North Carolina

She only saw her dad on prison visits. Now the Gentleman Bandit lives in her basement

Drew Dobson and his daughter, Rachael, following his release from prison.
She was only 11 when this whole saga started. Now she has children that age.

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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.


Rachael Dobson Swick checked in at the prison to see her father on Feb. 8, just as she’d done for most of her life.

But this time, she didn’t come to visit for a few hours in assigned seats. She had come to take her father home.

Drew Mills Dobson had been in jail since she was 11. She was now 42.

Hilton Head Island was aghast 31 years ago that a businessman from a respected family turned out to be the “Gentleman Bandit” they’d been reading about in the news who robbed a string of banks in South Carolina, North Carolina and Florida.

Her dad was indeed the man who dressed nicely while robbing five banks in a 10-month period that led, at long last, to this moment at the federal prison in Butner, North Carolina.

When Rachael got there, a typically cold prison employee told her the process of release would take a while.

So she took the long walk back down the slope to the visitors’ parking lot. Her husband and three children were waiting there.

Drew Dobson 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

Five minutes later, a lean figure came walking their way.

“My husband says, ‘No that’s not him,’ ” Swick said. “He got closer and closer and I said, ‘Yes, that is him. That’s my father.’ And I started jogging up to him, and halfway there I think, ‘No, it’s not him’ because I got confused. We kept going and yeah, it truly was him.

“There were no prison clothes, and there were no guards yelling at him or chasing after him. It was like, OK, this is kind of strange, right? It was like, ‘Oh boy.’ ”

She thought her father would be serving at least seven more years of what started out to be a 78-year sentence, back when she was a kid and he was in his mid-30s. But a parole board decided about six months earlier to release him on Feb. 8.

Dobson’s first taste of freedom was a long hug from his oldest grandchild, now 21.

They walked back up to the prison to pick up Dobson’s earthly goods: a few cardboard boxes filled with manuscripts and research materials for fantasy novels he wrote in his prison cell.

Then they loaded into a roomy RV and left the prison in an oversized rearview mirror.

Life outside prison

An odd thing blindsided Dobson in his first hours of freedom.

“Something I had never thought of over all these years — pets,” he said.

His daughter’s household includes two dogs and two cats.

“My gosh, just sitting down and having one of them come stick its nose in my hands, or you start scratching and rubbing and you get a purr or you get licked, one or the other. It took me a couple of days to realize what a vacuum not having pets had been.”

He had to get a learner’s permit.

“My daughter took one of those things, I think they’re called selfies, of me driving, but in the foreground she looks thoroughly panicked.”

He had to learn how to use a credit card.

“Normally, everything stops while I try to figure out where to put the card and what button to push.”

He quickly realized that it takes help to be free.

“Now I understand much more clearly why there are so many guys going back to prison.

“The roadblocks that you run into just at your most vulnerable moment would be extremely difficult,” Dobson said in a series of telephone interviews since his release with The Island Packet and Beaufort Gazette.

It took days to set up a bank account, check in with Medicare and Social Security and the Veterans Administration.

“I had to prove citizenship. Everything led to three to five days, and it went on and on, and I kept thinking, what if I really needed that?”

Family changes

Swick’s two younger children, ages 10 and 11, are about the age she was when the whole saga started.

Her life was not the only one uprooted by the “Gentleman Bandit.”

Dobson’s wife at the time of the robberies divorced him, and their 3-year-old son was adopted with Dobson’s consent by his stepfather. They are estranged, he said.

“I harmed (my wife) and my son and everybody,” Dobson said. “They got through it however they got through it.”

The divorce did not surprise him. He said they had talked about it.

“I think I had pretty much ruined the whole thing with my conduct and everything,” he said.

When they met, she was a second-grade teacher and he got a job as her classroom assistant. At the time, Dobson was fighting in court for custody of Rachael, who was born in a previous marriage. He won custody.

Some time after Dobson went to prison and his wife divorced him, Rachael went to live with family friends on Hilton Head Island. She said she lived with two separate families until she went away to boarding school in Columbia for her senior year in high school.

Swick said that her late grandfather who had retired to Hilton Head, U.S. Army general and World War II hero John W. “Jack” Dobson, had power of attorney for her and her father.

Dobson said his parents were not able to raise Rachael, and that the families that took her in are “some very, very good people. She credits most of her mothering skills to them.

“She was able to grow up with the stability and the absolute assurance that people loved and cared for her, and that’s foundational for anybody growing up.”

Asked why she stuck by her father, Rachael said, “I kind of never thought about any other option.”

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.

Nothing to forgive

Hilton Head kids were never mean to Rachael.

“They knew my dad,” she said. “My dad was the fun dad. My dad was the cool dad. They had great memories of my dad. It wasn’t like, ‘Oh yeah, that was the creep that …’ you know. Nobody ever had that opinion of him.

“So I think everybody was just very empathetic for my situation, and I never had to make apologies. I was like, ‘I didn’t do this. Why would I feel badly?’ They may have said things behind my back, but I never found out about it.”

She’s more concerned now about her own children, and for that reason doesn’t want to reveal where she lives.

Rachael said she never struggled with forgiveness.

“I think this is one of those cases where the event does not define the person,” she said.

“It has controlled the majority of his life, but it certainly isn’t what has defined him.

“Prior to robbing banks, and after robbing banks, he was a good person with strong character. The character anomaly in his life is just so random and out of place.”

Despite that faith, it hasn’t been easy.

“I never blamed him,” she said. “I’m sure at some point in my early adulthood I did, but not to the degree that I actually in my heart was angry. I think it was more just like sadness.”

She said she did well in high school sports, even if it was in a “small arena.”

“Those are the things that I wish he’d been around for, because he would have been proud of me.

“He got to be proud of me from a distance, but not right there. That was the stuff that I got upset about. You missed this, you missed that.

“People would say, ‘You know, it was really selfish to do what he did because he didn’t think of the consequences that would happen to you.’

“ ‘OK. Yep. You’re right.’ But I can’t speak to that because, I don’t know, it never sat with me in that way.”

Only known as prisoner

Until Feb. 8, Dobson’s grandchildren knew him only as a prisoner.

“As soon as they could make the trip, Rachael brought them down for me to see,” Dobson said, “and with each and every one of them, we had to figure out how to at some point explain that this strange place where they always come and see Papa, that it is a prison.”

Virtually all visits were face-to-face in guarded rooms, not between thick glass.

“There were lots of people who would take me to visit him,” Rachael said. “My grandfather, mostly, but other people would take me on road trips to go and visit him.”

Drew Dobson with Rachel in snow.jpg
Drew Dobson and his daughter, Rachael Swick, following his release from prison on Feb. 8, 2019. Submitted

Over the years, communication evolved from handwritten letters, to phone calls that were very expensive, to eventually emails “that were a great filler between phone calls,” Swick said.

When Dobson’s parents died, and first one and then the other was buried at his father’s beloved West Point, Swick “took a wonderful series of pictures and made it into a little collage photo album and sent it to me, so I was there that way.”

Dobson said his daughter pushed him to quit talking about writing a book, and do it. He got one book in shape to be sold online, using money he’d earned working in the prisons, where he cleared about $200 per month.

“I always knew that he would be home at some point, but it always seemed so far off in the future,” she said. “Once we got to around the 10-year mark, it was the first I ever remember being flooded with any emotions. Excitement. And walking around the house just imagining, we’ll be sitting here in this room doing this.”

But when the day came for her family to make their last trip to the prison, there were no butterflies. She was more interested in getting the bed just right.

Mission in life

Dobson now has a room in the basement of his daughter’s home.

He has chores. He does the laundry. He offers extra supervision when the kids get off the school bus in the afternoon. He has done yard work.

He said he’s in demand as a guitarist with bands performing at what he finds to be a surprising number of breweries and wineries.

He’s working with an editor on his books.

He has a Facebook page.

He said he’s had two panic attacks since being released, both in busy, crowded places: a big-box store and a Washington Nationals game.

Dobson and his daughter have taken a weekend trip to Hilton Head Island, visiting the scenes of a life that seems so long ago. They went to the site of his parent’s home on Brams Point in Spanish Wells Plantation. They spent an afternoon with one of the families that took Rachael in as a child. They even rode through the gates at Rose Hill, where Dobson’s arrest in 1988 changed everything.

They’re beginning to eye a time that Dobson gets out on his own.

Swick works from home, doing corporate training in the mortgage lending business. Her husband recently got a nice promotion, and when they bought their new home, they chose it with Dobson in mind.

“My husband and I did a lot of talking about different situations or scenarios that might come up that would be uncomfortable, or confrontational,” Swick said.

“It’s weird living with somebody else, right? It’s different. I was trying to think what these things would be so we can talk about it and go ahead and get it out of the way.”

Back to jail?

Dobson is under close supervision of a parole officer, who examined the house and laid down the rules, such as no guns allowed.

“My parole officer was quite clear,” Dobson said. “He said, ‘Don’t try to put too much on your plate. Whether you know it, or feel like it, you’ve got some real adjusting to do.’ And I’m discovering as the days go by that that’s quite true.”

Dobson said prisons should do more to rehabilitate prisoners and train them for specific jobs, rather than warehouse them.

Even after prison, the statistics are stacked against ex-convicts.

An eight-year study of thousands of federal prisoners by the United States Sentencing Commission came out in 2016, showing that almost half of federal offenders released in 2005 were rearrested.

Almost one-third of the offenders were also convicted again, and one-quarter were reincarcerated, usually within two years of release.

Statistics in Dobson’s favor show that few prisoners released after age 60 go back to jail. And those with no other criminal record are most likely to stay free.

But society’s view of prison appears to be changing.

President Donald Trump is promoting more second chances for convicts and touting the bipartisan criminal justice reform of 2018, the First Step Act.

“The unemployment rate for former inmates is up to five times higher than the national average,” Trump said recently. “My administration has set an ambitious goal: We want to cut the unemployment rate for these individuals to single digits within five years. And we think there’s a really good chance of doing it.”

Kim Kardashian joined the president at the White House in June to promote new ways to help freed prisoners succeed in re-entry to society.

Swick’s hopes for her father are simple.

“I hope he gets his book published,” she said.

“And I hope he lives a long enough life to enjoy the freedom that he has now.”

Dobson recognizes that if he beats the odds against him, it will be because of his guardian angel.

“We had our moments from time to time,” he said about Rachael, “but we came through it.

“You can just imagine what it was like for her. I mean, she was all but orphaned at one point.

“We were talking about this the other night because I have made all these brave promises way back when you don’t quite know what you’re going to get into.

“But, you know, our deal was that we stay in as close touch as we can. And I get out as close to the person that she knew I was when I went in.

“That was our mission in life, right there.”

And that closes a long chapter in one of the Lowcountry’s most stunning stories.

“It is a full tale,” Dobson said.

“It’s a full tale of how low you can go, and with the good help of good people and friends, how you can get back up, too.”

Missed a chapter of Gentleman Bandit? Read it from the start here.

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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