Biography
The American Legion Department of Florida
Commander Michael “Gambler” Raymond
Department Commander Michael “Gambler” Raymond
Michael A. “Gambler” Raymond, a Legionnaire from Highlands Post 69 in Avon Park, FL, was elected Department Commander on June 17, 2023, during the 104th Department Convention in Orlando, Florida. Commander Raymond is an eighteen-year continuous member, earning his eligibility through his honorable service in the U.S. Air Force from 1976-1985. A veteran of the Lebanon-Grenada era, Commander Raymond served as an Inflight Refueling Operator Technician.
Commander Raymond was born in Haverhill, Massachusetts, on November 16, 1955. He graduated from Haverhill High School in Haverhill, Massachusetts, in 1974. He furthered his education and attended Clinton Community College from 1982-1984, majoring in Business Management.
Commander Raymond is active in his local community. He has served on the Board of Directors of the Vietnam Wall of Southwest Florida since its inception in 2015. While Commander, Post 110 was the driving force and one of the leading fundraisers in constructing the prominent 50% Vietnam Wall Replica in Punta Gorda, Florida. He also served as Vice President of the Charlotte County Veterans Council for three terms. He served on the board of the Vietnam Education Foundation, which educates eighth-grade students on the history of the Vietnam War. Commander Raymond also served on the board of the highly successful “Welcome Home Vietnam Vets” music festival and is currently involved with fundraising for the future “William Gaines Memorial Park,” which honors the Marines who lost their lives in Beirut, Lebanon.
Commander Raymond has served in many post, district, area, and department positions for the last eighteen years. He served as Post 110 Commander for six years, from 2013-2019, 13th District Vice Commander from 2016-2017, 13th District Commander from 2017-2018, Southwest Area Commander from 2018-2019, Department 3rd Vice Commander from 2019-2021, Department 2nd Vice Commander from 2021-2022, and Department 1st Vice Commander from 2022-2023. Commander Raymond is also an active member of the Sons of The American Legion and the American Legion Riders.
Commander Raymond has been married to his wife Debra for the past 41 years, and together they have one son, Nicholas, and one daughter, Brandy, and six grandchildren. Mrs. Raymond is a Retired U.S. Air Force Master Sergeant and an active member of the Legion, Auxiliary, and Riders.
Commander Raymond’s primary goal as Department Commander is increasing membership through basic training. His mission statement is “Integrity, Loyalty, and Purpose”, and his slogan is “Proud to be Legion”. Commander Raymond’s fundraising project will be Florida Disaster Relief Fund and Children’s Organ Transplant Association (COTA). Florida Disaster Relief Fund is a program of The American Legion, Department of Florida, which provides aid to our Legion Family members in stricken areas in the event of local, state, or national disasters. COTA is a nonprofit organization that helps children and young adults who need a life-saving transplant by providing fundraising assistance and family support.
The American Legion, Department of Florida boasts over 106,000 veterans still serving their country and the State of Florida. With 1.5 million members at the National level, The American Legion is the Nation’s Largest Veterans’ Service Organization. The American Legion was founded in 1919 on the four pillars of National Security, Veterans Affairs, Americanism, and Youth Programs. For more information on how you can be involved with the American Legion or for an interview with Commander Raymond, please contact The American Legion, Department of Florida at 407-295-2631, ext. 239, or through email at commander@floridalegion.org.