Simjay Kapoor

Age: 27

Role: World-class bullshitter, know-it-all, and laundry guru

Who I’d Cast: Karan Soni

Simjay has served three years in San Judas for fraud. In prison, he does the inmates’ laundry, but his greatest talent is his ability to talk his way out of anything.

Wickedly smart and too arrogant for his own good, Simjay dropped out of Stanford at the tender age of nineteen — much to the chagrin of his parents. With an engineer father and brain surgeon mother, Simjay was destined to receive his Ph.D., but he had a much more grandiose plan.

With two thousands dollars and an off-the-rack suit, Simjay used his Spanish, Italian, and Mandarin to con his way across five continents. He worked when he needed money — qualifications be damned — and posed as a tour guide, a gondolier, and once even a sherpa.

Finally, Simjay made his way back to the states and set up shop as a New Age guru in Southern California. He built an enormous following promising life-changing results to those who committed their life to his ways and agreed to give up all their worldly possessions. With the tuition he collected from his first 500 followers, Simjay bought 200 acres of land and turned it into Quest Ranch — a “retreat for the spiritually rich,” where he extolled the virtues of humility, charity, introspection, and simplicity.

For years he persuaded his wealthy disciples to auction off their Birkin bags, Aston Martins, and vacation homes to cleanse their souls, but instead of donating the money to charity as he promised, Simjay sold off their possessions and kept the proceeds for himself.

Eventually, the feds got involved, and Simjay was sentenced to eight years in prison. He accepted a place at San Judas and used his B.S.-ing skills to earn the favor of Hudson Peters, leader of the men’s colony. Inside, Simjay spends most of his time telling other people how things should be done (his nickname is “Google”) and brainstorming ways to trade his smarts for extra rations.