pages of emails that Goldsmith sent on his Yahoo! account, a far cry from the 962 emails that the city has so far released.

In recent depositions, Goldsmith testified that he had a "practice of emailing, from the city email system, reading material to my personal email account for later review...comparable to bringing home copies of reading materials, but saving copying costs."

In that same December 2014 deposition, Goldsmith attested that he made sure he included his work email address so the communications would be documented. That doesn't appear to be the case.

According to a February 19 court transcript obtained by the Reader, since taking office, Goldsmith has written thousands of emails on public policy during and after work hours on his private account to his colleagues on the League of California Cities.

The league is comprised of elected officials from cities and counties throughout the state. City attorneys from throughout the state are also members of the club. The attorneys discuss and advocate for city and county policies such as medical marijuana enforcement, the wind-down of redevelopment agencies, and vacation rentals, among other topics.

Over the years, Goldsmith has fallen in line with the recommendations from the league; namely, in opposition to the proliferation of both recreational and medicinal use of marijuana as well as the tight controls that the state has imposed on the use of revenues from the former redevelopment tax. In both cases, Goldsmith has devoted an abundance of city resources in an attempt to shape city policy.

Attorneys for Goldsmith have tried to keep the related emails from seeing the light of day. They argue that emails between members of the League of California Cities should be considered privileged because they discuss legal issues that cities face. According to deputy city attorneys handling the case, even if "the emails do pertain to city business, they're privileged." Attorney Briggs doesn't see it that way.

While addressing judge Joel Wohlfeil during a February 19 court hearing, Briggs said that if the emails are privileged, the city should be required to state exactly why they are privileged and redact the information that is off-limits while releasing the remainder.

Briggs also argues that the city attorney's only client, according to Charter Section 40, is the City of San Diego. In other words, the city attorney can't claim attorney-client privilege when discussing city business with the League of California Cities because the league is not Goldsmith's client.

"There's not even an offer to do the redactions," Briggs said during the hearing. "We're not interested in knowing who the other members of the League are. Never mind that it's the League of California Cities, so they're public agencies. City Attorney of San Diego is a permanent member of the League's legal advisory committee. Charter Section 40 makes the City Attorney of San Diego the City Attorney for San Diego. If the City Attorney of San Diego is having conversations with people who aren't the lawyers for the City of San Diego, by definition, that can't be attorney-client privilege. By definition, it can't be attorney work product privilege. He's having a conversation, at best, with colleagues. That's not privileged."

Aside from saying the emails are private, deputy city attorney Catherine Richardson says compiling the 25,000 pages is a daunting task.

"...[W]e are not talking about five or ten, 50, even a thousand emails," Richardson said during oral argument. "We're talking about 25,000 pages of e-mails…. Well, it would be 50 binders of e-mails. And that was not something that I wanted to inflict on the Court. So I do have a CD. But the point of all that is, we're not talking about a few e-mails. We're talking about a lot of e-mails. And the bulk of those e-mails are these League of California Cities e-mails. And for us to have to go through all of those e-mails and redact them or review them again to decide — to see whether in what portions of them should be produced or not produced, that would be a burden that would be so out of proportion to any value or public interest that there would be in those documents….”

In the end, however, judge Wohlfeil disagreed that the emails are privileged; on the contrary, the city attorney has the burden to show exactly why they are privileged.

"However, confidential does not mean that it's privileged and the participants can, upon a proper request, claim a privilege and refuse to disclose it…. I’m not at all convinced that that is a basis to withhold materials that were exchanged between the participants of the League, at least not upon a proper request, as appears to have been done in this case."

Now, the city attorney's office has 45 days to produce the emails, with proper exemptions. In the meantime, the city attorney's office, according to the transcript, says they plan to file a motion for sanctions against Briggs. A previous attempt was dismissed.

To read more stories on City Attorney's private email dilemma, read the July 14, 2014, September 15, 2014, January 27, 2015, stories.