To The IRS Regarding 48 Hills

This piece also ran as part of Heather Knight’s column in the San Francisco Chronicle on May 23rd, 2017. A point that I should correct is that 501(c)(3)s actually do pay payroll tax. However, the nonprofit entity itself does not pay federal income tax, and of course donations are tax-deductible for donors, which is the main benefit.

To the IRS and the public,

48 Hills is an independent publication run by the San Francisco Media Center (SFMC). Its editor and executive director, Tim Redmond, writes about San Francisco current events and politics. SFMC is also an IRS-approved 501(c)(3) nonprofit entity, which not only exempts SFMC from paying taxes on Tim Redmond’s salary, but also grants a tax deduction to any donor who contributes to 48 Hills. This would all be well and good if it weren’t for the fact that 48 Hills routinely engages in one of the acts expressly forbidden to a 501(c)(3): electioneering.

The IRS is crystal clear on this mandate: “Under the Internal Revenue Code, all section 501(c)(3) organizations are absolutely prohibited from directly or indirectly participating in, or intervening in, any political campaign on behalf of (or in opposition to) any candidate for elective public office.” 48 Hills as a publication is a unilateral supporter of the “progressive” faction of the Democratic party in San Francisco, and does not hesitate to attack any politician outside of this camp. This is not a free speech issue. Most SF newspapers are not incorporated as 501(c)(3)s and do not receive special tax treatment. 48 Hills is quite likely the only SF politics-focused publication that also happens to be a 501(c)(3).

Background (San Francisco Politics)

San Francisco is a very liberal city. All of its elected officials are currently, to my knowledge, Democrats. Although not formally institutionalized, there are two main political factions in San Francisco, which are generally described as the “progressives” and the “moderates.” Both are still Democratic groups, but often differ significantly in their opinions on public policy. A relatively neutral explanation of both parties is that moderates are more in favor of public-private partnerships, and progressives are more leery of industry and privatization.

In a March 2016 piece entitled “Two-Party Town,” Tim Redmond himself identifies the two parties and his preference for one of them:

I am increasingly coming to believe that San Francisco is now a two-party city – and oddly, we are seeing that reflected in the race to determine who will run the Democratic Party.

Republicans are almost entirely irrelevant in San Francisco (the last GOP office holder, BART Board member James Fang, lost his seat two years ago. There hasn’t been a Republican in any significant elected office in years). There’s a modest Green Party…

But the real two-party system right now is between the progressive party and the Ed Lee/real-estate/tech mogul party…

But overall, they are two very distinct parties – and you aren’t going to see much crossover in endorsements, political activism, or political fundraising this fall.

Indeed, 48 Hill’s endorsements are almost exclusively “progressive.” The 48 Hills website describes itself as “the progressive daily that San Francisco has always needed” whose writers and editors are “proud of [their] politics.” Moreover, in his “Two-Party Town” piece, Redmond adds:

Progressives are often fractious, and that’s fine – we argue, we care about policy, we aren’t afraid to disagree. But right now, the progressive community is pretty unified around the June and November elections. (Emphasis added.)

Simply put, 48 Hills self-identifies very strongly with just one particular political group in San Francisco.


The IRS ban on 501(c)(3) electioneering is absolute, which means not even “a little bit” of campaigning for a candidate is allowed. Again, the relevant section reads: “501(c)(3) organizations are absolutely prohibited from directly or indirectly participating in, or intervening in, any political campaign on behalf of (or in opposition to) any candidate for elective public office.”

Moreover, the prohibition applies to a wide range of activities beyond explicitly urging people to vote for or against certain candidates. It applies to any “activities that may be beneficial or detrimental to any particular candidate” (FS-2004-14). A 501(c)(3) organization violates the ban when there is “some reasonably overt indication in [its] communications … that the organization supports or opposes a particular candidate (or slate of candidates) in an election” (2002 CPE Text5, p 345). This occurs when the content or structure of the publication evidences a bias or preference with respect to the views of any candidate or group of candidates (Revenue Ruling 78-248; Private Letter Ruling 199925051).

For example, in Branch Ministries v. Rossotti (D.D.C. 1999), the District Court upheld the IRS’s determination that a church had intervened in a campaign by placing an ad that suggested that Bill Clinton’s proposed policies were contrary to “God’s law,” and that concluded with “How then can we vote for Bill Clinton?” The takeaway here is that any statement, rhetorical or otherwise, that induces the reader to vote a certain way is expressly forbidden to charitable organizations like 48 Hills.

Redmond may try to claim that he is solely performing the service of educating his readership. This is a common enough defense that the IRS has given guidance on it as well:

…certain voter education activities (including presenting public forums and publishing voter education guides) conducted in a non-partisan manner do not constitute prohibited political campaign activity. In addition, other activities intended to encourage people to participate in the electoral process, such as voter registration and get-out-the-vote drives, would not be prohibited political campaign activity if conducted in a non-partisan manner.

On the other hand, voter education or registration activities with evidence of bias that (a) would favor one candidate over another; (b) oppose a candidate in some manner; or (c) have the effect of favoring a candidate or group of candidates, will constitute prohibited participation or intervention.

There is no excuse for a 501(c)(3) publisher to say that it is simply covering current events, when it is in fact expressing a highly partisan bias. The Treasury makes it clear that educating the public doesn’t get you a free pass when it comes to electioneering: “Educating the public is not inherently inconsistent with the activity of impermissibly intervening in a political campaign” (Technical Advice Memorandum 8936002). 48 Hills is not treading in a gray area. It is far, far over the allowable line for charitable entities, which I will show in more detail.

Specific Electioneering Violations

In November 2016, San Francisco held elections for five members of its Board of Supervisors, and for the State Senator representing the city. 48 Hills consistently ran afoul of the electioneering ban during this election by hugely favoring progressive candidates. It also did so in many other elections, but I’ll focus on this one for simplicity’s sake. For reference, here is the list of candidates in this election by faction:

Position Progressive Candidate Other Candidate(s)
District 1 Supervisor Sandra Lee Fewer Marjan Philhour
District 3 Supervisor Aaron Peskin Various
District 5 Supervisor Dean Preston London Breed
District 7 Supervisor Norman Yee Joel Engardio and Others
District 9 Supervisor Hilary Ronen Josh Arce
District 11 Supervisor Kimberly Alvarenga Ahsha Safai
State Senate Supervisor Jane Kim Supervisor Scott Wiener

In Forum: What the Nov. elections mean (October 2016), Redmond writes “Control of the Board of Supes is at stake – and that means the policy direction of the city. If the mayor’s allies wind up back in charge, it will be two difficult years.” “Mayor’s allies” refers here to the candidates running against his favored progressive candidates. He then goes on to say “If you want help sorting all of this out (beyond, of course, going to the Bay Guardian endorsements)…” which is an explicit and direct link to a slate endorsing those same progressive candidates. This is a violation of previously mentioned IRS guidance to not endorse a particular candidate. The link to the Bay Guardian slate is even more specifically and egregiously a violation of prohibitions on “Linking to web pages containing materials favoring or opposing a candidate for public office” (Revenue Ruling 2007-41). It also bears mentioning that the Bay Guardian is a 501(c)(4) also owned by Tim Redmond, and both it and 48 Hills are headquartered at his home in San Francisco.

In The Agenda: Rose Pak, the devastation of the Eastern Neighborhoods (September 2016), Redmond denigrates the endorsements of SF newspaper The Chronicle:

It’s a good thing nobody pays attention to the Chronicle’s endorsements, since the paper’s choices for the Board of Supes races are just embarrassing. Except for Aaron Peskin, who got the nod in part because he is running essentially unopposed, the lineup completely excludes the progressives, even when the moderate candidate is really weak. Ahsha Safai? Nato Green has an excellent piece noting that he has “a distinguished record of not doing much.” (Except helping screw up the Housing Authority):

Josh Arce? Joel Engardio?

Oh well. As I said, nobody listens to the Chron anyway.

This is a very clear disapproval of candidates Safai, Arce, and Engardio, who ran against progressive candidates. Again, this is in direct violation of the very simple IRS rule that you not express an opinion on specific candidates. It is worth noting that unlike 48 Hills, The Chronicle is not a 501(c)(3) and does not violate the law by publishing candidate endorsements.

48 Hills also uses a host of code words to signal disapproval for candidates. In The story Ahsha Safai doesn’t tell in his campaign for supervisor, Redmond describes Safai as a “real-estate speculator, house flipper.” In a piece entitled Wiener featured guest at banquet of landlord activist who opposes transgender rights, he labels the sponsor of an event then-Supervisor Wiener attended as “one of the more radical landlord-rights advocates in the city.” These code words serve the transparent purpose of indicating disapproval for the associated candidates in their elections through disdain for the real-estate industry. This messaging via implicit understanding of code words is, again, expressly forbidden (2002 CPE Text, p. 345).

I have attached, in a companion binder of evidence, many more violations that also span other elections, such as the election for members of the San Francisco Democratic Committee Central Committee in June 2016. In reading through 48 Hills’ long publication history, one cannot avoid the impression that it is an official campaign mouthpiece of specific “progressive” candidates in San Francisco. It regularly defends them during their campaigns, levels charges against their opponents, and communicates the “correct” electoral outcome to its readers.


I don’t doubt that Tim Redmond and the staff at 48 Hills believe they are advocating in good faith, nor do I think they shouldn’t be allowed to write the things they write. The populace is best served by open discourse. Though I strongly disagree with many things that 48 Hills has published, I find, in fact, that it is useful to have the opposition’s ideology laid out so plainly.

However, I can’t stand for rank hypocrisy. 48 Hills has written many times about how its political opponents are financially corrupt. In The Panama Papers and SF’s housing crisis, Redmond asserts “But it would be completely insane to believe that all of that new housing that the mayor is praising is being built without some of this illegal, secretive cash.” This publication has avoided most of its tax obligation while failing to follow even basic guidelines about how not to commit electioneering. The irony of it speculating on the financial corruption of others is almost palpable.

Requested Action

The IRS should immediately revoke the San Francisco Progressive Media Center’s 501(c)(3) status. Per Internal Revenue Code section 4955, it should also impose a 10% tax on the entity for all campaign-related expenditures (including staff salary for all relevant articles).


Vincent Woo