Jack Dorsey supports Republican Rep. Thomas Massie for president as X

Jack Dorsey has endorsed Kentucky Congressman Thomas Massie for president, a surprise gesture that lit up social media and demonstrated the billionaire’s growing embrace of anti-establishment politics.

The Twitter co-founder and CEO of Block posted a six-word message on X on Sunday evening: “@RepThomasMassie for President.”

The post garnered millions of views within hours, and sparked a wave of reactions from across the political spectrum — from liberal fans to Trump loyalists to progressives baffled by Dorsey’s latest move.

Massie, a Republican lawmaker known for his maverick streak and frequent clashes with party leadership, quickly acknowledged the endorsement.

“I doubt I’ll run for President of the United States, but I appreciate @jack’s support,” Massie wrote in response.

“I would be happy if we could get 4 or 5 more votes in Congress who don’t always do what their party tells them to do.”

The brief exchange instantly became one of the most talked-about political moments of the day, highlighting an unlikely alliance between the Silicon Valley billionaire and the rural Kentucky engineer-turned-legislator.

Massie, 54, represents Kentucky’s 4th Congressional District and has gained a reputation as one of the most independent figures in Washington.

A Graduate of Massachusetts Institute of Technology With degrees in electrical and mechanical engineering, he co-founded SensAble Technologies, a startup that developed haptic devices that allow users to “feel” virtual objects through touch.

After returning to his home state, Massie built an off-grid home powered by renewable energy and began his political career locally, eventually winning a special election for Congress in 2012.

Since then, he has served on the House Transportation and Judiciary committees, often voting against major spending packages and bipartisan bills that he considers unconstitutional or fiscally reckless.

His habit of breaking away from his party — and from President Donald Trump — has earned him admiration and isolation within the GOP caucus.

Dorsey, 48, has followed a similar path to independence in the world of technology.

Having co-founded Twitter in 2006 and stepped down as CEO in 2021, he has championed decentralization, freedom of expression, and cryptocurrencies as an antidote to both government and corporate control.

In recent years, he has supported a series of anti-establishment candidates from across the political spectrum — including Democrat-turned-independent Robert F. Kennedy Jr.; former Democratic candidate Andrew Yang; And the current head of National Intelligence, Tulsi Gabbard.

His recent endorsement of Massie, a Republican, highlights his growing alignment with liberal 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 that he describes as a way to “give control back to users.”

Dorsey’s post endorsing Massie for president had attracted more than 3 million views by Monday morning.