Harry Sargeant III

Sargeant also appears to have been the major contributor supporting Giuliani's efforts to pressure the Ukraine to influence the 2020 election efforts of President Trump.

In the 2008 presidential race Sargeant donated to onetime Republican front-runner Rudolph W. Giuliani, Mitt Romney, and eventual Republican nominee Senator John McCain. Crist had been considered as a possible McCain running mate in 2008 before running as an Independent candidate for the United States Senate from Florida in 2010.

A major military defense contractor, in 2004 Sargeant's International Oil Trading Company (IOTC), a start-up under his guide, won an initial Pentagon contract to supply petroleum to U.S. troops and coalition forces in Iraq after the original contractor failed to perform. Over the course of the next five years IOTC quickly grew to accumulate more than $2.66 billion awards from the Pentagon to deliver fuel to troops in Iraq. Because of the increasing number of ambushes on fuel convoys running the southern corridor from Kuwait to Baghdad, the Department of Defense required that all fuel and oil supplies bound for northern bases had to transit Jordan and enter Iraq through Al Anbar Province, Ramadi, and on to Baghdad. Through diplomatic skill, a critical letter of authorization was obtained by Sargeant from Jordanian authorities allowing IOTC to transit the country. Subsequent DoD contracts escalated in value year over year as demand for oil and fuels increased for Central Command forces, particularly during the months of the surge of U.S. Forces into Iraq.

In 1992 Sargeant began acquiring asphalt tankers in earnest, and within four years he had grown the young company to a fleet of six asphalt tankers, one ocean tug, three ocean barges and several hundred bulk containers. He also purchased and converted the vessel Asphalt Commander, which at the time was the largest asphalt tanker in the world at 35,000 dead-weight tons. Sargeant continued acquisition of large tankers throughout the remainder of the 1990s and into the next millennium, accumulating a dozen ships by the time of the Iraq War. In a tip of the hat to his alma mater FSU, Sargeant would go on to name one large tanker, a 108.5 meter ship, the Asphalt Seminole.

A longtime major Republican fundraiser and active behind the scenes in Florida politics since the mid-1990s, Sargeant has had a long-standing close relationship with former governor of Florida Charlie Crist, both being Pi Kappa Alpha, (πΚΑ) fraternity brothers in the 1970s at Florida State University. Following Crist's gubernatorial victory, Crist tapped Sargeant as the state Republican Party's Finance Chairman, a non-paying post he held until early 2009. He resigned the post shortly before a Sargeant Marine employee, sales coordinator Ala'a al-Ali, was indicted for illegal donations to the campaigns of Charlie Crist and John McCain.

Upon leaving Marine Corps active duty in 1987, Sargeant joined Delta Air Lines as a line pilot, however soon left Delta to take the helm at Sargeant Marine Inc. a small shipping company his father, Harry Sargeant Sr., himself a retired Naval Officer, had founded in 1983. Initially Sargeant focused on the transportation of asphalt products through chartered vessels. In 1989 Sargeant introduced innovations into the international market, such as ISO bitumen containers, that would enable the shipment of his asphalt products to remote destinations worldwide.

Graduating from Florida State University in 1979 with a Bachelor of Science in Business, Sargeant entered the Marine Corps attending Basic School after commissioning as a Second Lieutenant, followed by Naval flight school, where he earned his pilot wings in 1981 from Kingsville, Texas. Sargeant then joined the Black Sheep, Marine Attack Squadron 214 (VMA-214). A fighter squadron steeped in rich history and lore, the Black Sheep was the same squadron made famous in World War II, and commanded by Colonel Gregory "Pappy" Boyington. As a fighter pilot, Sargeant's mission in the A-4M Skyhawk was to provide offensive air support, armed reconnaissance, and air-defense for Marine expeditionary forces, and he continued to serve in the Marine Corps Reserves as a pilot, graduating from Navy Fighter Weapons School (Top Gun), and attaining the rank of Major before becoming inactive after 11 years of continual active duty and reserve service.

Harry Sargeant III (born December 30, 1957) is a billionaire diversified energy and shipping magnate from Florida. A former officer and fighter pilot in the United States Marine Corps, Sargeant operates an expansive, multibillion-dollar conglomerate of private global enterprises consisting of aviation companies, oil refineries, oil trading operations, alternative fuels development, and oil and asphalt shipping, his father's company, Sargeant Trading, being the largest fleet of asphalt tankers and barges in the world. He is also the owner of International Oil Trading Company (IOTC), a company that supplies aviation fuel to the U.S. Military in Iraq, and grosses billions of dollars annually. Sargeant is currently under investigation for communicating with Lev Parnas as a proxy for Rudy Giuliani during the Trump–Ukraine scandal and the Impeachment of Donald Trump.