FORT WAYNE, Ind. (WANE) – A Fort Wayne man once charged in the killing of a North Side High School football coach received an 8 1/2- year prison sentence for possessing a firearm while a felon earlier this week.

The legal issues facing 29-year-old Henry E. Underwood do not end there, however, since he is scheduled to stand trial for murder and racketeering charges in connection to a case where he’s accused of trying to kill or intimidate a witness set to testify in another matter, according to court documents.

A U.S. District Court judge, who has dealt with repetitive motions and attempts by Underwood to either stall the court cases against him or fish for loopholes to get his charges dismissed, sentenced Underwood to 102 months in prison on the gun crime Tuesday.

Henry Underwood

In that case, 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 represented himself in the case and a jury found him guilty after a three-day trial in September.

He also largely represented himself while a murder and racketeering case against him wound through the legal system.

In that case, Underwood and a man identified as Tyshon Powell are accused of trying to kill an unidentified person set to testify in a legal matter sometime between May 2018 and June 2018, according to court documents.

Powell has already pleaded guilty to his role in that case and Underwood’s trial is scheduled for later this year.

In both cases, Underwood filed motion after motion, to the extent the federal judge overseeing the proceedings had to put a halt to his attempts at having the charges dismissed on flimsy grounds.

“Nevertheless, he continues to make frivolous sovereign-citizen type filings and take up the Court’s time with repetitive motions challenging the charges against him,” wrote Judge Holly Brady in one opinion. “Let the Court make this absolutely clear to the Defendant: a generalized assertion that all laws passed by Congress are null and void under the Constitution is not a get out of jail free card in a Monopoly game.”

“There is no genie in a bottle that, once a motion is filed three times, will release the Defendant from the custody of the United States Marshal’s Service,” Brady continued in her order.

Previously, Underwood was acquitted in the 2017 killing of Terrance Miles, an active youth mentor and coach in the area who was gunned down one morning near a parking lot entrance to East Central Towers Apartments.

A key witness in the trial for that killing changed his story several times, ultimately leading to Underwood’s acquittal.

After being found guilty of the gun crime in September, Underwood finally asked to be represented by a public defender for his sentencing and for the remainder of the racketeering and murder case.

Still, he made one more motion on his behalf.

He asked in a letter to the court if he could get married to his girlfriend while incarcerated, according to court documents. The judge struck it from the record.

Underwood’s request for an attorney may have been his own undoing when it came to filing excessive motions.

Under the court’s rules, only someone representing a defendant can file motions.