Jack Dorsey endorsed Kentucky congressman Thomas Massie for president — a surprise nod that lit up social media and showed the billionaire’s growing embrace of anti-establishment politics.
The Twitter co-founder and Block CEO posted a six-word message on X on Sunday night: “@RepThomasMassie for president.”
The post racked up millions of views within hours and drew a wave of reactions from across the political spectrum — from libertarian fans to Trump loyalists to progressives puzzled by Dorsey’s latest move.
Massie, the Republican lawmaker known for his maverick streak and frequent clashes with party leadership, quickly acknowledged the endorsement.
“I doubt I’ll run for POTUS, but I appreciate the support @jack,” Massie wrote in reply.
“I’d be happy if we could just get 4 or 5 more voices in Congress who don’t always just do what their party tells them.”
The brief exchange instantly became one of the day’s most talked-about political moments, spotlighting an unlikely alliance between the Silicon Valley billionaire and the rural Kentucky engineer-turned-lawmaker.
Massie, 54, represents Kentucky’s 4th Congressional District and has earned a reputation as one of Washington’s most independent figures.
A graduate of the Massachusetts Institute of Technology with degrees in electrical and mechanical engineering, he co-founded SensAble Technologies, a startup that developed haptic devices allowing users to “feel” virtual objects through touch.
After returning to his home state, Massie built an off-grid home powered by renewable energy and launched his political career locally, eventually winning a special election to Congress in 2012.
Since then, he has served on the House Transportation and Judiciary committees, often voting against major spending packages and bipartisan bills he views as unconstitutional or fiscally reckless.
His habit of breaking with his own party — and with President Donald Trump — has earned him both admiration and isolation inside the GOP caucus.
Dorsey, 48, has followed a similar path of independence in the tech world.
After co-founding Twitter in 2006 and stepping down as CEO in 2021, he has championed decentralization, free speech and cryptocurrency as antidotes to both government and corporate control.
In recent years, he’s backed a string of anti-establishment candidates across the political spectrum — including Democrat-turned-independent Robert F. Kennedy Jr.; former Democratic hopeful Andrew Yang; and current national intelligence chief Tulsi Gabbard.
His latest endorsement of Massie, a Republican, highlights his increasing alignment with libertarian and independent voices.
Dorsey has repeatedly expressed skepticism toward centralized power structures, whether in Silicon Valley or Washington.
He has invested heavily in Bitcoin and in Bluesky, a decentralized social media project he describes as a way to “return control to users.”
Dorsey’s post endorsing Massie for president drew over 3 million views by Monday morning.
This story originally appeared on NYPost
