Fleet Industry Remembers Michael Flanagan
KERNERSVILLE, NC - After learning about the passing of Michael Flanagan over the Christmas holiday, Automotive Fleet contacted some of Flanagan’s industry colleagues and friends to share their memories of him.

Michael Flanagan.
KERNERSVILLE, NC - After learning about the passing of Michael Flanagan over the Christmas holiday, Automotive Fleet contacted some of Flanagan’s industry colleagues and friends to share their memories of him.
Michael Flanagan, a former fleet management and leasing executive and consultant, passed away Dec. 24, 2011, in Kernersville, N.C., after a long illness. He was 65.
Flanagan began his fleet career at the New York offices of CIT Service Leasing in 1968 following service with the U.S. Marine Corps from 1965 to 1967. At the New York office he handled purchasing and used-car sales. He was soon promoted to the company’s Chicago sales office in 1969.

Michael Flanagan.
Flanagan worked for Al Cavalli, VP client relations and director, at CIT (and past NAFA president) and made an impression on his superior.
“I remember Mike [Flanagan] well. He worked for me in used-car sales at CIT Service Leasing as a young man recently out of the Marines. He was a big fella and a hard worker,” Cavalli recalled. “From there, he was made our district sales manager in Chicago and the rest is history, having made a name for himself in the industry. I'm sure he'll be missed by his many friends.”
After CIT, Flanagan worked for Genway Fleet, Gambles C&M (which became D&K Financial), and then GE Capital Fleet Services as regional vice president. From 1991 until 1997, he then served as regional vice president for USFL & Associates Fleet. Flanagan then segued into fleet consulting with SGS, and then joined Atlantic/Millennium, a retail dealer and leasing company in Long Island, N.Y., before retiring in 2005.
After he retired, Flanagan began reflecting on his fleet career, writing to friends and colleagues about important touchstones, including his long-time readership of Automotive Fleet magazine, which he shared with Ed Bobit, Bobit Business Media chairman and founder of AF magazine.
“I got addicted to Automotive Fleet magazine and this part of your media empire is just a jewel and I’m never let down,” Flanagan wrote to Bobit in 2008. “I never shared this with you and I should have. The yearly Fact Book was carried on the road with me and I used it to do purchases and leasebacks. All fleet salespeople were to send into their home offices analysis leaseback information. It could take weeks to get these studies back. I learned from the first study done and your Fact Book how to do them myself. You had all the information per state license, title, and upfront tax, or over lease cost, etc. In the first three to four months with Gambles, I did three [analyses] and brought in close to 3,000 vehicles and 800 orders. Gambles was impressed. One of those studies was done in a Knights Inn in Cincinnati. We won the deal because of your magazine.”
For his part, Bobit recalled, “Mike knew our business and was welcomed by his clients and potential ones because of his open personality and knowledge he shared with everyone. He was able to distill the essentials into plain terms and he always had that personal friendliness with all of those in his path. In his way, he was a corporate warrior.”
Flanagan’s involvement with fleet extended beyond the office. He was involved in leading the industry through its professional organizations. He served as executive vice president and then president of the Automotive Fleet and Leasing Association (AFLA) in 1991 and 1992 respectively.
“Mike was a ‘car guy’ through and through,” recalled Bob Miesen, president of Gambles C&M (later D&K Financial Corp.) when Flanagan worked there. “I know that he was particularly proud of his affiliation with AFLA, its membership, and its charter. It gave him a full measure of professional and personal happiness and satisfaction.”
Flanagan was also a long-time member of NAFA, marking his 40th anniversary with the Association in 2008.
George Argueta, marketing manager for Corporate Claims Management, remembered Flanagan as a "beloved husband, father, grandfather, and ex-Marine. I know he is now with God and without pain. I will miss him and the memory of that Irish face."
Miesen recalled his colleague and good friend as “a good man with a big heart. In my years in the industry, I am not sure that I knew another person who loved being a part of it as much as Mike. For Mike, it was about God, family, friends, the fleet and leasing business, and importantly, Mike was unwavering in his loyalty and commitment to all those touchstones in his life. I will miss him.”
The son of Irish immigrants, Flanagan grew up in the Bronx with his three siblings and a total of 17 foster siblings (up to four at a time) that his parents raised between 1951 and 1968. Flanagan is survived by his wife, Kathryn, three children, and five grandchildren.
More Operations

Fleet Has a Talent Pipeline Problem. What Comes Next? | AF News Recap
Where will fleet’s next generation of leaders come from? This week, we’re looking at the industry’s talent pipeline, what certification can add to a fleet career, how to build an award-worthy track record, and the return of Automotive Fleet’s Personal Use Survey.
Read More →
Smith System Launches Driver Risk Management Program
Fleets have more driver data than ever, but identifying risky behavior doesn't necessarily correct it. Smith System's new Driver Risk Management program combines monitoring, training, and follow-up coaching to help fleets connect risk signals with driver intervention.
Read More →
Automotive Fleet Opens 2026 Personal Use Survey for Commercial Fleet Managers
Less than two weeks left! Commercial and corporate fleet managers are invited to share how their organizations handle company vehicle personal-use policies, charges, and driver eligibility.
Read More →
From AI Prompts to AI-Generated Safety Songs | AF News Recap
Can better prompts make AI more useful for fleet managers? This week, we’re breaking down smarter fleet analysis, an AI-assisted experiment that turned safety training into music, and what happened to fuel prices in August.
Read More →
How to Write Better AI Prompts for Fleet Analysis
Include these six elements in your fleet prompts to generate more relevant analysis and accurate answers.
Read More →
Fleet Meets: Eric Kilgore
This edition of the Fleet Meets series features one of the industry's best leaders driving multi-market and national operations.
Read More →
Why Reactive Fleet Management Is Becoming Too Expensive to Sustain
Research highlights a growing need for proactive management strategies to address rising costs in fleet operations effectively.
Read More →
What Your Fleet KPIs Aren’t Telling You
Tracking fleet metrics is only useful when the data leads to better decisions. This guide helps fleet leaders assess cost, utilization, and downtime more accurately, identify performance gaps, and prioritize the actions that can improve operational results.
Read More →
Hidden in Plain Sight: Fleet Compliance Risks
Fleet compliance isn't just about having policies — it's about consistently enforcing them. This practical guide reveals six hidden compliance risks common in public sector and shared fleet operations and outlines proven strategies to improve visibility, accountability, and audit readiness
Read More →
Turning Fleet Payment Data into Executive Insights
Does data alone drive results in operations?
Read More →