The incredible story of a slave who stole a boat, sailed to freedom, and became a hero.

On May 13, 1862, Robert Smalls donned a straw hat, hoisted a Confederate flag over a warship, and piloted himself to freedom.

Yeah, seriously.

At 22, Robert Smalls was working in servitude for the Confederacy. Desperate for deliverance, the young man planned an extraordinary and daring escape, and when an opportunity presented itself, he risked life and limb to free himself and 16 others.


This is the story of Smalls, and 10 reasons he's still the stuff of legends over 150 years later.

A drawing of Robert Smalls. Image via Harper's Weekly/Wikimedia Commons.

1. He planned the escape for more than a year.

Born a slave in Beaufort, South Carolina, Smalls was brought to Charleston at 12 to be rented out for work. There, he met his wife, Hannah, who was a slave for a local family. While the family allowed Robert, Hannah, and their children to live together, the agreement wasn't binding. Robert wanted to purchase his family outright but didn't have the $800 the deal required.

Running was their best option. He was a skilled sailor, so an escape on the water was Smalls' perfect plan. He told his family to wait patiently for just the right moment.

The house in Beaufort, South Carolina, where Smalls was born. Photo via Historic American Buildings Survey/Wikimedia Commons.

2. Just before dawn on May 13, 1862, Smalls took his chance.

Smalls worked on the CSS Planter, a steamer warship. The Planter was docked for the night in the Charleston Harbor. The vessel was set to go back out the next day, so it was filled with supplies and weapons. The ship's captain, Capt. C.J. Relyea, and its white crew members decided to go to shore for the night, leaving Smalls and a few other slaves behind.

This was his window of opportunity.

GIF via "Drunk History"/Comedy Central.

3. But first, he had to make a pit stop.

To avoid suspicion, Smalls put on Relyea's hat and ordered the crew to raise the Confederate flag. The boat made a quick stop at a nearby wharf to pick up his family along with a few other women and children seeking their freedom.

Image via PBS/YouTube.

4. Not everyone could pull off piloting the large vessel, but this wasn't Smalls' first rodeo ... er, boat show.

Smalls had worked on the Planter for years and had the skills of a captain, but his skin color had kept him from earning the title. Instead, he was the boat's wheelman but spent hours each day watching Relyea at work, time that would prove especially useful.

Image via PBS/YouTube.

5. Piloting the ship wasn't the only challenge; Smalls and the crew had to pass four Confederate check points.

Sweating yet?

Wearing Relyea's hat and jacket, Smalls strolled along the ship's deck, mimicking the captain's gait. And from watching in the past, he knew just the signals he'd have to give to pass each fort.


GIF via "Drunk History"/Comedy Central.

6. The fourth checkpoint, Fort Sumter, was the grandaddy of checkpoints. And that grandaddy had guns. Lots and lots of guns.

The other slaves on board told Smalls not to get so close; after all, the sun was coming up. But pivoting, even a little, would surely arouse suspicion. Smalls held fast and gave the signal.

A few seconds later, the Confederate soldiers at the fort signaled back: They were free to pass.

GIF via PBS/YouTube.

7. Though he made it past Fort Sumter, Smalls wasn't out of danger.

After all, he was still in a Confederate ship quickly headed toward Union waters.


GIF via "Ghost."

With help from his wife, Smalls raised a white bed sheet for a flag. Luckily, Union soldiers spotted it in time and boarded the ship.

He saluted and delivered the Planter (and its cache of Confederate weapons) to the Union troops.

Smalls and his 16 passengers were finally free.

8. For his cunning and bravery, Congress passed a bill authorizing the Navy to pay for the CSS Planter and awarded Smalls some much-needed funds.

Smalls received $1,500 for the ship and supplies and was able to start life as a free man and a hero.

Image via PBS/YouTube.

9. Smalls went on to help enlist thousands of black soldiers for the Union.

Thanks to his newfound celebrity, Smalls met with Abraham Lincoln to encourage the president to allow black soldiers to enlist for the Union and recruited 5,000 men for the effort. He also served, piloting the Planter during several intense military actions, and became one of the highest-paid black soldiers of the Civil War era.

One of the many black soldiers who fought for the Union, thanks to Smalls' efforts. Image via Beinecke Rare Book & Manuscript Library/Wikimedia Commons.

10. After the war, he went on to serve in the South Carolina state legislature and the U.S. House of Representatives.

His was a life full of service and fierce loyalty to the country that liberated him. Smalls was also a champion for the civil rights of African-Americans.

"My race needs no special defense for the past history of them and this country," he once said. "It proves them to be equal of any people anywhere. All they need is an equal chance in the battle of life."

Smalls years after his daring escape. Image via Library of Congress.

Smalls did many amazing things in the battle of life.

For his final act, he lived well into his 70s and died in the home where he was born a slave, which he'd purchased from his former owner.

The Robert Smalls House became a National Historic Landmark in 1974.

The Robert Smalls House in Beaufort, South Carolina. Photo by Elisa.Rolle/Wikimedia Commons.

Want more? See an animated reenactment of Smalls' daring escape.

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Judy Vaughan has spent most of her life helping other women, first as the director of House of Ruth, a safe haven for homeless families in East Los Angeles, and later as the Project Coordinator for Women for Guatemala, a solidarity organization committed to raising awareness about human rights abuses.

But in 1996, she decided to take things a step further. A house became available in the mid-Wilshire area of Los Angeles and she was offered the opportunity to use it to help other women and children. So, in partnership with a group of 13 people who she knew from her years of activism, she decided to make it a transitional residence program for homeless women and their children. They called the program Alexandria House.

"I had learned from House of Ruth that families who are homeless are often isolated from the surrounding community," Judy says. "So we decided that as part of our mission, we would also be a neighborhood center and offer a number of resources and programs, including an after-school program and ESL classes."

She also decided that, unlike many other shelters in Los Angeles, she would accept mothers with their teenage boys.

"There are very few in Los Angeles [that do] due to what are considered liability issues," Judy explains. "Given the fact that there are (conservatively) 56,000 homeless people and only about 11,000 shelter beds on any one night, agencies can be selective on who they take."

Their Board of Directors had already determined that they should take families that would have difficulties finding a place. Some of these challenges include families with more than two children, immigrant families without legal documents, moms who are pregnant with other small children, families with a member who has a disability [and] families with service dogs.

"Being separated from your son or sons, especially in the early teen years, just adds to the stress that moms who are unhoused are already experiencing," Judy says.

"We were determined to offer women with teenage boys another choice."

Courtesy of Judy Vaughan

Alexandria House also doesn't kick boys out when they turn 18. For example, Judy says they currently have a mom with two daughters (21 and 2) and a son who just turned 18. The family had struggled to find a shelter that would take them all together, and once they found Alexandria House, they worried the boy would be kicked out on his 18th birthday. But, says Judy, "we were not going to ask him to leave because of his age."

Homelessness is a big issue in Los Angeles. "[It] is considered the homeless capital of the United States," Judy says. "The numbers have not changed significantly since 1984 when I was working at the House of Ruth." The COVID-19 pandemic has only compounded the problem. According to Los Angeles Homeless Services Authority (LAHSA), over 66,000 people in the greater Los Angeles area were experiencing homelessness in 2020, representing a rise of 12.7% compared with the year before.

Each woman who comes to Alexandria House has her own unique story, but some common reasons for ending up homeless include fleeing from a domestic violence or human trafficking situation, aging out of foster care and having no place to go, being priced out of an apartment, losing a job, or experiencing a family emergency with no 'cushion' to pay the rent.

"Homelessness is not a definition; it is a situation that a person finds themselves in, and in fact, it can happen to almost anyone. There are many practices and policies that make it almost impossible to break out of poverty and move out of homelessness."

And that's why Alexandria House exists: to help them move out of it. How long that takes depends on the woman, but according to Judy, families stay an average of 10 months. During that time, the women meet with support staff to identify needs and goals and put a plan of action in place.

A number of services are provided, including free childcare, programs and mentoring for school-age children, free mental health counseling, financial literacy classes and a savings program. They have also started Step Up Sisterhood LA, an entrepreneurial program to support women's dreams of starting their own businesses. "We serve as a support system for as long as a family would like," Judy says, even after they have moved on.

And so far, the program is a resounding success.

92 percent of the 200 families who stayed at Alexandria House have found financial stability and permanent housing — not becoming homeless again.

Since founding Alexandria House 25 years ago, Judy has never lost sight of her mission to join with others and create a vision of a more just society and community. That is why she is one of Tory Burch's Empowered Women this year — and the donation she receives as a nominee will go to Alexandria House and will help grow the new Start-up Sisterhood LA program.

"Alexandria House is such an important part of my life," says Judy. "It has been amazing to watch the children grow up and the moms recreate their lives for themselves and for their families. I have witnessed resiliency, courage, and heroic acts of generosity."

via Wikimedia Commons and Goalsetter

America's ethnic wealth gap is a multi-faceted problem that would take dramatic action, on multiple fronts, to overcome. One of the ways to help communities improve their economic well-being is through financial literacy.

Investopedia says there are five primary sources of financial education—families, high school, college, employers, and the military — and that education and household income are two of the biggest factors in predicting whether someone has a high level of financial literacy.

New Orleans Saints safety, two-time Super Bowl Champion, and social justice activist Malcolm Jenkins and The Malcolm Jenkins Foundation hope to help bridge the wealth gap by teaching students about investing at a young age.

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2020 was difficult (to say the least). The year was full of life changes, losses, and lessons as we learned to navigate the "new normal." You may have questions about what the changes and challenges of 2020 mean for your taxes. That's where TurboTax Live comes in, making it easy to connect with real tax experts to help with your taxes – or even do them for you, start to finish.

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Julz, hairdresser and salon owner

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She was also without a job for most of 2020 and struggled to find something new.

So, Alana took it as a sign: she decided to launch her own business so she could support her new baby, and that's exactly what she did. She started a feel-good company that specializes in creating affirmation card decks — and she's currently in the process of starting a second, video-editing business.

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"I got my mom a plane ticket to finally [have her] meet [my daughter] for her first birthday," Alana says. "I was also able to get a new computer," which helped her invest in her new business and work on her video editing skills. "It's helped my family and me so much," she says.


Michael, science teacher

When schools shut down across the country last year, Michael had to learn how to adapt to a virtual classroom.

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Ricky, motivational youth speaker

As a motivational speaker, Ricky was used to doing his job in person, but, he says, "when COVID-19 hit, it altered my ability to travel and visit schools in person [because] schools moved to fully virtual or hybrid models."

He knew he had to pivot — so he began offering small virtual group workshops for student leadership groups at middle and high schools.

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"[It] has been a major blessing," he says "There will be multiple schools and student groups from across the country that I can hold leadership workshops with to empower them with the tools to be inspirational leaders in their school, community, and world."

Plus, he says, it was great knowing he had an expert to help him figure out how being remote affected his taxes. "I felt confident and assured in the process of filing my taxes knowing I had an expert working with me, says Ricky. "There were things my expert knew that I would not have considered when filing on my own."

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