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Human Interest

The Improbable Life of Wes Moore, the New CEO of The Robin Hood Foundation: ‘We Are Not Promised Anything’

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Wes Moore
Creative Production Agency: Kworq

When Wes Moore was named chief executive of the Robin Hood Foundation, a top NYC poverty-fighting nonprofit that’s a favorite of Wall Street titans and A-list celebrities, it marked the latest chapter in his amazing life story.

“My life is a collection of two steps forward and one step back,” the 38-year-old tells PEOPLE.

Recently, Moore, a best-selling author, combat veteran, entrepreneur (and a 2001 PEOPLE top bachelor), shared some key moments of his life during a break in modeling suits for the menswear company Hickey Freeman‘s ad campaign to encourage businesses to hire veterans.

“I started understanding consequences,” Moore says.

After his father, a TV reporter, died of a misdiagnosed virus when Moore was just 3 years old, his mother, Joy, moved the family from Baltimore to a rough Bronx, New York, neighborhood to be with her family.

Wes started to hang out with a drug-dealing friend, skipped classes and had run-ins with cops. 

“The first time I had handcuffs on my wrists was when I was 11,” he says of his arrest for vandalism and loitering in a drug-free zone. There would be two more arrests. 

“I was spending a lot of time hurting people that loved me,” says Moore, “trying to impress people who could care less about me.”

Wes Moore
Creative Production Agency: Kworq

When Moore was 13, Joy sent him to boarding school at Pennsylvania’s Valley Forge Military Academy to improve his grades and attitude. He didn’t want to go.

“She packed up the car and threw me in, and I thought she was kidding at first,” he says. “She had been threatening me with this for years.” 

At school Moore’s troubles continued. He was in the process of getting kicked out when he befriended a cadet who became a mentor. 

That guidance, coupled with help from other mentors who became like family, enabled him to soar. “At some point, what I began to understand is that my life had a relevance to someone other than just me,” he says.

Moore excelled academically, and won a Rhodes Scholarship as a senior at Johns Hopkins University in Baltimore.

During that year, another young man named Wes Moore from a rough Baltimore neighborhood was charged with murdering an off-duty police officer in a February 2000 shootout.

After this “other” Wes Moore was convicted of murder and sentenced to life without parole, Moore tracked him down. 

The pair struck up a friendship that Moore details in the 2010 New York Times bestselling memoir, The Other Wes Moore, about how two men from similar tough urban neighborhoods can end up with such different lives.

Moore continues to stay in contact with “the other” Wes Moore, who is serving out his sentence in a Maryland prison. 

“He helps remind me every time I see him about life’s impermanence,” Moore says. “We are not promised anything — in a moment’s notice things can change by the decisions that we make.”

After Moore earned a master’s degree in international relations from Oxford as a Rhodes Scholar in 2004, he decided to enter the military as a paratrooper and captain in the United States Army, with a combat tour in Afghanistan.

His empathizes with the struggles he sees some veterans face when returning from war.

“Oftentimes the narrative is that returning veterans are some kind of charity who need help,” says Moore, “but the (Hickey Freeman) ad campaign is saying no, they are assets who need to be unleashed.”

Wes Moore
Creative Production Agency: Kworq

The campaign was inspired by Jacob Sipple, a Marine corps veteran who served in Afghanistan and is the made-to-measure cutting and project supervisor at Hickey Freeman. As part of the campaign, Hickey Freeman will donate suits to veterans transitioning to civilian jobs. 

Sipple is part of the campaign, along with Joe Cardona, an active duty US Naval Officer and New England Patriots long snapper, and Jake Wood, a former Marine sniper who is now CEO of Team Rubicon, a veteran-led disaster response organization.

After Moore left the military, he founded BridgeEdU, an organization that helps students get to college and stay enrolled.

Moore says that growing up amidst poverty continues to shape his view on helping the poor. As CEO of the Robin Hood Foundation, he is now at the helm of NYC’s largest poverty-fighting organization, which funds schools, health care providers, food pantries and other programs.

“I feel you will never be able to separate me from where I came from,” he says, “and you’ll never be able to separate me from my experiences.”