Crime

Former Chester County SC Sheriff Alex Underwood reports to federal prison in Kentucky

Former Chester County Sheriff Alex Underwood, right, convicted of crimes in federal court, must report to prison Oct. 14, a federal judge ruled on Oct. 5, 2022.
Former Chester County Sheriff Alex Underwood, right, convicted of crimes in federal court, must report to prison Oct. 14, a federal judge ruled on Oct. 5, 2022. tkimball@heraldonline.com

Alex Underwood is now in federal prison, officials said Friday afternoon.

This comes a decade after he was elected Sheriff of Chester County, S.C. It also marks the end of a career where the sheriff reached high acclaim before falling to criminal convictions.

George Alexander “Alex” Underwood, 59, reported to federal prison at the U.S Penitentiary Big Sandy in Kentucky, according to an emailed statement to The Herald from Benjamin O’Cone, a spokesman for the federal Bureau of Prisons. The prison is in Inez, in eastern Kentucky near the West Virginia border.

Underwood’s lawyers had asked federal officials for Underwood to be placed in a prison outside of South Carolina because of Underwood’s long law enforcement career.

Underwood is appealing his 2021 conviction and 46-month prison sentence on eight felony charges. He had asked for bond so he could remain free during the appeal. But federal judge Joseph Anderson Jr. ordered Underwood to report to prison by Friday.

Former Chester deputy Johnny Ricardo Neal also was in prison as of Friday, according to the Bureau of Prisons. Neal is in a federal prison in Ashland, Ky., prison officials said in a statement to The Herald. Neal also is serving a 46-month sentence.

The convictions

Underwood was convicted on charges of conspiracy to commit wire fraud, federal program theft, falsifying records, and the attempted cover up and unlawful arrest of a Chester County man in 2018, court records show.

The convictions were the result of Underwood misusing federal DUI checkpoint enforcement money that should have gone to deputies, and forcing deputies to work on a man-cave party barn at his home, William Miller, the assistant U.S. Attorney from Washington D.C. who prosecuted Underwood, said in court filings.

When Underwood was sentenced in July, Miller said in court that the sheriff is powerful and a symbol.

“(Underwood) lied, he cheated, and he stole when he got into power,” Miller said in July.

Miller said Underwood was someone who should have stood for the rule of law but instead broke the law repeatedly.

Prosecutors described Underwood as a “crook and a bully.”

Underwood also was convicted of falsely arresting a man after the former sheriff confronted the man who was doing a Facebook Live video. The arrest was covered up with false reports and lies to the FBI, according to court testimony and documents.

Neal and former chief deputy Robert Sprouse, were convicted at the same trial as Underwood in 2021. Sprouse was sentenced to 24 months. He reported to prison in September.

Underwood has continued to maintain his innocence. He said at sentencing that his race was part of the reason he had been targeted by political enemies. Prosecutors denied that claim.

Chester County is a largely rural county between Charlotte and Columbia with around 32,000 people. Chester County’s population is around 40 percent African-American

Underwood’s tenure as sheriff

A former State Law Enforcement Division agent, Underwood, a Democrat, was elected in 2012 and re-elected in 2016 as the county’s first Black sheriff.

Underwood, also is known as “Big A.” Over time, the nickname became a common identity because of his stature. Underwood stands around 6-foot-3, and weighs over 200 pounds.

Underwood’s early tenure was marked by successes in the 2014 arrest of gang members connected to the killing of Chester City Councilman Odell Williams.

Underwood also gained national attention when he brought a Pennsylvania boy to Chester for a hunting trip. That happened after a mixup over an Underwood-sponsored outdoors activity. The boy thought the event was in Chester County, Pa.

After The Herald covered the mixup and Underwood brought the boy to South Carolina, the story was covered as far away as England and Australia.

Underwood appeared in national media for his relationship with the Chester, Pa., boy and for his tough stances on crime, gangs and drugs.

Underwood was selected Sheriff of the Year for South Carolina during his term.

When Underwood ran for re-election in 2016, he sent this statement to The Herald about himself:

“Known to many simply as ‘Big A,’ Underwood is a trusted and well respected law enforcement veteran and legend in his own time.”

Indictment in 2019

But Underwood came under scrutiny in 2019 when the FBI began investigating the claims of Kevin Simpson, the Chester man South Carolina prosecutors said was wrongly arrested.

FBI agents raided Underwood’s sheriff’s office in the Spring of 2019 and on May 7, 2019, federal prosecutors announced a grand jury had indicted Underwood and the two top deputies.

South Carolina Gov. Henry McMaster suspended Underwood from office the same day in May 2019. McMaster appointed Max Dorsey as sheriff.

Underwood ran for re-election in 2020 while suspended and under indictment, but was defeated by Dorsey, a Republican.

Underwood, former Chester supervisor in prison same day

Underwood reported to prison the same day that former Chester County Supervisor Shane Stuart pleaded guilty to drug and misconduct charges in Chester County. Stuart and Underwood were both charged by South Carolina prosecutors with corruption charges.

Underwood was indicted by a South Carolina state grand jury and still faces South Carolina grand jury charges that are pending even with the federal conviction, state prosecutors said Friday.

What happens now?

Underwood ‘s federal sentence is for 46 to 54 months.

The appeal of his conviction and sentence continues in the U.S. Fourth Circuit Court of Appeals.

It remains unclear when that appeal will be heard.

This story was originally published October 14, 2022 at 4:48 PM.

Andrew Dys
The Herald
Andrew Dys covers breaking news and public safety for The Herald, where he has been a reporter and columnist since 2000. He has won 51 South Carolina Press Association awards for his coverage of crime, race, justice, and people. He is author of the book “Slice of Dys” and his work is in the U.S. Library of Congress.
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