Craig Rothfeld

Craig Rothfeld
Occupation	Prison consultant
Known for	Federal prison consulting for high-profile clients
Education	New York University Stern School of Business
Alma mater	University at Albany, SUNY; New York University Stern School of Business
Website	insideoutsideltd.com

Craig Rothfeld is an American prison consultant and former securities industry executive who founded Inside Outside Ltd., a firm that advises individuals facing federal incarceration on how to prepare for prison life and plan for reentry into society. A former executive at WJB Capital Group, a New York–based brokerage that collapsed amid allegations of financial fraud, Rothfeld himself served a federal prison sentence for financial crimes before pivoting to a second career advising others navigating the criminal justice system. His client roster has included some of the most prominent figures in American criminal proceedings, among them Harvey Weinstein, Luigi Mangione, and Keith Raniere. Rothfeld's work has drawn significant media attention for illuminating the growing field of prison consulting, in which former inmates leverage their firsthand experience to counsel newly sentenced defendants on the practical, psychological, and logistical realities of incarceration.

Early Life and Education

Craig Rothfeld attended the University at Albany, SUNY, where he completed his undergraduate studies. He subsequently enrolled at the New York University Stern School of Business, one of the leading business schools in the United States, where he pursued graduate-level education in business and finance. His academic background in finance provided the foundation for a career on Wall Street that would span more than a decade before his legal troubles.

Career

Securities Industry and WJB Capital Group

Before entering the prison consulting field, Rothfeld worked as an executive in the securities industry. He was associated with WJB Capital Group Inc., a New York–based brokerage firm that operated on the floor of the New York Stock Exchange. WJB Capital was a small but active brokerage that executed trades for institutional and retail clients.

The firm encountered severe financial difficulties in the early 2010s. In January 2012, WJB Capital ceased operations, unable to raise sufficient capital to continue its business. The closure was reported by The New York Times DealBook, which noted that the small brokerage had called it quits after failing to secure the funding necessary to sustain its operations. Around the same time, Bloomberg News reported that WJB Capital Group had been sued for alleged fraud.

In February 2014, former executives of the brokerage were charged with fraud. The New York Times DealBook reported that ex-brokerage executives faced charges related to deceptive practices at the firm. Traders Magazine reported that WJB Capital executives had been charged in a plan to prop up the brokerage by concealing its financial distress. The Financial Industry Regulatory Authority (FINRA) subsequently alleged that WJB Capital Group and two of its top executives had hidden the company's financial difficulties for years and traded securities in violation of regulatory requirements.

The Manhattan District Attorney's Office included information pertaining to the WJB Capital prosecution in its 2015 annual report. Rothfeld's registration history with FINRA is documented in the organization's BrokerCheck database.

As a result of the legal proceedings stemming from the firm's collapse and the fraud charges, Rothfeld served a federal prison sentence. This period of incarceration would prove formative, providing him with the direct personal experience that later became the basis for his consulting practice.

Transition to Prison Consulting

Following his release from federal prison, Rothfeld founded Inside Outside Ltd., a prison consulting firm, in approximately 2014. The firm offers services designed to help individuals who have been sentenced to prison—or who anticipate such a sentence—prepare for the experience of incarceration. Services typically include guidance on what to expect in prison, advice on how to interact with other inmates and corrections officers, preparation for the physical and psychological challenges of confinement, and planning for eventual release and reintegration into society.

Rothfeld's transition from convicted financial executive to prison consultant is part of a broader trend in which individuals with firsthand experience of incarceration offer their knowledge to others facing similar circumstances. The prison consulting industry has grown in the United States as the federal criminal justice system has expanded, and as high-profile white-collar and celebrity defendants have increasingly sought professional guidance before surrendering to authorities.

High-Profile Clients

Harvey Weinstein

Rothfeld's most publicly documented client relationship has been with Harvey Weinstein, the former film producer convicted of sex crimes in New York in February 2020 and subsequently sentenced to prison. The New York Times reported in March 2020 that Rothfeld had been retained as Weinstein's prison consultant, drawing on his own experience in both the federal prison system and his familiarity with Rikers Island, New York City's main jail complex. Financial Planning magazine noted the unusual trajectory of Rothfeld's career, from broker-dealer executive to prison adviser for one of the most high-profile defendants in recent American history.

Rothfeld's role with Weinstein extended beyond initial preparation for incarceration. The Hollywood Reporter published an exclusive account in April 2025 describing Weinstein's life behind bars in detail, noting that the former producer spent approximately 23 hours per day alone in his prison cell. The report indicated that Weinstein continued to manage aspects of his affairs from inside, and Rothfeld remained involved as an adviser throughout Weinstein's ongoing legal proceedings.

In early 2026, Weinstein was rushed from Rikers Island to Bellevue Hospital for emergency heart surgery after experiencing chest pains, an event that further highlighted the health challenges facing incarcerated individuals and the ongoing need for outside advisers to coordinate on their behalf. Articles in the New York Daily News have also referenced Rothfeld in the context of Weinstein's incarceration.

The inkl news aggregator described Rothfeld as emblematic of a growing trend among high-profile defendants who seek specialized guidance for surviving jail, calling attention to the expanding role of prison consultants in the American legal landscape.

Luigi Mangione

In 2025, Rothfeld was retained by Luigi Mangione, who was charged in the shooting death of UnitedHealthcare CEO Brian Thompson in December 2024. Fox News reported that Mangione had hired Rothfeld, who was already known for his work with Weinstein, to serve as his prison consultant. The South China Morning Post profiled Rothfeld in the context of the Mangione case, describing his background and the range of services he provides to high-profile defendants.

LA Magazine reported on Mangione's legal defense strategy in December 2025, noting a high-stakes effort to suppress key evidence, including a gun, silencer, and notes linked to the crime. While the article focused on legal strategy, Rothfeld's involvement as Mangione's prison consultant was part of the broader defense team's efforts to manage the defendant's situation during pretrial incarceration.

Keith Raniere

The South China Morning Post also reported that Rothfeld served as a prison consultant to Keith Raniere, the founder of NXIVM who was convicted in 2019 on charges including sex trafficking, racketeering, and forced labor. Details regarding the scope and nature of Rothfeld's work with Raniere have not been as extensively documented as his work with Weinstein and Mangione.

Allen Weisselberg

Rothfeld was also linked to the case of Allen Weisselberg, the former chief financial officer of the Trump Organization. Business Insider reported in November 2022 that Weinstein's prison coach was observed following developments in the Trump Organization trial. In January 2023, when Weisselberg began his sentence at Rikers Island following his guilty plea to tax fraud charges, Business Insider and Reuters reported on his preparation for incarceration, a context in which Rothfeld's services were referenced.

Media Appearances and Public Speaking

Rothfeld has been featured in numerous media outlets discussing the prison consulting profession and the realities of incarceration. NBC News produced a segment in October 2025 in which correspondent Chloe Melas visited Rothfeld to document how he prepares high-profile inmates for lockup. The segment provided a detailed look at his methods, the advice he offers clients, and the practical logistics of entering the prison system.

In October 2023, the Kings County Criminal Bar Association (KCCBA) hosted a seminar on sentencing that featured Rothfeld as an expert speaker. The Brooklyn Eagle covered the event, noting Rothfeld's expertise in advising individuals on the sentencing process and what follows after a conviction.

Rothfeld has also participated in the White Collar Support Group® speaker series, a program designed for individuals involved in or affected by white-collar criminal proceedings. In March 2026, he appeared alongside fellow prison consultant Sam Mangel to discuss their work and offer insights into the prison consulting process.

His commentary on incarceration-related matters has appeared in publications including The New York Times, Business Insider, Reuters, The Hollywood Reporter, Financial Planning, and Above the Law, among others.

Personal Life

Rothfeld is based in the New York metropolitan area. He has spoken publicly about how his own experience of incarceration shaped his understanding of the criminal justice system and motivated his career shift from finance to prison consulting. Beyond these publicly documented facts, Rothfeld has maintained a relatively private personal life.

Recognition

Rothfeld's prominence in the prison consulting field stems primarily from the high-profile nature of his clients and the extensive media coverage his work has generated. His retention by Harvey Weinstein in 2020 brought national attention both to Rothfeld personally and to the prison consulting profession more broadly. The subsequent addition of clients such as Luigi Mangione and Keith Raniere further elevated his public profile.

Legal and criminal justice professionals have recognized Rothfeld as a knowledgeable practitioner in the niche field of incarceration preparation. His invitation to speak at the Kings County Criminal Bar Association seminar on sentencing in 2023 reflected his standing among criminal defense attorneys as a resource on post-conviction issues. His participation in the White Collar Support Group® speaker series similarly indicates recognition within the community of professionals who work with white-collar defendants.

The Above the Law legal blog examined the broader question of whether prison consultants provide meaningful value to clients, using Rothfeld's work with Weinstein as a case study. The article explored the practical and psychological benefits such consultants offer, including advice on facility selection (where applicable), daily routines, commissary management, and interpersonal dynamics within prison environments.

Legacy

As one of the most publicly visible prison consultants in the United States, Rothfeld's career trajectory—from Wall Street executive to federal inmate to incarceration adviser—illustrates the emergence and professionalization of prison consulting as a recognized service within the American criminal justice ecosystem. The field, while still relatively small, has grown as federal and state prosecution of white-collar crime, public corruption, and high-profile criminal cases has increased public awareness of the challenges associated with incarceration.

Rothfeld's work has contributed to public understanding of the realities of prison life through his media appearances and his willingness to discuss, in specific terms, the conditions inmates face in facilities ranging from federal prisons to Rikers Island. His accounts of advising Harvey Weinstein, in particular, provided the public with detailed information about conditions at one of the most notorious jail complexes in the United States.

The attention generated by Rothfeld's high-profile engagements has also raised questions about equity in the criminal justice system, as prison consulting services are generally available only to defendants with the financial resources to retain such advisers. This disparity has been noted in media coverage, though Rothfeld himself has framed his services as filling a genuine informational gap for individuals entering an unfamiliar and often dangerous environment.