Mr. President, Please Free Caleb Bailey

Stephen Moore
Tue, 27 Jan 2026 15:29:14 -0800
Opinion

"How can the life of such a man / Be in the palm of some fool's hand?" — Bob Dylan, "Hurricane"

You've probably never heard of Caleb Bailey, but he is a political prisoner who has been locked behind bars for nearly eight years; nine more years remain on his sentence.

Anyone who has publicly supported Donald Trump should cringe when hearing the facts of his case.
Updated: Tue Jan 27, 2026

"How can the life of such a man / Be in the palm of some fool's hand?" — Bob Dylan, "Hurricane"

You've probably never heard of Caleb Bailey, but he is a political prisoner who has been locked behind bars for nearly eight years; nine more years remain on his sentence.

Anyone who has publicly supported Donald Trump should cringe when hearing the facts of his case.

In his state of residence, Maryland, violent rapists, armed robbers and kidnappers have received shorter prison sentences. Yet Caleb has never in his life committed a violent act.

Not once.

So why is he in prison serving a term of 16 years and eight months?

Judge for yourself.

In April 2016, Caleb and his father were elected as Trump delegates to the Republican National Committee from Maryland. Maryland is, of course, one of America's most politically liberal and Trump-hostile states.

On May 5, 2016, just seven days after his name appeared in local media for being chosen as a Trump delegate, Caleb's home was raided by a squad of 42(!) heavily armed agents from the Bureau of Alcohol, Tobacco, Firearms and Explosives. They presented a search warrant, then occupied and ransacked his home for more than eight hours.

After conducting their arguably illegal search and seizure that violated Caleb's Fourth Amendment rights, the agents seized and hauled away in three large U-Haul trucks nearly $200,000 worth of Caleb's private property — most of which were items not on the search warrant.

Among the many outrages of this case is that much of Caleb's life savings was never returned to him. Valuable coins that he had collected, for example, mysteriously disappeared.

Caleb was charged with illegal possession of several firearms (he was a gun collector), including 37mm safety flare launchers, which used to be sold over the counter by Walmart and sporting goods stores. None of the guns was ever used in the commission of any crime.

The agents also found in their illegal search several old DVDs that they claimed contained child pornography. Caleb informed the agents that the videos had been sent to him unsolicited in the mail. There was zero evidence that he was a distributor, and an electronics expert agreed that the material was dormant.

For these crimes, Caleb was handcuffed and sent to a maximum-security jail in Baltimore, even though agents on the scene had told Caleb and his father that his offenses were so minor that he deserved to be sent to a "low"-security jail. He was denied bail.

Before his trial, the prosecutors told Caleb's lawyer that they would ask for an outrageous life sentence unless he took a plea bargain. Faced with the harrowing prospect of decades in prison, he took a plea deal.

A typical sentence for illegal gun ownership is two to 10 years. The prosecutors recommended 10 years for EACH infraction.

Again, NONE of these guns was ever used in the commission of crime, because Caleb never committed any crime. Lawyers who have looked into the case say that since Caleb was a first-time offender, the typical punishment for these offenses would have been probation or less than a year in jail — not 16 years.

He's already served almost eight years, so even if you believe every allegation, he has more than served punishment for his crimes. Prison officials describe his behavior while behind bars as "exemplary." He has declared remorse for his actions.

In a letter to President Donald Trump, Tony Covington, a tough-on-crime state's attorney in Maryland, wrote that in his entire career, he has "never offered an opinion or recommendation on the commutation of someone's sentence. I do so now because I believe that justice can best be served by granting Mr. Bailey's (pardon) request."

The Washington Post and others have accused Trump of abusing his pardon powers to gain freedom for his political supporters.

They have the story upside down. In too many of these hundreds of cases, men and women who have been granted clemency were unjustly incarcerated by Trump-hating prosecutors and judges simply BECAUSE they supported Trump. They were tossed In prison for the crime of helping Trump win the election.

Caleb has lost nearly eight of the best years of his life to flim-flam charges. The Trump haters who are supposed to serve justice want him to serve another nine years behind bars.

This case shakes your faith in the American jurisprudence system. It exemplifies the depths of depravity of those suffering from Trump Derangement Syndrome.

Please, Mr. President: Free Caleb Bailey.