We’re roughly 48 hours away from the first batch of results for the June primary election, a contest that — let’s be real — has been a mixture of the painstakingly boring and suddenly shocking. 

The Power Play team will be covering Tuesday’s election with a live blog, on-the-ground reports from watch parties, and big takeaways that come from the night’s results. (Also, if you’re going to any of those parties, make sure to tip us off to the best gossip you got that night. Email us at [email protected].) 

As you’re settling in this evening after a weekend of anticipation for Tuesday, we wanted to give you a sense of what we’re looking out for come election time. 

Hannah Wiley, deputy politics editor: I’m watching to see whether we get a classic Democrat-versus-Republican November general election with Xavier Becerra versus Steve Hilton, or a Dem-on-Dem war between Becerra and Tom Steyer — a 180-degree turnaround from the doomed Republican lockout that Democrats feared in early spring.

A Democratic slugfest would guarantee a Democratic governor. But it would present another nightmare for the party, which wants to put this primary behind it and cruise to easy victory in November.

All recent polls indicate Becerra will make it out of the primary. The big question is who he will face. 

Call me crazy, but I disagree that a Becerra-Hilton run-off would be a good thing for Dems. Sure, it’s basic math of how well a Trump-backed Republican will fare in deep-blue California, and I’m not arguing that Becerra will lose. But Hilton is charismatic and energetic, traits that aren’t typically used to describe Becerra, Biden’s former Health and Human Services secretary. Hilton has ideas that large voting blocs in California like, such as cutting taxes and reducing government spending, and Becerra is the kind of Sacramento insider that exhausted Californians of all political stripes see as causing the state’s massive problems.

The race will remain interesting post-June 2 if Becerra and Hilton make it to November. And if Steyer somehow squeezes it out of the primary? Now that will be downright entertaining. 

Gabriel Greschler, politics reporter: I know everyone is excited for the governor and congressional races, but what I’m really looking forward to is the outcome of measures C and D, the dueling tax propositions. Yes, taxes are boring. But I think whichever measure passes will give us real insight into how people feel about San Francisco’s political direction, and whether a progressive, populist wave might be on the horizon. It is also a barometer of how people feel about Mayor Daniel Lurie, as well as what shakes out for his candidates in districts 2 (Supervisor Stephen Sherrill) and 4 (Supervisor Alan Wong). 

If Measure C, the business-backed proposition that will lower taxes for some small businesses, is the winner, it will mean a couple of things: Moderate, tech-aligned power still reigns supreme in San Francisco. It would also suggest that people are feeling pretty confident about the city’s post-pandemic recovery, having bought the argument from business advocates that San Francisco is making progress on its comeback. 

• Power Play: Five key questions for November’s general election

But a win by Measure D would be a wake-up call for those watching City Hall’s power dynamics. A victory for the union-backed proposition that will raise taxes on businesses with a high executive-to-worker pay ratio would show that some residents could be turning on the moderate set of policies that have been dominant at City Hall since the early 2020s — and that a progressive resurgence may be in sight. It will also be a triumph for the labor unions as they kick off their battle against Lurie later in June over budget cuts.  

Emily Shugerman, wealth and power reporter: I’m watching to see how tech’s record spending this election cycle pays off for them —  if it pays off at all. If you haven’t been following closely, the historically politics-averse tech sector has decided to play in California’s elections in a big way this year, spurred by a long-running desire to moderate the state and reduce its spending, and more importantly, by a desire to squash the proposed billionaire tax from coming for their pocketbooks (and yachts, and mansions, and …)

The question is not if they can deploy the money — they already have, to the tune of hundreds of millions of dollars. The question is if they can spend it well. (Sources are already grumbling to me about how many political consultants are getting rich off giving the new tech donors terrible advice.) Billionaires like venture capitalist (and Standard chairman) Mike Moritz, Google co-founder Sergey Brin, and Netflix co-founder Reed Hastings really came out swinging for Matt Mahan for governor, which already appears to have been a miss. I’ll also be watching to see how tech-backed candidates like Eric Jones in Napa and Ethan Agarwal in the South Bay do in challenging incumbent Reps. Mike Thompson and Ro Khanna, respectively. 

I’ll also have my eye on the dozen or so state assembly and senate candidates endorsed by California Leads and Grow California. Both are tech-funded PACs — California Leads by Meta and Google, Grow California by Ripple co-founder Chris Larsen — but they seem to be running a more traditional political playbook: endorsing existing candidates with real grassroots support. If many of their candidates win on Tuesday, it might be a signal to the rest of the tech industry that they don’t need to disrupt the usual campaign playbook, they just need to fund it.

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Han Li, politics reporter: I’ll be covering the Sunset drama on Election Day. It’s been quite a journey watching the neighborhood get fired up and torn apart over Prop. K, the recall, and now the heated supervisor race. Luckily for me, the election-night parties for the two frontrunners, incumbent Wong and progressive challenger Natalie Gee, are only a block apart. Ill be at both.

For many in the Chinese community, one of the biggest questions is whether Supervisor Connie Chan can make it into the top two. It would be a testament to the strength of the coalition she aims to build: progressives, westside voters, organized labor, and Chinese American voters — with backing from Nancy Pelosi.

And how can we forget Aaron Peskin? We joke that Proposition B, the term-limit measure, is basically a “Peskin Ban” or a “Purging Peskin” initiative. Either way, I’ll definitely call him that night.

Joe Fitzgerald Rodriguez, politics reporter: I’m fascinated by the progressive congressional duel between Supervisor Chan and former AOC staffer Saikat Chakrabarti. There’s long been a tension between the values of San Francisco’s capital-P “Progressive” camp, a coalition of disparate income and ethnic groups with overlapping goals, and those of national progressives, who are more typically Bernie Sanders, squad-style (opens in new tab) voters. The divide between the two often causes whiplash with newcomers and the less politically engaged. 

I don’t remember seeing such a stark example of locally aligned and nationally aligned progressives going head-to-head, as Chan and Chakrabarti are. How does that split the vote in known progressive precincts? And do supporters of one candidate consolidate behind the other when one drops out, or do they — as I’d expect — peel off in some measure to state Sen. Scott Wiener?

Then there’s the broader temperature check on local progressivism. Look, I’m not pronouncing San Francisco is no longer a progressive city — god knows journalists like to do that every few years (opens in new tab). But a clash of progressive titans may reveal just how strong that coalition still is. I’ll be at Chan’s party on election night, picking progressives’ brains about it.

John Mulholland, managing editor: Steve Hilton, the leading Republican gubernatorial candidate heading into Tuesday’s primary, is often referred to as a “former Fox News host.” If he makes it past the primary, expect far more attention on his 10 years at the heart of UK politics. That includes the little-known fact (in the U.S.) that he became the inspiration for one of the central characters in an acclaimed BBC political satire.

For the uninitiated, watch this clip as the shaven-headed, bespectacled PR guru and radical free thinker Stewart Pearson (the Hilton character) conducts an away-day “Thought Camp (opens in new tab)”  while sitting cross-legged on the floor in a circle and rifling through some “blue-sky thinking” to the bafflement and annoyance of his Secretary of State, wh0, as you can see, is not on board with that kind of thing. 

The Thick of It (created by Armando Iannucci who later created The Veep) ran between 2005 to 2012 and was a brilliant satire of the chaos and dysfunction at the heart of a fictional UK government. Hilton was just one of the political figures of that era lampooned in The Thick of It. As a key adviser to Conservative Party leader and Prime Minister David Cameron from 2005-2012, Hilton established a reputation as an eccentric figure — famously shoeless around No. 10, he cycled to work in (not very nice) shorts and T-shirt, was allergic to bureaucracy, contemptuous of civil servants, and prone to grand visionary ideas that were often hard to translate into actual policy.

When he departed UK politics for a life in the U.S. the BBC’s Political editor remarked, “Gone will be the man who greeted President Obama in his socks and who walked the corridors of power in shorts and a T-shirt.” 

Ian Birrell, one of the UK’s foremost political commentators, noted at the time that: “He is seen as some kind of strange, ultra-liberal hippy adviser, forcing crazy Californian-style ideas on his party. Many politicians view him with hostility … deriding him as ‘the shaven-headed Svengali’ and ‘pint-sized Rasputin’ behind the throne. He even had the ultimate accolade of being satirised as babbling Stewart Pearson in the biting TV satire The Thick Of It.”

The Pearson character clearly inflates Hilton’s radical, outsider energy and fondness for corporate away-days. In one memorable scene the Hilton character trots out a series of nonsense insights including “knowledge is porridge (opens in new tab).” He was also keen on “Let’s architecturialise” and “Time is a leash on the dog of ideas.”

After Hilton departed in 2012 — for California — Lord O’Donnell the retired Cabinet Secretary (the UK’s most senior civil servant) said that Hilton liked to “get everything done tomorrow with a tenth of the people.” He also noted that some of Hilton’s plans were not “actually legal.” 

Former Conservative minister Rory Stewart recalled an anecdote in his memoir when a frenetic high-energy Hilton told him that he wanted to “blow up the Foreign Office” and get rid of all the ambassadors, before he quickly moved on to discussing technology and the European Union and then lay on the floor staring at a map saying: “Fuck me, look how big Scotland is. This is just fucking mad, man.”

Sacramento, you have been warned.

JOE SQUARED: What better way to spend your evening than with two fellas named Joe talking up the June primary results? If that tickles your fancy, then show up June 9 at Manny’s to see Power Play’s very own Joe Fitzgerald Rodriguez and Mission Local columnist Joe Eskenazi break down what Tuesday’s race means for the November general election, and any big surprises or hot takes from the contest. Get your tickets here (opens in new tab).