Gig workers get gouged. Here’s how Trump can help — and win swing states too

Donald Trump understands the old maxim that taxation is theft, and to that end he’s proposed some interesting ways to ameliorate the burden on actual working people via aggressive tax relief.

The “no taxes on tips” push is all but done on acclamation at this point — Kamala Harris even signed on — an indication Trump has an instinctive understanding of smart policy. It’s just his latest embrace of thinking that’s out-of-the-box for conservative orthodoxy but consistent with his personal brand.

The former president went two-for-two late last week with his attempts to bring tax relief to actual working people.

“No taxes on overtime! The people who work overtime are among the hardest working citizens in our country,” Trump said. “It’s time for the working man and woman to finally catch a break, and that’s what we’re doing because this is a good one.”

As anyone who has ever clocked an extra shift or three knows, this reprieve will help if it happens.

Yet neglected in these proposals are people who are also “among the hardest working citizens in our country”: the Uber drivers and DoorDashers and professional freelancers who hustle with little relief.

They aren’t subject to overtime, as they lack the protections of salaried employees. Many of them don’t get tips either. Yet they get jobbed out all the same, paying the full freight for their Medicare and Social Security with dollars that keep losing real value. It’s a scenario of diminishing returns, where one crisis can tip someone over the edge into insolvency.

Economic justice is a salient argument for tax relief for the 1099 crowd; perhaps a provisional halving of tax burden or a “freelancer’s credit” that helps those plying their trades outside a corporate umbrella. There are ways to scheme that.

And as with Trump’s other tax proposals, there’s political benefit to this throughout the swing states.

From the metastatically sprawling Atlanta area, to the Carolina metros of Raleigh and Charlotte, to Philly, Pittsburgh, Phoenix, Las Vegas, Minneapolis and Milwaukee beyond, many of these people have been left behind in the increase of artificial intelligence in the workplace and corporate rightsizing, forced into gig work right when the dollar has bled value.

Consequently, the rent is too damn high. So is the cost of everything else. And government, which created the conditions that made the cost of labor cheaper than a living wage, owes gig workers and freelancers the same leg up that every other disadvantaged and economically precarious group gets in our tax code.

Trump’s no-tax-on-overtime plan addresses the injustice of going above and beyond for a company that won’t give that courtesy back. The no-tax-on-tips push likewise was the recognition people reliant on gratuities earn their compensation in a way that imposes a real economic cost.

A tax break for freelancers would accomplish the same end.

It would allow them freedom from making hard decisions about delaying getting health insurance or paying some other necessity because there’s no room in the budget. It would give them some measure of security in an economy that both increasingly relies upon them and deleverages them, even as they absorb the capital costs of their profession.

Trump’s proposal would have disproportionate reach to a group of unlikely voters in the seven battleground states and beyond: gig workers who may not be hearing anything relevant to their economic condition from Kamala Harris but who could hear it from Trump.

Setting the freelancers free makes political sense. It offers Trump yet another opportunity to propose meaningful tax reform. And it creates a potentially significant number of unpollable voters, the kinds of people who otherwise might skip an election, in states where small segments of voters will make the difference in November.