For the third time since July, the woman he blames for killing his brother has missed her court date, and Gentry is feeling frustrated.
Surrounded by TV cameras and reporters, Gentry stands on the steps of the Stanly County courthouse and rails against the town and its courts, which he feels keep giving 78-year-old Betty Neumar a pass.
He singles out the district attorney, Michael Parker, and questions whether Parker, who lost the Democratic primary for his office in May, even wants to try the case before he is replaced. At the same time, he lauds Sheriff Rick Burris for reopening the file on Neumar more than two years ago.
"It's one of the most aggravating things I've ever done in my life -- in fact, it's been a third of my life," Gentry said.
He keeps on talking, giving the TV crews their choice of colorful and incendiary quotes for their evening broadcasts. He handles interviews like someone who has done hundreds, a milestone he has likely reached in the nearly 25 years he has lobbied for help to find and punish his brother's killer.
"I'm just sitting here, holding it again, like always," Gentry said.
Then, as if he has just realized what his statement means, a look of defeat crosses Gentry's face momentarily before it is replaced with one of anger.
"I don't know what to do anymore," he said. "My brother died for nothing."
At 65 years old, Gentry is friendly, loud and outspoken -- the kind of person who doesn't mind speaking out in a quiet courtroom.
He has lived most of his life in and around Albemarle, and it shows. He drawls a greeting to the deputy staffing the court's metal detector and tells a visitor a tale from the man's early days with the sheriff's department.
Sitting in the packed courtroom, Gentry motions to a white-bearded man several seats away and inquires about his daughter. When they finish talking, Gentry adds, matter-of-factly, that the man is a "darn good" banjo picker.
He is like this with everyone, from the sheriff ("a fine man who should be re-lected"), to the investigator who helped on Neumar's case and recently lost 56 pounds ("His underwear don't even fit!").
Gentry is one of eight siblings and the youngest of the four brothers who grew up in the cotton fields of Norwood, just outside Albemarle. Their father worked as a sharecropper for several years, and Gentry said they never had much money.
During a drive through his hometown, he gestures out the car's windows to the places that made up his early life.
There is a small lake with a wooded island in the middle where Gentry used to fish with his brothers; a store where he worked his first job; and the cotton fields he and his siblings had to pick so often that, Gentry says, he wouldn't wear cotton for years.
Then there are places he identifies with less enthusiasm. The one-story brick house where his brother lived with Neumar and was killed; the post he leaned against as Neumar pulled into the driveway and gave him her alibi: that she'd been in Augusta when the shooting occurred; the hillside spot where Harold was buried.
Gentry describes his deceased brother as "likable as you'd want to know until he got drinking."
He said Harold met Neumar in Florida in the late 1960s.
"He told me before he had met somebody he liked pretty good and the next thing you knew, he brought her up and got married," Gentry said.
When his brother retired from the Army in the mid-1970s, Gentry said, Harold moved back to Norwood and built a house on a piece of land given to him by his sister -- the house where he would die.
Gentry said Neumar turned the home into an "icebox." She kept Harold busy with a steady stream of chores, written on a long roll of paper.
When family visited, Gentry said, Neumar would ignore them. Before long, he just stopped.
A promise kept
Two decades later, Gentry can seem a bit impatient when he talks about the case, but it might be because he is running low on time.
A diabetic, Gentry also suffers from vertigo and heart problems. He can't buckle himself into a car seat belt because it could interfere with his defibrillator. Recently, he was in the hospital for pneumonia and kidney failure.
Still, he does his best not to miss a single court hearing, and he often acts as a de facto spokesman for the case, gathering details from the authorities and passing them along to reporters to keep the story alive.
He does this to fulfill a promise he made years ago.
Authorities found Harold Gentry's bullet-ridden body July 14, 1986, about a day after he was shot dead, authorities allege, by a hit man hired by Neumar. Gentry said his brother's body was swollen and "looked 300 pounds" by the time he finally saw him.
At that time, Gentry said, he swore to track down the killer.
"I told him I would find who done it if it's the last thing I ever done," he said.
A long, hard battle
Through persistence and regular visits to the sheriff's office, Gentry finally got the case reopened and in 2008, Neumar was arrested outside her Cambridge Court home in Augusta.
She is facing three counts of solicitation to commit first-degree murder, yet her case has lingered in the courts for more than two years.
For their part, Ginger Efrid, a spokeswoman for the Stanly County District Attorney's Office, said officials have been doing all they could to move the case along, which is why the date for Neumar's arraignment and trial were set this summer.
"In no way, shape or form is the state dragging its feet on this case," Efrid said. "We have moved forward very diligently. We have tried to do these things and things outside our control have come up."
Neumar, who is out on bond and living in Louisiana, was scheduled to be arraigned Monday on two of the charges, but failed to appear because of a recent hysterectomy. Neumar missed two hearings in early August for health reasons before making the trip to Albemarle to attend a hearing on whether to retain her attorney, Charles Parnell, later that month.
At Monday's hearing, officials said she would not be able to travel for months, making it unclear whether the trial could begin as scheduled in December.
Although he is angry and tired of delay, Gentry said he will see the case through to the end.
It is a balmy 80 degrees in the midday sun when Gentry stands on the hillside Albemarle cemetery where his brother is laid to rest. The memorial overlooks a busy road, and Gentry says he drives past the spot regularly but doesn't always stop because he "can't stand it."
As he talks about his brother, his eyes well up for the briefest of moments before returning to normal.
"I come down here I get so mad sometimes that I'm shaking the whole way home," he said.