Tech billionaire Jack Dorsey has endorsed Kentucky Congressman Thomas Massie for president, a move that highlights growing friction within the Republican Party. The endorsement from the Twitter co-founder immediately sparked significant online discussion and drew a sharp response from former President Donald Trump .
Dorsey expressed his support for Massie on the social media platform X. His post quickly gained traction, receiving tens of thousands of likes and a mix of supportive and critical comments. Some users celebrated the endorsement, while others questioned Dorsey's record on free speech during his time leading Twitter .
In response, Massie thanked Dorsey for the support but indicated he is unlikely to launch a presidential campaign. He stated he would prefer to see more independent voices in Congress who are not beholden to party leadership. Massie said his goal is to encourage a Congress where members do not always just do what their party tells them to do .
The public endorsement has intensified the existing political conflict between Massie and Trump. Following Dorsey's post, Trump used his Truth Social platform to endorse a primary challenger against Massie, a candidate named Ed Gallrein. Trump called Massie a "lightweight" and a "totally ineffective LOSER" . He praised Gallrein, a former Navy SEAL, and urged him to enter the race. Massie quickly fired back, labeling Gallrein a "failed candidate and establishment hack" . This is part of a broader effort by Trump's political machine to oust Massie, with operatives having established a super PAC called MAGA KY with millions of dollars aimed at defeating the congressman .
Thomas Massie is a unique figure in Washington. An MIT-trained engineer, he earned bachelor's and master's degrees from the prestigious institution . While at MIT, he co-invented haptic interface technology, which allows users to interact with digital objects through touch. He used this innovation to co-found SensAble Technologies, a startup that secured millions in venture funding, created dozens of jobs, and obtained numerous patents . After his tech career, he returned to Kentucky, where he and his wife built an off-the-grid home on a cattle farm they operate .
Massie entered politics as Lewis County Judge Executive before winning a special election to Congress in 2012 . In the House of Representatives, he has built a reputation as a staunch libertarian-leaning Republican. He is known for his consistent votes against major spending bills and bipartisan agreements he views as fiscally irresponsible or an overreach of federal power . This independent streak has often put him at odds with his own party's leadership, including Trump. Massie has broken with Trump on key votes, including a major domestic agenda bill and a military strike on Iran, which Massie argued was unconstitutional . His voting record is so defined by opposition that he was once nicknamed "Mr. No" for frequently being one of the few, or even the sole, representative to vote against legislation .
Jack Dorsey is one of the most prominent figures in the technology industry. He is best known as the co-founder and former CEO of Twitter, now known as X, and as the founder and CEO of the financial services company Block, formerly Square . His political donations have historically leaned Democratic, with contributions to candidates like Tulsi Gabbard and Andrew Yang, and he has supported progressive causes such as a universal basic income . However, his political philosophy has proven difficult to categorize. In recent years, he has expressed strong support for free speech online and for cryptocurrency, and he was reportedly supportive of Elon Musk's takeover of Twitter . His endorsement of Massie, a libertarian conservative, is his latest unexpected political move, having also recently endorsed Robert F. Kennedy Jr.'s presidential bid .
Massie's political strength lies in his deep connection with his northern Kentucky district, which political observers describe as having a uniquely independent and libertarian-leaning character . The district encompasses a mix of Cincinnati suburbs and rural Appalachian counties, creating an electorate that values limited government and individual liberty. This has allowed Massie to build a powerful base of "Liberty Republicans" who are loyal to his principles, even when he defies a popular Republican president . He has actively nurtured this movement by fundraising and campaigning for like-minded local candidates .
Massie has shown confidence in his ability to withstand Trump's political attacks. He claims his online fundraising model is "impervious" to the donor blacklist that often follows a Trump condemnation. He pointed to several strong fundraising hauls after being criticized by Trump, including one period where he raised nearly $370,000 . His confidence is also bolstered by support from other tech leaders. Elon Musk has also posted on X that he would be supporting Massie's campaign, though Massie noted they have never met in person .
The clash highlights a significant ideological divide within the conservative movement. Massie represents a libertarian wing that prioritizes strict constitutional limits on government power, fiscal restraint, and a non-interventionist foreign policy. This sometimes conflicts with the populist and nationalist agenda that Trump leads . As one political analyst noted, voters in Massie's district love Trump's agenda but are often more loyal to the principle of limited government that Massie champions .
The situation remains fluid. While Massie has said a presidential run is doubtful, the high-profile endorsement from Dorsey ensures his voice and his conflicts with Trump will remain in the national spotlight. The stage is set for a contentious primary battle in Kentucky's 4th District, with Trump's political machine and millions of dollars arrayed against a congressman who believes his deep local roots and firm principles make him unbeatable .