Rory McMahon has built a remarkable career as a probation officer, private investigator, teacher, and author, spanning over 50 years. He began his professional journey after attending St. Joseph’s in Bronxville, and went on to work in Westchester County and other regions across the U.S., including federal assignments in Florida. Mr. McMahon has dedicated his life to public service, investigation, and education, and he was willing to share insights and advice about his career with students.
Mr. McMahon began his career as a probation officer in 1973. After being an English major in college, he struggled to find a job as an English teacher because many graduates wanted to become teachers to avoid the draft. That is when Daniel F. McMahon, supreme court judge, suggested becoming a government worker. Once he became a parole officer, he faced dangerous situations early on, including assignments in Harlem shortly after another officer had been killed. Despite lacking formal safety training and being unarmed, he navigated these risks with guidance from experienced coworkers. Mr. McMahon believes this experience is why he is a big advocate for proper safety and defense training for officers and government workers. When asked what inspired him to pursue a career in private investigation, he said that after leaving government service he knew he wanted to teach, but he also wanted to be able to apply his investigative skills. This led him to earn his private investigator license, develop his own curriculum for PI courses, and eventually write the textbook Practical Handbook for Professional Investigators, now in its third edition.
The most rewarding aspect of Mr. McMahon’s work, he says, is “helping people and seeing a noticeable change.” Across his careers as a probation officer, private investigator, and teacher, his focus has always been on serving the community, protecting clients, and giving a voice to those navigating difficult circumstances. He recalls working on a federal case resulting in not-guilty acquittals and considers that outcome among the highlights of his career, because it reminds him why he loves his job.
The notable case was the “Liberty City 7,” in which seven Haitian men were wrongfully accused of supporting Al-Qaeda. Two trials ended in mistrials, but a third resulted in the conviction of Patrick Abraham, the defendant he represented, also a man that Mr. McMahon strongly believes was innocent. After Patrick Abraham served his sentence, he was then deported back to Haiti, this was upsetting to Mr. McMahon because not only was he an innocent man, he knew how much Abraham disliked Hatia. It was also upsetting to tax payers because so much money was spent on the three trials and imprisoning him, it seemed as though it was a wasted effort if he was going to be sent back to Haiti anyway. Specifically due to the fact that Abraham had never heard of the terrorist group. This miscarrage of justice led Mr. McMahon to reflect on the case, he says it was a formative experience that reinforced the importance of thorough investigation, careful analysis, and ethical responsibility.
One of the more challenging aspects of his work was running his own private investigation agency, between 1978–1990. He was responsible for marketing, client relations, and managing all aspects of the business on his own, and he admits he dislikes dealing with paperwork, when he prefers to be working with people and influencing positive change. McMahon also dealt with emotionally difficult cases, such as matrimonial investigations, and faced dangerous encounters involving organized crime, drug dealers, and unsafe neighborhoods. He recalls one incident where a suspect threw a sledgehammer at him, and another where a car became stuck over an open manhole during surveillance. Yet despite the dangers and obstacles, he says the work was always worth it.
Beyond his work as an investigator, Mr. McMahon has made significant contributions as an educator and author. He created one of the only structured private investigation training programs in the U.S., converting it to digital form during the pandemic to ensure students could continue learning. He emphasizes that investigative skills are not only essential for private investigators but also valuable in many professions. On writing, he notes that “it isn’t a trainable skill, but you can be educated,” encouraging students to pursue their passions in storytelling with dedication and curiosity.
This year, Mr. McMahon reached another impressive milestone when he published his book Fort Apache (2025), which explains the high-stakes world of organized crime and law enforcement through his firsthand experiences as a federal probation officer and private investigator. The book follows notorious figures like Ben “Darth Vader” Kramer, a drug smuggler and powerboat racer, and also highlights lesser-known criminals, such as Hilmer Sandini. Using knowledge and recalling experiences from decades of high-risk assignments in New York and South Florida, McMahon offers a rare insider perspective on the “gray areas” of crime, where morality, justice, and survival intersect. Fort Apache delivers a compelling look at crime, investigation, and the ethical challenges of pursuing justice.
When asked if he would choose the same career path again, Mr. McMahon said he absolutely would. Despite the challenges, he feels fortunate to have worked on meaningful cases, helped countless clients, and mentored students in investigative work. His story demonstrates that a career in investigation, public service, and education is not only about skill but also about commitment, integrity, and making a positive impact on the lives of others.
Mr. McMahon’s career serves as an inspiring example of dedication, resilience, and passion. From dangerous assignments as a probation officer to shaping the next generation of private investigators through teaching and writing, his journey highlights the rewards of a career built on service, investigation, and lifelong learning.
