01 Being Rupert

Part One of Project Rehab
Chapter 1: Indianapolis – Being Rupert

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He could easily have been mistaken for of the countless homeless men in downtown Indianapolis. His coat is a dark green and blue hooded flannel, more suited for an Indiana spring, not the near-zero degree weather the city had been experiencing. His scraggly, salt and pepper beard is back to its unkempt state, long enough for him to grab hold of and stroke in contemplation.

His dark khaki cargo pants – not slacks, pants – were definitely work clothing, more at home on a construction site than in any office on a “casual Friday.” Underneath his jacket, a green long-sleeved shirt that would have worked for office casual clothing was unbuttoned and revealed the swirling bright colors of tie-dyed tank top. Tie-dye, his signature style.

Rupert Boneham flicked the last embers off his cigarette before heading into Punch Burger restaurant in Indianapolis. “Hey there, how are you?” his baritone voice boomed as he noticed a patron at the soda dispenser do a double-take and recognition dawn on their face. They smiled back at him, voiced a general pleasantry and headed back to their seat. “That’s Rupert,” the man told the woman at the table. “Rupert from Survivor.”

A  few feet away from wall of floor to ceiling windows and glass doors, a tie-dyed cloth is draped over a table. Short stacks of photos – some with Rupert by himself, and some with both he and his wife in tie-dye hugging on a beach familiar to the fans of Survivor lay next to several black markers. The table was festooned with copies of a paperback book, again with Rupert in tie-dye beaming at the viewer, and a small wooden chest, akin to a pirate chest.  “Support Rupert’s Kids” and “Thank You for Your Donation!” graphics were shellacked onto the chest.

0002Tonight, the restaurant was giving back to their community, by donating a quarter of their evening sales to the charity of the week for them: Rupert’s Kids. Even though the burger joint was sparsely populated, Rupert and a handful of volunteers with his mentoring program were there to greet patrons and explain the work Rupert did in turning young men and women away from the revolving door of the criminal justice system.

Later in the evening, a couple with their two small children – pre-school aged girls with their blonde hair pulled tight into pony tails – who had been sitting one table away from where Rupert was greeting patrons and autographing photos of himself – asked what the Rupert’s Kids program was.


“We work with those second, third and fourth generation young men and women,” his deep voice softened into his usual tenor range, “who are stuck in the system. They’ve never had a role model show them how to earn an honest living, or care for themselves.”

“We see girls, 13, 14 years old who want some money for themselves, and their mommas tell them ‘this check is mine – you get your own baby and you can get a check too.’” His eyes shift from the mother to the father in front of him. “They’ve never had that person who showed them to respect others, and respect themselves. They don’t know how to make a legal living, but they’ve seen their role models make an illegal one.”

Rupert explains over the next few minutes the ideas behind his program: hard work, self respect, caring for your family. All without government grant money. “We go out in grass-cutting season and cut all of the medians in Indianapolis,” he explains. “We earn the money to pay the participants, and get support from the private sector to help us keep the program working,” he explains.

A few minutes later, the husband is writing a check to Rupert’s Kids. “Thank you!” Rupert booms back into his baritone voice. He enthusiastically lays his right hand out in offer of a handshake, after the man drops the check into the treasure chest.


The traffic in the burger place is light but steady. In a few hours, Rupert has signed a couple dozen photos, and given away a few copies of his autobiography. His volunteers have set up a small web-casting space in the back part of the dining area. An orange extension cord snakes it way over to a corner out of sight of the main dining room.

Rupert sits in front of a laptop computer, waiting on Rob Cesternino, a fellow Survivor player to begin the podcast. Tonight is a reunion for three of the cast members from Rupert’s first experience on the show. He is joined by “Johnny Fairplay” and winner of the show, Sandra Diaz-Twine. He and Johnny developed a bit of animosity on the show, which they continue to play up in public appearances. Despite the cajoling and good-guy vs bad-guy reputations they have been handed by their experiences on Survivor, Rupert admits that their relationship off camera isn’t what it seems on camera.

“We help each other out,” he explains. “We’ve done appearance together, and we’ll donate items for fundraising to each other’s special projects. When we’re playing the game (the show Survivor) we’re each trying to win. Back here, though, we help each other.”

Once the podcast show is underway, Rupert grins and booms out in his baritone, often chiding Johnny or Rob. He lounges back in the restaurant’s chair, with a set of pink headphones – borrowed from his daughter – wrapped over his wild mane of wavy hair.

A few patrons, hearing his voice, wander back into the rear dining area. A large toothy smile breaks through Rupert’s beard as he spies fan using their phone to get a photo of him at the computer. Two more guys wander back, and sit at the table behind Rupert, looking over his shoulder to see the other side of the podcast video stream on the computer.

About an hour later, the restaurant manager has poked his head around the corner several times. Jessie, Rupert’s office manager, motions for him to end the podcast. A minute or two later he jumps into the online conversation to signal his impending departure.

Once he wraps, and signs off, the volunteers pack away the computer gear while Rupert thanks the store manager. One worker, a young woman is hovering with her phone out. “You want a picture?” he asks as her face lights up with a broad smile. She passes the camera phone to her manager as Rupert holds his arm wide, an invitation for the girl to come close. He hugs her, and leans in to positions his face close to hers for the photo. After the photo, he shifts to a two-armed hug, her body swallowed up in his embrace. The energy of a single hug from a fan keeps his face alight as he thanks the manager again and heads into the cold.

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