Craig Rothfeld Founder: From Finance Professional to Advocate for Justice

Sometimes the most unlikely journeys lead to the most profound purpose. When Craig Rothfeld first knocked on my door for this interview, I had no idea I was about to hear one of the most strategic comeback stories in criminal justice.

I’ve been looking forward to this conversation for months. Craig’s name keeps popping up in the most interesting places – he was recently hired as Harvey Weinstein’s prison consultant, and his client list reads like a who’s who of high-profile white collar cases. But what fascinated me most wasn’t his celebrity clients. It was how this former finance professional transformed 18 months of incarceration into a thriving business helping others navigate the exact system that once crushed him.

From Wall Street Success to Federal Investigation

Craig grew up in Oceanside, Long Island, with big plans. He started as a criminal justice major at SUNY Albany – ironically planning to become an attorney in his family’s law firm. But a phone call to his mother changed everything. She convinced him to switch to accounting, reasoning that attorneys with financial skills were rare and valuable.

That advice launched Craig into a 20-year career in financial services. He worked at Arthur Andersen, then Lehman Brothers (talk about picking winners), eventually becoming an entrepreneur. Along with his partner, he grew a 13-person trading firm into a 120-employee company generating $46 million in annual revenue.

But success bred dangerous confidence. When the 2008 financial crisis hit, instead of cutting expenses, Craig doubled down. “Rather than being conservative and retrenching, we viewed this as an opportunity because so many people gotten laid off to get like a once in a generational talent,” he told me. The problem was their expenses grew at the same rate as their ambitions, and when trading volume plummeted, they faced a regulatory capital nightmare.

The 13-Month Nightmare Before Prison

What Craig did next haunts every entrepreneur who’s ever faced a cash flow crisis. He borrowed against receivables to maintain regulatory capital requirements, then signed compliance reports knowing the numbers were false. “The thought process was by the time they figure it out if they ever figure it out, we’ll have fixed it. It’ll be a slap on the wrist.”

He was catastrophically wrong.

The business shut down in 2011. Craig took a regulatory bar from the industry, thinking his legal troubles were over. Then came 13 months of pure hell – knowing Manhattan DA’s office was investigating but not knowing when the hammer would fall. “You wake up every day wondering is it gonna happen today? Is it gonna happen? When’s it gonna happen?” Those 13 months of uncertainty, Craig says, were worse than the actual 18 months he ultimately served.

From Rikers Island to Prison Consultant

The knock came February 6, 2014. Craig spent his first five weeks at Rikers Island – a brutal introduction that nearly broke him. He found himself in a 60-man dorm where 41 inmates were Bloods gang members who initially suspected he was an undercover cop.

But something remarkable happened. Craig kept his head down, helped illiterate inmates read their legal papers, shared his books, and gradually earned respect. “The reality is it’s a miracle that no one ever laid a hand on me, that I never got punched, and no guard ever… it’s an absolute miracle,” he reflected.

After Rikers, Craig moved through New York’s prison system – Ulster reception facility, then Ogdensburg near the Canadian border, finally landing in work release programs that eased his transition home. Throughout his incarceration, he maintained rigid routines, read 51 books, and most importantly, never stopped visualizing his comeback.

Building Inside Out From the Ground Up

Three weeks after his release in June 2017, Craig got the call that changed everything. His former defense attorney Mark McNutt suggested he become a prison consultant, and federal consultant Joel Sickler offered him his first case. But Craig refused to wing it. He enrolled in a criminal sentencing certification program at John Jay College, eventually earning a master’s degree while building his practice.

“I didn’t want to just tell people, ‘Look, I went to prison for 18 months, I’m an expert, hire me,’” Craig explained. He wanted legitimate credentials to match his lived experience.

The strategy worked. By 2020, when attorney Arthur Aidala brought him onto the Harvey Weinstein case, Craig had built Inside Out into one of the most respected prison consulting firms in New York. Today, he guides clients and their families through every phase of the criminal justice process, from plea negotiations to sentencing to reentry planning.

What strikes me most about Craig’s story isn’t just the comeback – it’s the methodical way he rebuilt. He used mentors, invested in education, started small, and let his work speak for itself. He coupled 22 months of defending himself and 18 months of incarceration to become an expert on the New York State Department of Corrections. Now he devotes his life to guiding others through the same system that once seemed designed to destroy him.

That’s not just a business model. That’s turning your deepest nightmare into someone else’s lifeline.