FORT WAYNE, Ind. (WANE) – It happened as a jury was being selected.

For years, Henry E. Underwood wrote letters to a federal judge and filed motions that ultimately went nowhere.

For years, he tried to find a loophole in the law, spouting what a judge would call “frivolous sovereign-citizen” type claims where he argued anything passed by congress didn’t apply to him under the constitution.

He represented himself in legal matters until recently, requesting a public defender. Then he said his attorney was ineffective. He even tried to get married while in jail at one point – all presumably attempts to delay proceedings.

Henry E. Underwood

But with a trial set to begin Monday and potential jurors waiting to be questioned before hearing evidence in a U.S. District Courtroom that Underwood committed racketeering and murder, that he tried to kill a federal witness set to testify in a separate case, the 29-year-old had a change of heart.

And he pleaded guilty.

Thus, a years-long interplay between a man once accused of killing a North Side High School football coach and a legal system he taxed with incessant filings despite orders to stop might be coming to a close.

Underwood pleaded guilty to one count of trying to kill a federal witness Monday, accepting a plea deal from U.S. attorneys who agreed to drop racketeering, murder and gun charges levied against him.

In return, Underwood is facing no more than 30 years in prison, according to court records.

Underwood and a man named Tyshon Powell were both charged with racketeering and murder back in 2020, accused of trying to kill a witness in another case.

Few details of that case or how Underwood and Powell tried to kill the person have been released, other than they were armed with guns at the time.

Powell eventually pleaded guilty last year to one count of trying to kill a federal witness as part of a deal ultimately the same as the one handed to Underwood.

Underwood, meanwhile, represented himself during a separate trial on a count of being a violent felon in possession of a handgun.

In that case, Fort Wayne police were investigating a vandalism-by-gunfire complaint in which someone shot into a house in December 2019. Shortly after the shooting, police stopped a vehicle and found Underwood inside along with a 9-milimeter pistol loaded with live ammunition and an extended magazine, according to court documents.

In a video posted to social media earlier that day, Underwood – then a felon – could be seen handling the firearm. Federal prosecutors also accused him of being the leader of a mob that went to the home to instigate a fight with someone inside before bullets were fired in the home.

Underwood’s attempts at being a lawyer during his three-day trial in U.S. District Court ended in a guilty verdict.

Afterward, he requested a public defender to represent him for his sentencing – he eventually received 8 1/2 years in prison – as well as the racketeering and murder case filed against him.

Several times, in letters to U.S. District Court Judge Holly Brady, he claimed his counsel, a decades-long veteran of law, was ineffective.

“Since his indictment, the record has no shortage of letters from Underwood on an assortment of matters ranging from his expression of sovereign citizen platitudes to the filing of writs and notices, to his dissatisfaction with counsel,” Brady wrote in one of her final orders before trial, shooting down Underwood’s last attempt to get a new lawyer and delay proceedings.

“By December 2022, Underwood discovered that lawyering isn’t as easy as television makes it look and asked the court to appoint him counsel,” Brady wrote, quoting Underwood in her order as saying to her at one point that “this pro se stuff is kinda’ difficult.”

After repeated complaints about his lawyer, Brady scheduled a hearing to address the issues between Underwood and his attorney.

Underwood’s concerns, though, were “thwarted by his belligerence, his frequent ranting, and his repeated statements during the hearing that there was ‘no way no how’ he was going to trial with (the attorney). But that decision, to Underwood’s dismay, is not his to make,” Brady wrote in court documents.

With Monday’s decision to accept a plea agreement from prosecutors, Underwood is now set to be sentenced in September on the attempting to kill a witness charge.

Whatever he receives, it will likely run consecutive to the 8 1/2 years he was given previously for being a violent felon in possession of a handgun.

Back in 2017, Underwood avoided a murder conviction connected to the killing of 36-year-old Terrance Miles.

Miles, an assistant football coach at North Side, was gunned down near a parking lot entrance to East Central Towers Apartments, along East Washington Boulevard. Allen County prosecutors eventually charged Underwood and another man in the killing.

That man, identified as Jaevin Bowie, said he was an accomplice in the killing and saw Underwood pull the trigger.

During Underwood’s trial, though, Bowie changed his story several times and a jury found Underwood not guilty in the killing.