In late 1944, while serving in the Michigan National Guard, Benjamin started flying lessons in a single engine land plane and five and a half hours later, he soloed.
By spring of 1945, his interests turned to sea planes, which he flew on the Detroit River during that year.

The 1947 photo of Benjamin in an L-5 reconnaissance plane was taken at the Sendia Air Base in Japan where he served with the 11th Airborne as a part of the Asiatic Pacific Occupation Army.

His first license was from Michigan Aeronautics, which he still has to this day; and in 1946 the FAA issued his license for land and sea rating. By 1984, the Michigan Aeronautics Commission entered his name as part of Michigan Aviation history.

For 12 years, he pulled banners for various events part-time for his own company while working for R.L. Polk as a building engineer. During this time, he also was the co-pilot for their private Gulfstream I and King Air aircrafts.

Even though his health does not allow him to fly any longer, he remains a strong supporter of aviation in his local community.