David Lauderdale

Bank exec held hostage overnight by the Gentleman Bandit recalls night of terror

This clipping ran on the front page of the March 3, 1988 Charlotte (N.C.) Observer in which a bank executive and his wife were held hostage by gun point the night before by Drew Mills Dobson.
It was a surreal night with ‘Robber Man’ and ‘Ninja Man.’

More from the series

Gentleman Bandit

He’s spent the past three decades behind bars for robbing banks in the Carolinas. Now, he’s free.

Herb Bennett was not feeling well on the night that changed his life forever.

He was upstairs in bed, where he’d fallen asleep early while reading The Charlotte Observer.

His wife, Lea Bennett, answered the doorbell around 8 p.m. at their home near Charlotte’s Myers Park Country Club on March 1, 1988.

There stood a gray-haired man in a three-piece suit, carrying a large leather brief case. He showed her a badge and said he was a bank examiner, and he needed to talk to Herb Bennett.

The Bennetts were a young couple then, in their 20s, married a couple of years, and he was the assistant manager at the First Union National Bank branch at the Park Road Shopping Center.

Lea Bennett went upstairs. She tapped her husband on the shoulder and told him about the man at the door.

“I said, ‘OK, I think I know what it’s about,’ “ Herb Bennett recalled in a recent telephone interview with The Island Packet and Beaufort Gazette. “I had no idea, but I could tell she was scared to death.”

When they opened the bedroom door, there stood the man, pointing a 9 mm pistol at them, his arms straight out.

“He had the hammer cocked, and he said, ‘Get down on the floor and don’t make a sound,’“ Herb Bennett said. “He had us down on the floor, looking up like turtles, with a fully-loaded 9 mm about 3 feet over our heads and he let us know he would use it.”

The first thing he did was confirm that the man on the floor was the Herb Bennett who worked at First Union.

“He stumbled over either the bank name or my name or something, and he had a great big bead of sweat rolling down his forehead,” Herb Bennett said. “He was as nervous as we were scared, and then right after that, while we were down on the floor, he said, ‘I’m here to rob your bank,’ and once he said that, there was a little bit of a sigh of relief that he wasn’t just going to kill us.”

The surreal night to follow would make for prime testimony against the intruder.

It was testimony about a man with faked gray hair and a big plastic scar in the corner of one eye who commandeered their home. He reviewed time and again a plan for robbing the First Union bank early in the morning. He said he’d dropped Viet Cong from a helicopter in Vietnam. He warned that a man dressed as a ninja warrior was watching from outside and enjoyed harming people who did not do as they were told.

About a year later, the Bennetts told about it in a witness chair at the federal courthouse in Columbia, South Carolina, where the man at the door, Drew Mills Dobson of Bluffton, was convicted of being a serial bank robber.

But it’s not the experience of that crazy night that troubles the Bennetts 31 years later. A personal loss from that same year — 1988 — still haunts them.

‘Gentleman bandit’

Lea Bennett’s friends have always called her a good listener. Her husband calls her a chatter box.

So the Bennetts and the person they refer to as “Robber Man” talked for hours that night in a kitchen nook so tiny “we could have held hands,” Herb Bennett said.

“He told us exactly how he robbed (three) banks in South Carolina,” he said. “He told us why. He needed money and he came up with the idea.

“The fellow gave us a lot of insights about himself. He talked a lot. He mixed a lot of fiction in, but he told a lot about himself.”

Drew Mills Dobson leaves U.S. District Court in Columbia on July 6, 1988 after his arraignment on three counts of robbery in South Carolina. The former Hilton Head Island real estate salesman pleaded not guilty before a U.S. Magistrate. The Associated Press

The intruder yanked out all the phone cords but one, and had Lea Bennett tape what he said was a bomb to that one. That was a threat — like the fictional person they referred to as “Ninja Man” — to not mess up what amounted to a three-way bargain:

Herb Bennett would go with Dobson to the bank in the morning and get money out of the safe, Lea Bennett would stay in the home and not alert anyone and Dobson would not hurt them or anyone at the bank.

“He didn’t mistreat us,” Herb Bennett said. “He didn’t knock us around. He didn’t harm us and he could have harmed us. Plus he had on a three-piece suit and Gucci shoes.

“We were treated more kindly and more gently than other victims, BUT I’ll kill you ...”

Sometime around 2 or 3 a.m., the Bennetts were taken back to the bedroom and bound with packing tape.

Around 6:45 a.m., Dobson and Herb Bennett left for the bank in Bennett’s green 1980 BMW.

Lea Bennett testified that her two hands were bound to bedposts, and as he was binding her, Dobson said to himself, “Oh Drew, I can’t believe you have to do this.”

Herb Bennett said he knew half the combination to the bank vault, and when the branch manager arrived, she knew the other half. At gunpoint, they took out the money, which was was stuffed into the large brief case. Dobson left in Bennett’s car with what officials would later say was $163,985. He drove to his car, which he had parked at an apartment complex across from the country club.

Lea Bennett freed herself, but never left the house. Her husband rode home with the FBI or Charlotte police. A bomb squad came to take care of the supposed bomb in the telephone.

The baby

Herb Bennett chokes up retelling the story.

He says that in Charlotte, with its rich banking history, he was always linked to that larger-than-life story.

He usually gives only abbreviated versions of it, and his wife doesn’t like to talk about it at all. Few people ask about it since they moved out of state 20 years ago. They asked that their new hometown not be included in this story.

Herb Bennett chokes up for a different reason.

“My wife was expecting our first child when that (the crime) happened,” he said. “We were ecstatic and we hadn’t told anybody. That was March 1 and the baby was due in November. And we got a call from the doctor in August saying there was a problem, and then they told us, well, we think it’s OK, and then it turned out they were right in the first place.”

Baby Kate was born with a heart defect.

“She was a beautiful baby — an 8-pound baby with a bad heart. It wasn’t congenital. And at the time, they weren’t able to do surgery to correct it. Today, they would have done either surgery to correct it, or a heart transplant.”

Kate lived 10 days, but never came home.

To the Bennetts, the robbery and Kate’s passing are inseparable events.

“It’s not fair, but that’s the imprint that remains,” Herb Bennett said. “It’s just bad luck, I guess, but … It was just a bad year because of that. It was a rough year.”

Today, the Bennetts have a child in college, one who graduated a year ago — and a daughter who was born one year after Kate died.

“So there are still blessings,” Herb Bennett said. “Maybe if our first child hadn’t died, we wouldn’t have our second child, so you can look at it that way too.”

Ironically, Charlotte Observer reporting of the bank robbery includes this:

“(Dobson) also told them he knew they had no children, because he called two weeks ago posing as a Charlotte Observer employee doing a survey. If they had children, he wouldn’t have bothered them, the man said.”

Dobson says today, “So does that make me some kind of moral bandit? No. It just means that I was pretty screwed up. I had it right and I had it horribly wrong, all at the same time.”


Not long after the Bennetts moved away, that house on Sharon Road burned to the ground.

And over time, Herb Bennett said he has slowly found a way to forgive the intruder he will refer to only as “Robber Man.”

He said he cannot speak for his wife in that regard, and that she is still upset about it.

“I actually felt sorry for him,” Herb Bennett said. “I just feel sorry for anyone who throws his life away. Thirty-one years in prison is unimaginable. And to be separated from your family, your parents and your children. It’s just a horrible, horrible thing and, over time, I think you have to forgive.”

This clipping from the March 3, 1988 Charlotte (N.C.) Observer details when Drew Mills Dobson held a bank executive and his wife hostage by gun point the night before robbing the bank in the morning. The Charlotte (N.C.) Observer

He does not think Dobson should have served more of his 78-year sentence for robbing five banks in three states over a 10-month period.

“No, I don’t feel that way at all,” he said. “The damage has been done, to his family and to my family. And to society, I guess. And he paid a dear price.”

Herb Bennett said that at the trial, Dobson’s father, a retired U.S. Army general, “came and said hello to me and apologized, saying he couldn’t believe what his son had done. I felt sorry for him.”

Long before his trial, Dobson mailed an apology to the Bennetts — something he said his lawyers told him to quit doing.

“He wrote us a letter from prison,” Herb Bennett said. “It was a 1-page or 2-page handwritten letter written in pencil.”

Herb Bennett said he didn’t pay much attention to it. He didn’t know whether to believe it.

Dobson, who had previously been convicted of robbing three banks in South Carolina, pleaded guilty without a trial to bank robbery and hostage-taking in the Charlotte case. He was sentenced to 10 years to run concurrently with his existing 78-year sentence. He earlier was sentenced to 10 years for robbing a Jacksonville, Florida, savings and loan, also to run concurrently.

Prosecutors said they accepted the plea in part so hostage victims would not have to testify again. Herb Bennett said he appreciated that.

At the North Carolina sentencing hearing, which the Bennetts did not attend, Dobson told the judge, “Not only am I sorry, but I realize what I have done.”

He said he had come to realize he had harmed more people other than himself and his family.

“I realized what I have done to these people. There is a flaw in my character ... a weakness in my sense of morality that just took to full flowering.”

Read the next chapter of Gentleman Bandit here.