David Lauderdale

‘Gentleman Bandit’ politely robbed SC and NC banks. Now after 30 years, he’s free

And now, even 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.

The “Gentleman Bandit” is free.

After almost 31 years in prison, Drew Mills Dobson walked out of a federal prison in Butner, North Carolina, on Feb. 8, a quiet ending to one of the most staggering chapters in the rich lore of South Carolina’s Lowcountry.

His story struck like lightning in the late 1980s, when Dobson was arrested near his Rose Hill Plantation home in Bluffton.

He was known on Hilton Head Island as an agent with a leading real estate company, a Sunday school teacher at First Presbyterian Church and 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.”

He had no criminal record. He had two children. His wife had been editor of a local magazine, head of publicity for the phone company and a second-grade teacher at a private school.

But that all came crashing down on June 17, 1988.

It was a Friday, around noon, in a setting made for a travel brochure. The 36-year-old businessman eased through the Rose Hill gates in a red 1975 Mercedes-Benz convertible that he had recently bought.

Suddenly, he was swarmed by FBI agents.

They were looking for a man the press dubbed the “Gentleman Bandit” because he wore three-piece suits and was often polite in a string of bank robberies.

They had their man.

Agents found $19,600 cash lying on the front seat, 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.

And before dusk, while driving the tree-draped blacktop that hugs the coastline up to the Charleston County jail, the agents heard the soft-spoken suspect say, “Let’s just get this over with.” He then described in detail how he had robbed five banks in three states over a 10-month period, making off with $485,000.

While he was called the Gentleman Bandit, the robberies were terrorizing events that still have bank-employee victims angry. Twice, he held bank employees hostage overnight in their own homes. Their lives flashed before their eyes as he wielded a loaded pistol and warned of a ninja warrior watching from the woods outside.

But that night in June 1988 — just three days after his last robbery, and the day after his wife alerted authorities to suspicious materials she found in his car — would be Dobson’s first of more than 11,000 nights in jail.

Until Feb. 8.

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.


Hug at prison.jpg
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

National notice

The “Gentleman Bandit” story went national in newspapers, and an Oprah Winfrey show titled, “People Who Have Been Married to a Dr. Jekyll and Mr. Hyde Personality.”

It also was told on an “FBI: The Untold Stories” episode called “Dapper Drew.”

Closer to home, the buzz was about specific robberies:

• The Citizens and Southern National Bank on Main Street in Lexington, near Columbia.

• A Rock Hill National Bank branch in York County.

• The Heritage Savings and Loan in Simpsonville, near Greenville.

• First Union National Bank in Charlotte.

• And First Federal Savings and Loan Association in Jacksonville, Florida.

In a series of telephone interviews with The Island Packet and Beaufort Gazette since his release, Dobson talked about the baby steps of freedom: getting a learner’s permit while also checking on Medicare, and what it’s like to fumble with a cell phone.

“Technologically, I’m a dinosaur,” he said. “I don’t even know if I’m a dinosaur. I might just be plankton.”

But he also talked about what happened, and why.

And how to survive in prison.

He said he is sorry.

“People said, ‘Well you didn’t shoot anybody, you didn’t kill anybody,’ Dobson said.

“My gosh, yeah, but just take a look at the record of what I did do, and look at the reality of how I did it, and then ask yourself the question I have over the years, which is basically, ‘OK, what if that happened to me or my family?’”

He said: “To start off with, by any stretch of the imagination, I got exactly what I deserved.”

And he talked about the “Gentleman Bandit” name that he dislikes, but will never escape.

“It’s just one more embarrassment in a long line of embarrassments,” he said.

Dobson_Oprah (1).jpg
In this photo taken of a television screen shows an interview with Drew Mills Dobson and his former wife Marguerite Kelly on the Oprah show on Oct. 29, 1992. Staff photo

Prison time wasn’t Dobson’s only punishment.

He must now begin restitution of some $150,000.

His ex-wife, then Marguerite Dobson, stood by him in court but divorced him not long after his long sentence began. Their son, who was 3, was adopted by her new husband and has been estranged from Dobson since that time. Efforts to reach Marguerite were unsuccessful.

Dobson missed the burials of both of his parents in the cemetery at their beloved West Point.

And he missed the high school ballgames on Hilton Head of his daughter by a previous marriage, Rachael Dobson Swick.

Rachael was only 11 when her father went to prison.

She was there with her husband and three children when Dobson walked out of prison, four days after his 67th birthday.

Following that long hug, Dobson climbed into an RV with a few boxes of manuscripts of books he’s been writing. And they took him home.


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 thanks his ex-wife with 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 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.

‘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 it from the $144,000 heist in his last robbery in Jacksonville, Florida, three days before his arrest.

Dobson said in an interview 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 the 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, telling her the money came from commercial real estate closings.

An Associated Press news article from the May 5, 1989 Aiken (S.C.) Standard newspaper where Drew Mills Dobson plead innocent by reason of insanity and told the courtroom God told him that he would be “damned to eternal hell.” 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 that debuted in January 1987.

“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 old 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.

Drew outside.jpg
Drew Dobson 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 did 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 lasted 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 tap 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 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 or agitated, sometimes 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 Jacksonsville — 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 one case, Dobson got into the house by saying he was a bank inspector and needed to talk to the manager, who was lying sick in the bedroom upstairs. Another time, 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.

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 was bearded, but his blue eyes still 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 on of these professionals who offer emotional support while helping victims 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.

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 $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.

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.

In more than a day of testimony by psychiatrists, a psychiatrist with the federal prison system who had done extensive testing of Dobson testified that 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.”

Psychiatrists for the defense testified that Dobson suffered from “a bipolar disorder”. It was also said he was schizophrenic.

By the time of the trial, he was taking five different medications for anxiety and depression.

The verdict

Today, Dobson says, “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 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 chapter 2 of Gentleman Bandit.

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