David Lauderdale

How did the Gentleman Bandit survive 3 decades behind bars? Crocheting helped.

Federal Correctional Institute in Talladega, Alabama
Stranger in a strange land: Clock ticks slowly in a 78-year prison sentence.

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.


Drew Mills Dobson was 37 years old when he was slapped with 78 years behind bars.

He would be free when he was 115.

The federal judge had no pity on the Hilton Head Island businessman from a respected family who suddenly turned into the “Gentleman Bandit” in 1987.

Dobson ended up serving 30 years and eight months, walking free on Feb. 8 at age 67.

In prison, the former Sunday school teacher said, “You meet some good people who got caught up in some bad things. You meet some bad people who got caught up in exactly what they seemed to be on earth to do. And then you meet some nightmares that you hope are never around your own family, or anyone else’s for that matter.”

Dobson was locked up for robbing five banks in three states over a 10-month period, bagging $485,000. He carried a sawed-off shotgun, but was called the “Gentleman Bandit” because he wore three-piece suits and sometimes treated bank employees politely.

That puzzling spree ended in June 1988 when the FBI arrested Dobson near his Rose Hill Plantation home in Bluffton, acting on a tip from his wife at the time.

The jury didn’t buy his plea of not guilty by reason of insanity. And the judge hit him with the maximum sentence on each of the six counts he faced.

His appeal fell flat.

And then as his life behind bars began, one of the most sensational stories to rock the South Carolina Lowcountry was all but forgotten.

In a series of telephone interviews since his release, Dobson talked about how he survived behind bars — and how he dealt with who he is, and where he was.

“The trick to doing the time,” he said, “is just to stay involved and stay extremely busy in as many things as you are interested in.”

He wrote a series of fantasy novels, he took self-help classes, he played guitar, he taught guitar, he worked out, he mastered crochet, and he worked at a job making things like Kevlar vests and furniture for the military.

“Just staying so busy that when you put your head on the pillow at night,” he said, “you were too tired to think about doing anything that you couldn’t be doing.”

The Atlanta Pen

“Can you imagine, and this is probably politically incorrect, a 37-year-old WASP who looks about as criminal as a book, landing someplace like the penitentiary in Atlanta, where the real nightmares are?,” Dobson asked.

“So you land there, and yeah, it was stressful. It was interesting in a you-better-keep-yourself-alive way.”

He would serve time in federal prisons in Talladega, Alabama; Atlanta; Edgefield, South Carolina; Jesup, Georgia; the Coleman prison complex in Florida; and Butner, North Carolina.

“Without going into it in any real detail, I had a few interesting cellmates,” Dobson said.

“One of the things you learn very quickly is that the most, for me at least, stressful point in prison was in the cell.

“When you get locked in there at night and can’t get out until the next morning, when that is your quietest time, a good celly is a godsend, and a bad celly means you better come up with a move — either you’re leaving or they’re leaving, but it’s not worth the drama.”

Good behavior meant transfers to lower-security prisons. He said prison works on a point system. You get old, you stay out of trouble, your points come down. If you don’t stay out of trouble, they go back up.

“I met somebody who came in with 15 years, and after three or four murders within the prison, he turned it into a solid lifetime sentence.

“You still have choices.”

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‘Little voices’

Dobson had no rehearsal for life in prison.

He was an Army brat, born in Munich, Germany, when his father was serving in Austria, a colonel in the U.S. Army on the march to becoming brigadier general.

Drew Dobson was educated at the Culver Military Academy in Indiana, which his father attended and later served as superintendent before retiring to Hilton Head in 1970.

That’s about the time Drew Dobson began a short stint at the University of South Carolina in Columbia, “where I decided that I was going to play rock and blues, grow my hair long and grow a beard.”

He began to stick out his thumb “and go wherever you go and come back in a month or two.”

He fell in love, was married and lived in Nashville, doing some studio work and a little recording, earning a black belt in Tae Kwon Do and, as he says, starving.

Dobson decided to join the Army in 1975. He served in Korea. His wife and their little baby girl enjoyed it there, he said, but the marriage ended in divorce and Dobson won custody of baby Rachael.

The two of them landed on Hilton Head, where his parents, retired Gen. John W. “Jack” Dobson and “Magnolia,” were well-known in what was then a small community.

Dobson said that one morning his mother told him there was a job opening at Sea Pines Academy for a second-grade teacher’s assistant. She told him he’d look good and he’d probably have a good time. Dobson had such a good time he married that second-grade teacher.

Dobson would later write on his website: “That’s where I discovered what, of any possible career, was and could have been my most rewarding life’s work — teaching second grade.

“Looking back, I only wish I had followed the little voices inside of me and taken that fork in the road. Sadly, such is life and the follies of our choices.”

The old general

Dobson was in his fist prison, in Talladega, when he got a visit from his father.

Jack Dobson, with neat white hair and a chiseled face like John Wayne, dropped in after attending the dedication of the Ranger Memorial Monument at Fort Benning, Georgia.

“My father was a military officer and he’s got one of these commanding voices,” Dobson said, “and we’re sitting in the visiting room and he says, ‘You know, there’s a lot of wire and stuff around here.’

“I said, ‘Yeah, Dad, they’re pretty determined to keep us in here.’

“He said, ‘Well, it’s not like when I ESCAPED from the POW camp.’ ”

The word “escaped” seem to ring out three or four times. Guards jerked to attention. Dobson said he was cringing.

He answered questions as the guards went through their routine pat-down after a visit.

Yes, Jack Dobson was with the 1st Ranger Battalion in World War II when he was wounded and captured in Italy in 1944. His family was told he was killed in action. He ended up in a prison camp in eastern Germany, but escaped and walked halfway across Poland.

The senior Dobson left the service as deputy chief of operations of the Joint Chiefs of Staff, with the Distinguished Service Medal, the Silver Star, the Legion of Merit, the Bronze Star and the Purple Heart.

The old general never abandoned his son.

“Mom and Dad, my aunts and uncles, and consequently my daughter, maintained a good relationship with me through the whole thing,” Dobson said.

He said other people kept up with him as well.

And he said that in all those years, he met only one other prisoner from Hilton Head Island.

Drew Mills Dobson started robbing banks in the late 1980s and stole near half a million dollars in less than a year before getting caught.

‘Years of Bone and Ash’

Dobson became a master at crochet.

He made animals for his grandchildren, like Alice the Alligator, a 7-foot-long crocheted gator.

But music and books kept him the busiest in jail.

Reciting a typical day, he said:

“I’m normally up between 4 and 4:30 a.m., by 5 o’clock I’m writing.

“Once the day sort of woke up and got started, I would work out, or depending on what job I had at the time, I would go to that.

“And more working out. More writing. Music. Music. Music.”

He taught music classes in the evening, and on some nights played with a band — rock, sometimes jazz.

He also took a number of classes.

“Way back when, I got myself into everything from anger management to critical-thinking classes, to specific things that were related to myself going off the tracks for nine months and landing myself here,” he said.

The largest project to come out of it was a book — or a series of books — that he wrote with pen and paper, then had someone on the outside key into a computer.

The genre is fantasy, science fiction and historical fiction, according to a website he set up for the books while in prison.

Writing was really the first chapter in his life of incarceration.

It started when he was on the well-used mattresses of county jails during court appearances.

“Those jails are crowded,” Dobson said. “And you’re just sitting there with absolutely nothing to do.

“I would just sort of begin having these little mental exercises: what if I went back, to let’s say Britain in the 5th century, what book, what tool and what single medicine, if I was allowed to take one of those things, what would I do?”

Playing “what-if?” and writing it down got him through day after day of what he said was sort of like being a Connecticut Yankee in a county jail.

It led to a series of books set in the 5th century. He calls it “The Years of Bone and Ash.”

‘What’s the choice?’

The clock ticks slowly on a 78-year sentence.

He was convicted on six counts, so each count had its own prison term. His task was to work them off, one after the other.

He had just started his last segment when he was released. He was anticipating serving seven of those 10 years. But he said the parole board opted to release him earlier than he expected.

“I’ve taken this all in many small bites,” Dobson said.

“I don’t necessarily think in terms of one grand theme of it or anything. For any number of reasons, I made not just one but a series of very, very bad decisions. And that led to this.”

He said you cannot think about whether you’ve done your duty to society — whether you’ve served enough time, or too much time, for the harm inflicted on others.

“The sentence was pretty darned intimidating, but I didn’t do a lot of dwelling on it,” he said.

“People who knew me said, ‘Oh, this is unfair. People commit murder and do less time than that.’

“That is something I never tried to get into because that’s a worm that will really eat you alive.

“People have asked me over the years, ‘How do you do it?’ I say, ‘What’s the choice?’

“If I handle this as best as I can and successfully, then I’ll do my time and hopefully get out at some point. If I don’t handle this well, I’m still going to do my time but I’m going to do it in a way, or be somewhere, which is really much worse.

“So you just do the best you can do and spend a lot of time — and get fairly good at — picking yourself up and keeping going.”

‘Make Your Bed’

Dobson said there’s actually value in a long sentence.

“It’s one thing to say, ‘OK, I’m ready to get out now,’ ” Dobson said. “It’s another thing to stay in and to see how you handle the frustration and the disappointment and the anger and all of those things that follow because you’re not getting out.

“If you handle them, that’s OK. But if not, you’re going to encounter those same emotions and those same kinds of problems on the outside, and if you can’t deal with it now, you’re definitely not going to deal with it effectively out there.”

Dobson latched onto a commencement address that went viral in the spring of 2014. He even sent a copy of that speech — from retired Navy admiral William H. McRaven to seniors at the University of Texas — to his granddaughter at her high school graduation.

The theme of the former Navy SEAL’s speech, which was later made into a best-selling book called “Make Your Bed,” was: “If you can’t do the little things right, you’ll never do the big things right.”

Dobson said, “Literally, he gives the most honest, simple, and what I always considered honestly profound rationales for doing the most simple things, like starting your day by getting up and making up your bed.

“But those are the choices you have. You don’t have a choice about getting up. The rules are quite clear about that.

“And so, OK, here I am. I’m out right now. I don’t have the same regimentation. But I still get up every morning and I still make the bed, for the same reason I made it for 31 years in the prisons.

“Not because I have to. Because it represents something. It represents that I’m starting my day off accomplishing something.”

Now he makes up his bed in a different place, thanks to a guardian angel.

Click here to read chapter 3 of Gentleman Bandit.

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