The Trump Presidency Timeline

Donald Trump rolled out of his Truth Social bunker last night to endorse former Fox News host and David Cameron sidekick Steve Hilton for California governor, because why wouldn’t the largest state in the country be run by a guy whose main qualification is once yelling at liberals on cable news?

Trump promised that “as President, I will help him” and that “with Federal help, and a Great Governor, like Steve Hilton, California can be better than ever before!” Subtle as a brick: elect my guy and maybe the federal government will stop treating the country’s biggest economy like an enemy state. Elect anyone else and enjoy four more years of disaster tourism from Mar-a-Lago.

The GOP field is basically Hilton vs. Riverside County Sheriff Chad Bianco, while eight Democrats politely reenact the Spider-Man pointing meme in California’s jungle primary. Polls show no clear frontrunner and a non-trivial chance of a two-Republican general, which is why the state party chair is begging low-polling Democrats to stop cosplaying as viable candidates. Meanwhile, Hilton is out here promising tax cuts, homeownership, and better test scores, as if the main structural barrier to California’s future was not enough Steve Hilton in it.

So the Trump machine is now explicitly offering a loyalty rewards program for governors: say the right things on TV, get the presidential seal of approval and a vague promise of extra federal goodies. It’s not quite handing out ambassadorships to donors, but it’s the same basic model—just with more wildfire risk and a much bigger GDP.

Under Donald "man of the people" Trump, billionaire fortunes hit all-time highs while the federal minimum wage stayed frozen at $7.25, like a museum exhibit from a time when groceries didn’t cost your firstborn. Oxfam reports that in the year after Trump’s re-election, billionaire wealth grew three times faster than in the previous five years, which is what happens when you pass tax laws written like a love letter to private jets and stock buybacks.

Out in the real world, people like Karen Sanchez are spending their free time at breweries asking strangers if they’d like to mildly inconvenience Elon Musk’s net worth. California’s pushing a one-time 5% wealth tax on its 200+ billionaires to patch the holes blown in hospital and education funding, while states like Massachusetts and Minnesota are already using millionaire taxes to do radical things such as feeding kids and fixing roads. At the federal level, Bernie Sanders and Ro Khanna have the audacity to propose that billionaires pay an annual 5% wealth tax, which in Trump’s America ranks somewhere between arson and treason.

Polls show about 70% of Americans think the system is rigged for corporations and the wealthy, possibly because the system is very obviously rigged for corporations and the wealthy. After Trump’s 2017 and 2025 tax cuts shoveled money to the top, CEOs of the five biggest US companies are averaging $52 million a year while the people who actually keep the country functioning are told to be grateful for "opportunity" and maybe some pizza in the break room. So yes, billionaire fortunes are soaring, and so is the movement to finally send them a tax bill that isn’t written in crayon by their lobbyists.

The Department of Homeland Security shuts down, TSA officers are working for free like it's an unpaid internship from hell, airports are collapsing into pure chaos – and Clear Secure’s stock is up 57%. Truly, the free market has spoken: why fund a functioning government when you can just pay $209 a year to skip past the peasants in line while the people actually doing security work can’t afford gas?

Clear’s app downloads jumped 625% in a single Sunday because nothing motivates Americans like the chance to buy their way out of a crisis the government created. TSA workers are unpaid, lines are "sprawling", and Clear helpfully deploys 3,500 "ambassadors" to manage the mess and toss out $200,000 in gas and grocery cards – a tidy PR write-off to paper over the fact that the shutdown that’s wrecking people’s lives is a growth opportunity on their earnings call.

And as the public system crumbles, TSA is partnering with Clear to roll out biometric e-gates that don’t need a human operator. So the government underpays and demoralizes its workforce, then quietly tests out replacing them with retina scanners run by a private company whose business model depends on permanent dysfunction at the checkpoints. What a coincidence. American travelers “deserve better,” Clear’s executive says – and by “better” he clearly means a future where security is two-tiered: premium face-scan fast lane for those who can afford it, and a six-hour line for everyone else stuck inside the world’s most profitable shutdown.

Georgia’s GOP primary for governor was already a MAGA-themed demolition derby, and then billionaire health care executive Rick Jackson showed up, dumped a promised $50 million on the track, and asked voters if they’d like a second helping of 2016 Trump with slightly worse branding.

Jackson has spent nearly $16 million in a month introducing himself as a "straight-talking, Trump-supporting self-made outsider" who "doesn’t owe anybody anything" — a fun line from a man attempting to purchase the governor’s mansion with couch-cushion change. He launched his campaign by descending in a glass elevator to evoke Trump’s golden escalator entrance, because if you’re going to cosplay as an authoritarian-adjacent cult leader, you might as well commit to the bit.

While Trump has already endorsed Lt. Gov. Burt Jones, Jackson is running a delicate little fanboy operation: he’s not touching Jones, but he is airing an ad calling Brad Raffensperger — the Republican who refused Trump’s request to help steal Georgia in 2020 — a "Judas" who "turned on his own kind." That spot conveniently aired in D.C. and West Palm Beach media markets, just in case a certain Florida resident needed his ego stroked between indictments.

The result: a billionaire oligarch trying to buy a governorship, a Trump-endorsed candidate, the state’s top law enforcement officer, and the secretary of state who once defended basic democracy all clawing for the same MAGA base. Georgia Republicans aren’t just running a primary; they’re holding auditions for who can best punish the guy who wouldn’t help Trump overturn an election — and who can spend the most to do it.

North Carolina Democrats are headed to the polls to answer a simple question: what kind of opposition to President Trump’s second term would America’s billionaire class prefer? In the state’s 4th District, Rep. Valerie Foushee — the safe, well-connected incumbent with "good committee assignments" and a reputation for bringing home federal dollars — is being challenged by Durham County Commissioner Nida Allam, a Sanders-aligned progressive who thinks maybe ICE raids and unconditional support for Israel’s Gaza war aren’t actually the height of moral leadership.

This would be a normal intra-party ideological fight if it weren’t also a proxy war for every Super PAC with a checkbook and a god complex. Allam is denouncing "billionaire-funded Super PACs like crypto and AIPAC" trying to buy democracy, while simultaneously benefitting from outside progressive spending herself — because in Trump’s America, even the people running against oligarchic capture have to rent some oligarchic capture just to get on the field. Meanwhile, establishment Democrats rally around Foushee on the grounds that she already knows how to navigate the burning building that is Congress, so why waste time training a new firefighter?

The district is so blue that whoever wins the primary basically gets a congressional seat pre-installed, no assembly required. So the real contest isn’t Democrats vs. Republicans; it’s whether the party’s response to Trump’s authoritarian cosplay will be a louder, younger left flank or a smoother, more senior version of the status quo — all refereed by the same national donors who underwrite the system that made Trump possible in the first place. American democracy remains a vibrant marketplace of ideas, provided your ideas come with a robust fundraising operation.

Pollsters have discovered a new scientific benchmark for American politics: Donald Trump is now less popular than spiders and ants, but still doing better than wasps and mosquitoes. So congratulations to the president – he’s officially performing somewhere between household pest and bloodsucking biohazard. Naturally, this historically unpopular guy with a 61% disapproval rating is insisting on Truth Social that these are the "highest poll numbers" he’s ever had, because reality is for losers and non-felons.

The 2026 midterms loom, and Trump is reportedly telling Republicans behind closed doors that if they lose the House, Democrats will "find a reason to impeach" him. That’s not paranoia so much as a confession with stage fright. A Democratic House could slow-roll his agenda and actually investigate all that "government overreach" the article politely tiptoes around, which is why he’s suddenly discovered the concept of consequences.

Of course, unlike ants, Trump has a few advantages – namely, a firehose of billionaire cash. The RNC is sitting on $95m, Democrats are rummaging in the couch cushions with $14m and some IOUs, and Trump’s Maga Inc super PAC is parked on about $304m like a particularly litigious dragon. Overall, Republicans have over $600m ready to burn on the midterms, while Democrats limp in under $200m, and outside groups are projected to drop another $5bn. It’s not an election so much as a hostile takeover funded by 100 very rich families who spent $2.6bn in 2024 to make sure the rest of us keep arguing about bugs while they buy the government.

So as the midterms approach, America faces a stark choice: let a deeply unpopular president backed by a mountain of oligarch money keep rewriting the rules, or see if voters like democracy more than they dislike spiders. Polling suggests ants, at least, still have a better reputation than Congress.

Anthropic has decided the best way to make sure AI "serves the public good" is to shovel $20 million into a political group to influence who writes the laws about AI. The money goes to Public First Action, a nice, wholesome outfit whose main mission is to stop the federal government from overriding state AI regulations — including that December Trump executive order designed to kneecap pesky state-level rules that might inconvenience his tech buddies.

One of the lucky beneficiaries: Republican Marsha Blackburn, now running for Tennessee governor, who bravely fought against Congress trying to stop states from passing their own AI laws. So yes, we have an AI company bankrolling a Republican politician to resist federal preemption pushed by Trump, all so the "public good" can be lovingly curated by whichever donor has the biggest checkbook this quarter.

Across the field, Leading the Future — backed by OpenAI president Greg Brockman and VC hype priest Marc Andreessen — has already hoovered up $125 million to fight stricter AI regulation. So the midterms are shaping up to be a delightful little experiment in algorithmic self-governance, where the people get to choose between Team Slightly-Regulated AI and Team Please-Do-Not-Regulate-My-Stock-Options, while Trump’s executive orders loom in the background like a half-finished Terms of Service written in crayon.

The result: a political system where the most advanced AI labs on Earth are locked in a spending war to decide how lightly they themselves should be policed. Democracy, in its final form: not one person, one vote, but one billionaire, one PAC, one regulatory capture strategy.

The Trump administration has discovered that ending a full-scale European war is just like closing on a casino in Atlantic City: you send a property developer and your son-in-law to Davos and Moscow, declare it's all down to "one issue," and hope nobody notices that the "issue" is carving up another country's territory. Enter Steve Witkoff, Trump donor and real-estate pal turned Ukraine envoy, confidently announcing that peace in Europe now hinges on a single, unnamed sticking point — which, purely by coincidence, appears to be the future status of Ukraine's industrial heartland in Donbas. Because nothing says rules-based international order like letting the guy who usually negotiates mall leases decide how much of your country you get to keep.

While Volodymyr Zelensky rides an overnight train out of a half-frozen Kyiv — where Russian strikes have knocked out heat, water, and power in the dead of winter — Trump is in Davos pitching a 20-point peace plan that is "90% ready," just like every infrastructure week. The "deal" on the table involves demilitarising part of Donbas into a "free economic zone" if Russia plays nice, plus a big question mark over who controls Europe's largest nuclear plant at Zaporizhzhia. Meanwhile, Trump publicly muses that Putin is "ready to make a deal" but Zelensky is "less ready," which is a polite way of saying the guy whose cities are being bombed is not thrilled with the US president and his in-laws workshopping Ukraine's surrender terms with the Kremlin.

Back in Moscow, Dmitry Peskov says talks will continue on the "Ukrainian issue and other related topics," which is diplomatic code for "we like where this is going." Putin hasn't yet decided whether to grace Trump's absurd "Board of Peace on Gaza" with his presence, but the mere fact that this is a sentence anyone has to write tells you everything about the clown car running US foreign policy. Zelensky is still hoping to sign security and economic guarantees with Trump in Davos, but admits there's "one mile left" to go — presumably the same mile between "sovereign ally" and "chip in a Trump-branded global deal so Jared can claim he solved war." In other words, Ukraine bleeds, Europe panics, and America’s diplomacy is being run like a family side hustle.