Dave Regan's union enters final four weeks of California billionaire-tax campaign

Four weeks from Election Day, the union campaign behind California's Proposition 40 is in its closing stretch, and the measure — a one-time tax on billionaires that the coverage describes as the first of its kind in any state — has handed a planning conversation that has been abstract all year an actual deadline.

Dave Regan, who heads the healthcare-workers union leading the ballot effort, frames the levy as the only way to cover roughly $100 billion in federal healthcare funding that he says California will lose over the coming years following cuts made under the Trump administration, and he told Bloomberg that he knows the campaign is the underdog but is not stopping regardless of the result, describing Proposition 40 as a potential springboard for wealth-tax campaigns across the country. The union has been mobilizing members statewide and enlisted Senator Bernie Sanders as an ally.

The opposition is broad for an initiative with organized labor behind it: Governor Gavin Newsom and Xavier Becerra, described in the coverage as Newsom's likely successor, have come out against the measure, as have business groups and unions, with opponents arguing that a one-time tax on wealth is poorly designed, unnecessary, and likely to drive wealthy residents and their tax dollars out of California. Sergey Brin, the Google co-founder, has put more than $100 million into a political influence machine mostly devoted to fighting the tax, with an advertising barrage expected to reach voters across television, social media and the mail in the coming weeks, and is also backing two other ballot measures that the coverage says could undercut the billionaire tax even if it passes, though it does not identify them.

What the coverage establishes matters as much as what it doesn't: the argument that a wealth tax drives out the people who pay it is being made by opponents, at volume and at cost, but the coverage reports the argument without measuring it. An advisor who relays that claim to a California client deciding whether to sell a business or move a trust as an established result is overselling a campaign position.

Ro Khanna, the Silicon Valley congressman who appeared alongside Sanders on stage, is the link between this ballot fight and a planning question this publication examined in August, when his loan-for-shares tax plan, as we described it then, would make the state a residual owner of pledged private shares, an arrangement we said family offices should read closely. That is a different proposition from a levy on net worth: a balance-sheet tax is a figure on a return, while a tax that runs through shares a client has already pledged reaches the collateral itself and, with it, the lending arrangements built on top of it.

On Saturday, Sanders took the stage at San Francisco's Curran Theatre before a crowd the coverage puts at more than 1,600, calling the initiative the most important ballot measure in the country and placing it inside a wider fight over concentrated wealth, with Jane Kim, a candidate for state insurance commissioner, and Khanna joining him.

The coverage leaves open most of what an advisor would ask next—what a one-time tax would attach to, net worth on a given date or something narrower; how it would treat a business that has not sold; when it would take effect; or what would follow a legal challenge—and polls, per the same coverage, show an extremely tight contest. A measure polling that closely, with a four-week runway and an opposition campaign that has not yet spent its advertising budget, is a date on the calendar.

The practical work in the meantime is duller than the politics, but clients holding concentrated positions, waiting on an exit, or sitting on private-fund stakes have reason to get residency facts documented and decisions on gifting and timing onto a calendar before the vote, while nobody knows the answer. If Proposition 40 fails, the documentation is harmless; if it passes, an advisor who started in October is not starting from zero in November.

The wider question the campaign has already answered is whether a state wealth tax is a fringe idea. Regan says he has made the issue inevitable and intends to keep organizing whatever the count, and a proposal that draws a sitting senator to a San Francisco theater, fills it with more than 1,600 people, and attracts more than $100 million in opposition spending from a single billionaire is being treated by both sides as consequential; whether that travels beyond California is what the next four weeks test.

Regan has said he keeps going either way, and the advertising the union expects to be carpet-bombed with is still ahead of voters, as are Brin's two other ballot measures, which the coverage does not identify. The deadline is four weeks away, and the opposition campaign has not yet spent its full budget.