Full Name
Daniel Hickey
Job Title
CEO
Company
Roosevelt Road Specialty
Speaker Bio
Daniel Hickey Jr. is the founding partner and CEO of Roosevelt Road Capital Partners (RRCP), a global insurance organization that wholly owns Tradesman Program Managers, K&B Specialty Insurance, Renaissance Specialty Insurance, and Roosevelt Road Re, a dedicated MGU and Class 3B Bermuda-reinsurance company.
Under his leadership, RRCP has grown premiums in excess of $1.3 billion, establishing itself as an industry leader in delivering best-in-class claims and loss control services to construction, property, sports, leisure and entertainment, senior and assisted living and business auto sectors - all with exceptional underwriting results.
In 2016, with a visionary approach, recognizing and seizing the opportunity created by the dislocation in the New York construction market, Mr. Hickey founded Tradesman Program Managers (TPM) – a managing general agent specializing in contractors’ commercial general liability.
Staffed by experts who specialize in detecting fraud, TPM launched a deep investigation in 2021 into fraudulent injury claims in the greater New York construction market uncovering a troubling pattern: staged accidents, undocumented workers filing multiple claims and suspiciously identical injury reports, all linked to coordinated efforts by plaintiff attorneys and medical providers. TPM filed five federal racketeering lawsuits against dozens of lawyers and doctors. The initiative attracted attention from insurers around the country and from national media outlets such as the ABC News, Inside Edition, and the New York Post.
In 2025, the Insurance Insider presented Roosevelt Road Specialty and Tradesman Program Managers with the award for Casualty Underwriting Team of the Year.
Mr. Hickey’s strategic insight and leadership have positioned him as a forward-thinking authority within the industry. He continues to break the mold by investing in technology not only for the company’s underwriting and claims teams, but also for insureds themselves, understanding that an insured’s best protection against a fraudulent injury claim is the use of technology, like AI dash cams and cutting-edge field management software.
Prior to founding RRCP, Mr. Hickey served as chairman and CEO of Majestic Holdings, LLC and led the company to a successful public offering in 2005. He succeeded in turning Majestic Insurance Company, a B++ company, into an A- “AM Best”-rated company and grew premiums from $50 million to more than $150 million and expanded the business into four states.
With a comprehensive understanding of the insurance model from top to bottom, Mr. Hickey possesses a rare ability to integrate and align key business disciplines, building and executing effective corporate strategies with precision and foresight.
Mr. Hickey received his B.A. in Business Administration from Northeastern University where he graduated cum laude.
Under his leadership, RRCP has grown premiums in excess of $1.3 billion, establishing itself as an industry leader in delivering best-in-class claims and loss control services to construction, property, sports, leisure and entertainment, senior and assisted living and business auto sectors - all with exceptional underwriting results.
In 2016, with a visionary approach, recognizing and seizing the opportunity created by the dislocation in the New York construction market, Mr. Hickey founded Tradesman Program Managers (TPM) – a managing general agent specializing in contractors’ commercial general liability.
Staffed by experts who specialize in detecting fraud, TPM launched a deep investigation in 2021 into fraudulent injury claims in the greater New York construction market uncovering a troubling pattern: staged accidents, undocumented workers filing multiple claims and suspiciously identical injury reports, all linked to coordinated efforts by plaintiff attorneys and medical providers. TPM filed five federal racketeering lawsuits against dozens of lawyers and doctors. The initiative attracted attention from insurers around the country and from national media outlets such as the ABC News, Inside Edition, and the New York Post.
In 2025, the Insurance Insider presented Roosevelt Road Specialty and Tradesman Program Managers with the award for Casualty Underwriting Team of the Year.
Mr. Hickey’s strategic insight and leadership have positioned him as a forward-thinking authority within the industry. He continues to break the mold by investing in technology not only for the company’s underwriting and claims teams, but also for insureds themselves, understanding that an insured’s best protection against a fraudulent injury claim is the use of technology, like AI dash cams and cutting-edge field management software.
Prior to founding RRCP, Mr. Hickey served as chairman and CEO of Majestic Holdings, LLC and led the company to a successful public offering in 2005. He succeeded in turning Majestic Insurance Company, a B++ company, into an A- “AM Best”-rated company and grew premiums from $50 million to more than $150 million and expanded the business into four states.
With a comprehensive understanding of the insurance model from top to bottom, Mr. Hickey possesses a rare ability to integrate and align key business disciplines, building and executing effective corporate strategies with precision and foresight.
Mr. Hickey received his B.A. in Business Administration from Northeastern University where he graduated cum laude.
