South Carolina

In three-piece suits, he ‘politely’ robbed Carolina banks in the ’80s. Now he’s free

After 31 years, the question lingers. Why?

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Gentleman Bandit

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


It was a Friday, around noon, in a setting made for a travel brochure. Drew Mills Dobson, 36, eased through the gates of his Rose Hill Plantation home in a recently purchased red Mercedes-Benz convertible.

His life appeared to be picture-perfect.

He was well-known on Hilton Head Island as an agent with a leading real estate company, as a Sunday school teacher with two children and as the son of one of the island’s most respected couples, retired U.S. Army general and World War II hero John William “Jack” Dobson and his wife, “Magnolia.”

His wife had been the editor of a local magazine, a columnist in The Hilton Head News, the head of public relations for the phone company and a second-grade teacher at a private school. Together, they were featured raising champagne glasses on the beach in an advertisement for a Hilton Head resort.

But to the FBI agents who swarmed his car that day in June 1988, he was someone far different: an armed bank robber who had terrorized employees during a spree that lasted almost a year.

He was dubbed the “Gentleman Bandit” because he wore three-piece suits and was often described as polite as he pulled the heists. But there was nothing gentlemanly about his actions.

Twice, he even held bank employees hostage overnight in their own homes, wielding a loaded pistol and warning of a ninja warrior watching from the woods outside.

Before dusk that late spring day, as the agents drove with their man along the tree-draped blacktop that hugs the coastline to the Charleston County jail, the soft-spoken suspect said, “Let’s just get this over with.” He then described in detail how he had robbed five banks in South Carolina, North Carolina and Florida over a 10-month period, making off with $485,000.

Today, 31 years later, Dobson is free. He walked out of a federal prison in Butner, N.C., in February, at age 67, a quiet ending to one of the most staggering chapters in the rich lore of South Carolina’s Lowcountry.

Since that day, in a series of interviews with The Island Packet, Dobson has tried to explain how a quiet, unassuming husband and father turned into a man whose actions still anger his victims. He is sorry, he said. He is embarrassed, he said. He got what he deserved, he said.

But why did he do it?

That answer is much more complicated.

The FBI moves in

The FBI had their man, just three days after his last bank robbery, and one day after his wife alerted authorities to suspicious materials she found in his car.

Agents discovered $19,600 in cash lying on the front seat of his Mercedes-Benz and another $1,100 on Dobson. They seized a loaded 9mm semi-automatic pistol. Also at hand was a container of silver hair dye, four mustache boxes and a container for a fake beard.

That afternoon, agents opened a Bluffton self-service storage unit and found a sawed-off shotgun wrapped in a navy blue sweatshirt and an undetermined amount of money, still stacked in separate denominations. They found materials to make fake scars, bank diagrams drawn on notebook paper, surgical gloves and wigs.

That night in June 1988 would be Dobson’s first of more than 11,000 nights in jail.

Until Feb. 8.

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Drew Dobson hugged by his granddaughter, Finley, immediately after walking out of the Federal Correctional Institution in Butner, North Carolina, seen in the background. Submitted

He was picked up at the prison by his guardian angel.

He was hugged in the parking lot by his granddaughter.

“That was about a 5-minute hug,” Dobson said. “It was like, ‘Don’t move until I get all of this out.’”

And now, even after 31 years, the question lingers.

Why?

Why?

Dobson has had a lot of time to figure out why his life “went off the rails,” as he calls it.

“I was trying to come to grips with where all this came from and one of the psychiatrists that I had gone to at one time said, ‘Well, exactly what kind of gas got put in your tank, we’ll address over a period of time and try to figure out, but the accelerator was pushed to the floor and you were screaming along. Prison, being arrested, was the wall that you hit and could go no farther.’

“I always liked that analogy. It seems apt for what was going on in my life before. So, yes, thank God I was off the road, so to speak.”

He commends his ex-wife for getting him off the road. In court, he credited her with making courageous decisions.

Marguerite testified for the defense that Dobson had gone into a depression in the spring prior to his first bank robbery in August 1987. He stayed in bed for three weeks and the “old Drew” never returned, she said. She said he became cold and distant, and his trademark patience was replaced with an angry temper.

“Am I glad I was stopped? Yes,” Dobson said on the “Oprah Winfrey Show” in 1992.

By then, Marguerite was remarried. She said Dobson’s apologies did not seem sincere. She sat in a Chicago studio with Oprah while Dobson appeared via satellite from the federal prison in Talladega, Alabama.

“Instead of being the ‘Gentleman Bandit,’ I would have become an absolutely horrible monster,” Dobson told Oprah.

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This photo of a television screen shows an interview with Drew Mills Dobson and his former wife Marguerite Kelly on “The Oprah Winfrey Show” on Oct. 29, 1992 titled titled “People Who Have Been Married to a Dr. Jekyll and Mr. Hyde Personality.” Staff photo

‘Find some answers’

Bank employees testified in court that Dobson told them robbing banks was exhilarating.

Dobson testified that after robbing his first bank in Lexington, South Carolina, “I felt like I could do anything.”

Others argued that Dobson was bipolar or schizophrenic.

One court document said his family had a history of mental illness. Later, a jury was allowed to hear that his only sibling, an older sister, committed suicide. And lawyers argued whether the jury could be told of more than one alleged attempt by Dobson to harm himself in prison.

But an FBI agent testified that robbing banks had a more practical purpose for a man who seemed perfectly sane.

Dobson said during his confession that he was having financial difficulties about a year prior to his arrest.

“He said he was $10,000 in debt and had no income coming in, so he decided he would start robbing banks,” the agent testified.

Dobson said on the witness stand: “It was more important to me to run around and be seen with possessions that were invariably ostentatious.”

FBI agents said $213,000 in cash and cashier’s checks was recovered of more than $485,000 taken. Most of the recovered money was from the $144,000 heist in his last robbery in Jacksonville, Florida, three days before his arrest.

Most of the rest of it was spent.

Dobson said that he put away his credit cards and spent lavishly with cash. Around town, stories were told of Dobson tipping a babysitter $50.

He left his job with the Lighthouse real estate firm to become self-employed, telling some people he was in the import/export business or interior design.

He testified that he had to burn $60,000 cash because it was stained with red dye from a bank.

Dobson told the court he took trips to Asia, made a down payment on a home in Aiken, and bought his wife a horse. He told her the money was coming from commercial real estate closings.

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Aiken (S.C.) Standard

But today, Dobson says it was not really about money.

He refers to that period of his life as a brief episode.

And he said he has come to terms with whatever it was that derailed his life.

He said he had to wonder if he were capable of the terrorizing robberies, what else was he capable of doing.

“It didn’t make sense for a while afterward,” he said, “but I was eventually able to find some answers to it all and, frankly, that has helped because, to me, it wasn’t so much a matter of apportioning blame.

“I was able to come to terms with the ‘what’ and ‘why’ of the whole thing and that was enough,” he said.

And he stops there.

“I really don’t care to discuss any of that. That involves a number of private matters for myself and for my family.”

But he said, “Some of the answers I really didn’t like, but life is like that.

“Sometimes you’ve just got to look in the mirror and face yourself and say, ‘You need to work on this.’ It’s a process where you roll your sleeves up every morning and say, ‘OK, this is what our life is, as it is, and let’s make the most of it.’ ”

The robberies

Dobson’s first blush with bank robbery came while watching the “Unsolved Mysteries” TV show, which debuted early in the year he started robbing banks.

“So when this idea just took hold, I mean I can remember the day,” he said. “I was sitting in a movie theater in Columbia, South Carolina, up there on some business, just taking a break, and I just turned a corner somewhere along there and said, I’m going to rob a bank.”

He said he didn’t know how to do it, but he thought of that TV episode, where robbers were the first to arrive at a bank for the day, or even held employees hostage overnight before going to the bank early the next day.

“Other than that, there was some training I had acquired in the military and the rest was just moving ahead blindly,” Dobson said.

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Drew Dobson in 2019. Submitted

He does not want to talk about the particulars of robbing a bank.

He instead tells a story from prison that he said “puts the whole thing in the proper perspective.”

Dobson was eating in prison with a couple of friends, when a stranger broke prison etiquette and joined them. He knew of Dobson from his appearance on the Oprah show, and wanted to hear how he robbed banks.

“And I looked at him and said, ‘Let me understand this. You want me to tell you all the real inside scoop of how I robbed banks and everything, right?’

“He said, ‘Yeah, yeah.’

“I said, ‘Have I got this right? You want somebody who is in prison for robbing banks to tell you how they rob banks? What’s wrong with this story, fellow? I mean, look where we are. I was an idiot. And you are too. Go away.”

The method

Dobson’s trial showed that he meticulously planned the robberies, and went to great lengths not to get caught.

FBI agents testified that while most bank robberies last a minute, Dobson’s could last 12 hours or more.

The public record shows that Dobson generally would drive to a city, park at the airport, take a rental car to an office or apartment complex near the bank, then walk to the bank. He would generally be the first one there in the morning.

Before and after stuffing a brown valise with cash from the vault, he might bind employees to chairs with surgical tape, or force them into a closet. One morning, he was answering the bank phone while employees were restrained, ending up putting all lines on hold.

He would take a bank employee’s car back to his car or his rental car. He sometimes called the bank later to tell where he’d left the employee’s car.

In the banks, Dobson was alternately calm and nervous and agitated, sometimes visibly sweating as he forced employees to give access to the vault, according to trial testimony.

He once called back later to check on an employee who fell over while tied to a chair. And at one bank he apologized for stuffing six employees into a small closet that he nailed shut.

Dobson testified that the sawed-off shotgun was never loaded.

But at his last two robberies — in Charlotte and Jacksonville — Dobson went to the homes of bank managers the night before the robbery so they could go together to open the bank the next day.

In Charlotte, Dobson got into the house by saying he was a bank inspector and needed to talk to the assistant branch manager, who was lying sick in the bedroom upstairs. In Jacksonville, he posed as someone interested in a car listed for sale.

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Once in the homes, he would hold a 9mm pistol on the manager and spouse while sitting up all night, perhaps drinking beer, mixing lies about serving in Vietnam with details of how he’d robbed other banks, planning every detail of what was to come, and threatening harm if they did not do as they were told.

Victims testified that Dobson claimed he enjoyed throwing Viet Cong from helicopters while in the Vietnam War. He said he had contracted AIDS and had only a year to live so he had nothing to lose by robbing banks.

Neither claim was true.

The victims

Victims told the court they were terrified.

They said Dobson threatened to kill them, and their families, if they messed up. He spoke into a walkie-talkie, reading in the name and address from an employee’s identification card, or giving an update on his progress — but no one ever heard any response.

Dobson always worked alone.

“I don’t think anyone understands the horror of what it’s like to have a sawed-off shotgun in your back,” one bank manager testified. “He is a very calculating individual ... I feel sorry for his family.”

Bank employees said the robber appeared to be bearded, but his blue eyes gave him away in court.

“That’s him,” one said from the witness stand, pointing straight at Dobson. “He has the coldest eyes I’ve ever seen in my life.”

One victim stared at Dobson. He said he had promised Dobson that one day he would see him in court.

Dobson testified, “I knew it was illegal, but I wanted the money. The whole idea was to gain control of the people so they would do what I wanted, then leave.”

He also testified that he did not realize until the trial how much the bank employees were victimized. And more than once, he apologized.

In a sentencing hearing, he said, “Somehow, saying I did it and I’m sorry just doesn’t seem enough, and yet that’s all I have to say.”

The experience literally changed the life of the manager of the C&S Bank in Lexington, South Carolina — the first bank Dobson robbed.

After the robbery, she was introduced to a victim advocate through the U.S. Attorney’s office in Columbia. She decided she wanted to become one of these professionals who offers emotional support while helping victims of crime navigate the criminal justice system.

“It changed my life to serve others,” Margaret Frierson said in a recent telephone interview. She did not want to say anything else about Dobson or her experience.

For 22 years, she directed the South Carolina office of the National Center for Missing and Exploited Children. She was an advocate for the parents of missing children, and the children themselves, when found.

In a professional publication celebrating her career upon retirement, she said: “God puts you in the places you need to be.”

The trial

Dobson’s day in court lasted six days in the spring of 1989.

Charges in the three South Carolina robberies were merged into a single trial at the federal courthouse in Columbia. Dobson faced three counts of armed bank robbery and three counts of using a firearm during a crime of violence.

His guilt in taking a total of $177,358 from those three institutions was never in question.

But he pleaded not guilty by reason of insanity.

That defense was hinted at in Dobson’s initial arraignment, when federal public defender Park Small filed a motion seeking court approval of a psychiatric examination.

The motion said “something snapped in Dobson’s mind” about 18 months earlier. It said Dobson “has an absolutely clear criminal record and a history of being a normally functioning person in his business, his church and his family” until confessing to five bank robberies “that are somewhat of a bizarre nature.”

The motion was granted and Dobson underwent extensive psychiatric examination more than once. A judge had to rule that he was competent to stand trial.

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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

When his trial began on May 1, 1989, Dobson was represented before U.S. District Judge Karen Henderson by a former assistant U.S. attorney, Lionel S. Lofton of Charleston. The case was prosecuted by assistant U.S. Attorney John Barton. The jury was made up of nine women and three men.

The prosecution hammered away at testimony that Dobson was an intelligent, successful, thorough, cunning bank robber.

A bank manager testified that he seemed to know the layout of the bank, the employees’ schedules, habits and the colors of their cars.

This was not the work of an insane person, prosecutors said.

Barton told jurors in closing arguments that it would be an insult to all the mentally ill people in the country if they decided Dobson was insane.

The jury heard more than a day of testimony from dueling psychiatrists.

A psychiatrist for the defense testified that Dobson suffered from “a bipolar disorder” or manic-depression. It was also said he was schizophrenic.

But a psychiatrist with the federal prison system who had done extensive testing of Dobson testified that tests failed to show a mental disorder and indicated he was “probably malingering,” or feigning mental illness.

Dobson’s attorney leaned on testimony that Dobson had slashed his side and chest while at a prison psychiatric ward because he thought bugs were crawling on his skin.

Sensational headlines during the trial included: “Dobson testifies he heard God’s voice.” The voice, he said, told him that he was damned and his days were numbered.

Dobson testified, “I’d turn on a radio and hear my thoughts broadcast.”

By the time of the trial, Dobson was taking five different medications for anxiety and depression, and his wife said he was like a zombie on the stand.

Dobson says he was telling the truth in court.

“The diagnosis that the government came up with after they evaluated me was, in layman’s terms, due to some fairly catastrophic emotional and cognitive things that were going on in my life and the stress of it,” Dobson said. “I was paranoid because I was doing things I shouldn’t have been doing. Any hallucinations I was experiencing were temporary and more stress-related than it was a true, full-blown psychotic episode or schizophrenic episode.”

And he says he agreed with the prosecution.

“You know, by the time the trial was over, I frankly held no hope. I mean I’m sitting there thinking, the whole thing just boils down to the fact that, no, I wasn’t insane. The planning was too meticulous, specifically in the efforts not to be caught, not to be recognized. It wasn’t some sort of mad endeavor when I just break into banks, going somewhat berserk, and robbed them.”

The verdict

The jury deliberated for only one hour.

“So, I remember my lawyer, Lionel (Lofton), was standing there next to me,” Dobson said. “I knew something was up because we went to stand in front of the judge and in my peripheral vision I noticed a whole little squad of marshals sort of materialized around me and I thought, ‘Hmm, OK, this is going to be pretty much what I suspected,’ and sure enough …”

Dobson was found guilty on all six counts.

Lofton, his attorney, said afterward he would not do anything differently, even though it is hard to prove insanity.

“The tragedy in this case,” he said at the time, “is that I think Drew is really sick.”

Today, Dobson says that in hindsight he wishes he had stuck to his gut, which was not to plead insanity but to confess in court just as he had done with the FBI agents driving up U.S. 17 to Charleston on the day he was arrested.

“Frankly I agreed with the jury,” he said. “They came back and said, ‘No, we don’t think he was insane and we do think he robbed five banks,’ and handed me back to the judge.”

The judge threw the book at him.

Click here to read the next chapter of Gentleman Bandit.

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Senior editor David Lauderdale has been a Lowcountry journalist for more than 40 years. He oversees the editorial page, writes opinion, and tells the stories of our community. His columns have twice won McClatchy’s President’s Award. He grew up in Atlanta, but Hilton Head Island is home.

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