Trump's 'secretary of retribution' turns against president over major 'betrayal'
Ivan Raiklin while being approached by Raw Story reporters outside Fiserv Forum at the Republican National Convention. Jordan Green/Raw Story
May 19, 2026
Ivan Raiklin, the far-right operative who built his profile as a self-styled "Secretary of Retribution" tasked with going after Donald Trump's enemies, has spent the past several days using his X account to attack the president himself.
Raiklin, a former Green Beret and Army Reserve lieutenant colonel turned constitutional lawyer, emerged as a fixture of the post-2020 election denial movement and was a central figure in efforts to overturn Joe Biden's victory. In the years since, Raiklin has rebranded himself as the self-appointed "Secretary of Retribution," compiling a "Deep State Target List" of more than 350 federal officials, journalists and lawmakers he has vowed to pursue once Trump returned to power.
In a post on Monday, May 19, Raiklin declared bluntly: "Trump has betrayed Massie and KY-04," referring to the president's intervention against Rep. Thomas Massie in the Kentucky Republican primary. Massie, a longtime conservative firebrand, has been targeted by Trump and his allies after voting against the president's signature spending bill and pushing for the release of files related to convicted sex trafficker Jeffrey Epstein.
The day before, Raiklin warned his more than 250,000 followers that "the coalition that got Trump elected in 2024 is breaking ranks to support Massie over Israel, errr Trump." The post nodded to a growing strain in the MAGA base, where parts of the movement have soured on Trump over his administration's posture toward Israel and his moves against Massie.
A day earlier still, Raiklin escalated, referring sarcastically to the president as "Israeli President, Donald Trump" in posts criticizing Defense Secretary Pete Hegseth's appearances campaigning for Massie's primary opponent, Ed Gallrein.
The defection is notable because Raiklin is no peripheral figure. He spent the 2024 campaign cycle compiling what he called a "Deep State Target List," urging Republican state lawmakers to "hand their states' electors to Trump," and recruiting "constitutional sheriffs" to take action against perceived federal enemies. He has been profiled by Raw Story, as well as by the Atlantic, the New Republic, and the Daily Beast, as one of the most aggressive voices in the post-2020 MAGA universe.
That an enforcer of Trump's so-called "retribution" agenda is now publicly accusing the president of betrayal points to a possibility that the reported polling has hinted to for weeks: the coalition is cracking from the inside.