Vermont honors the legacy of captive industry leader

Former Deputy Commissioner Leonard “Len” Crouse has passed away

Author: Vermont Captive

Montpelier, Vt. – The State of Vermont honors the legacy of Leonard “Len” Crouse after his passing on May 6, 2021. Len was appointed the first Deputy Commissioner of the then newly created Captive Insurance division in 2003 and prior to that served as the Director of Captive Insurance since 1990 for the Vermont Department of Financial Regulation (formally, the Department Banking, Insurance, Securities, and Health Care Administration). While Deputy Commissioner, Len was responsible for Vermont’s administration and regulation of captive insurance companies at a time when the industry was rapidly growing.

“Len’s significance cannot be understated and his legacy will live on within the department and the captive industry,” said Commissioner Michael Pieciak. “The number of captives licensed in Vermont tripled during Len’s time with the department and Vermont saw its highest growth when Len transitioned to the role of Deputy Commissioner.” Vermont continues to be a prominent leader in the industry, ranked first nationally and third globally with over 1200 licensed captive insurance companies to date.

Len received numerous awards for his contribution to the broader captive insurance industry, including the Captive Insurance Companies Association’s Distinguished Service Award in 2007 and in 2017 when he was inducted into the Captive Review inaugural Hall of Fame, an award which was recognized under resolution by the Vermont State Legislature that same year.

“Len made sure to greet everyone he saw. He was genuinely interested in people, and when he asked how you were doing, he sincerely wanted to know,” said Deputy Commissioner of Captive Insurance, David Provost. “He set the tone for the expectation of respect and communication that we continue to strive for today.”

“As he made his way through a captive conference or event, he became known as someone who could be tough with you on a captive issue at a meeting earlier in the day and then have a drink with you later that evening as an old friend,” said Richard Smith, President of the Vermont Captive Insurance Association. “He will sorely be missed by all who knew him.”

Len’s family has asked that donations in his name be sent to Central Vermont Home Health and Hospice in Barre, Vermont, or a Memorial Tree be planted in memory of him.

For more information on Vermont’s captive insurance industry, visit, call Brittany Nevins at 802-398-5192 or email

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