The American flag has a special bond with our military. For Richard O. “Skip” Middleton II (Brigadier General, USAF retired), it represents “the rich history of our country and the sacrifices made by many for many more.”
General Skip Middleton was born in 1957, during the Cold War, a nearly five-decade-long state of political conflict, military tension, proxy wars and economic competition between the Soviet Union and the U.S. Fear of a nuclear attack was a constant threat.
According to General Skip Middleton, motivation to join the military was pretty simple: “Family history, plus an overall sense of service and responsibility to the nation. For me, service is to be part of something larger than yourself.” To better understand his professionalism and love of country, it helps to know more about his family’s tradition of honorable military service.
It is the winter of 1777-1778, and the American Revolution has been underway for more than two years. General George Washington’s American Continental Army of 12,000 soldiers camped in the cold and freezing temperatures at Valley Forge. During this time period, the largely volunteer militia trained and became a confident military force, effectively giving birth to the American army. Included among General Washington’s command staff was a Middleton ancestor with the rank of colonel, along with his four brothers who fought with the American militia against the British.
The Middleton family history of patriotic duty continued with the service of three relatives in the Civil War, specifically, General Skip Middleton’s great-great-grandfather, Captain Richard Middleton
, and two of his brothers, William and John Middleton. (Note: John Middleton enlisted at the age of 13 and achieved the rank of brigadier general by the time the war ended).
Captain Richard Middleton’s M Company, the 50th New York Engineers, participated in a number of Civil War historical engagements, including Harpers Ferry, Gettysburg and Fredericksburg. On April 9, 1865, Captain Richard Middleton’s company engaged in the Battle of Appomattox Courthouse, which concluded in General Lee’s surrender to end the Civil War. One year earlier, William Smith, the New York editor of the Owego Times, referenced Captain Richard Middleton in an April 1864 article, writing, “You can tell all of our friends at home that Captain Middleton is one of God’s best men, and knows his duty as a soldier and officer.”
Today, Captain Richard Middleton’s inscribed cavalry sword 
is prominently displayed in General Skip Middleton’s home, along with a section of tree containing several embedded rifle balls resulting from his ducking behind a tree to avoid shots taken at him during the battle at Fredericksburg.
The Middleton family military tradition continued in World War I, with General Skip Middleton’s grandfather’s service in France with the Army Medical Corps. Family service during World War II included General Skip Middleton’s father, Richard Arthur Middleton, and three of his uncles. One uncle became a fighter pilot ace, who was credited with downing six German planes in air-to-air combat, while another is buried in Arlington National Cemetery, after having retired as an army colonel.
This generational patriotic devotion and military service continued with General Skip Middleton. Following graduation from The Citadel, First Lieutenant Skip Middleton was soon assigned to a West German Luftwaffe base during the 1980s Cold War, where he was embedded into the 31st West German Fighter Bomber Wing. This 25-year-old young officer had significant responsibilities which included the potential arming of nuclear bombs as a counter-strike in the event of attack. To stay prepared for a required launch of nuclear armed aircraft sitting on alert, drills were continually run where messages had to be decoded and authenticated to access the safe with bomb arming codes. Codes were taken out to the awaiting aircraft and, ultimately, they simulated the arming of the bombs. Failure to complete all necessary actions within the required nine minutes resulted in loss of certification and possible reassignment of duties.
His next assignment, in 1988, took him to the Offutt Air Force Base in Omaha, Neb. Now 31 years old, Captain Skip Middleton was assigned to the battle staff for one of the Strategic Air Command (SAC) EC-135 specially configured Boeing 707 planes, which served as a command and control platform capable of deploying air, land and sea-based nuclear forces located around the world. As an airborne battle staff logistics controller, he was responsible for monitoring potential nuclear detonations worldwide, determining capabilities of resources and tracking conditions and availability of all airfields, aircraft, air crews, weapons and fuel. This included the development of recovery plans for all returning strike aircraft away from the expected areas of nuclear fallout. Captain Skip Middleton logged 203 missions and nearly 1,800 hours airborne. These missions, named “Operation Looking Glass,” required a minimum of one plane to be continually airborne, 24/7, for more than 29 years, while the others remained on a 15-minute ground alert status.
It was during this time that President Ronald Reagan famously challenged Soviet Premier Mikhail Gorbachev in a 1987 speech, saying, “Mr. Gorbachev, tear down this wall!” The Berlin Wall did indeed come down in 1989, but the U.S. military remained on alert due to concerns about how East Germany or Russia might react to the unfolding events.
His years as a part of Operation Looking Glass were particularly insightful. “Flying on the SAC Airborne Command Post during the final days of the Cold War made a big impact on me. To have been a part of what had been necessary to bring this period of nuclear uncertainty to an end is something I am honored to have had a role in for our country,” General Skip Middleton shares.
For the past 17 years, General Skip Middleton has made his home in Frisco with his wife and four children. During this time, he was twice deployed to the Middle East and participated in Afghanistan’s Operation Enduring Freedom in 2002 (were he was awarded a Bronze Star), with a return trip to Afghanistan in 2009. He commanded an expeditionary logistics group, and was responsible for maintaining proper levels of the necessary military resources and supplies like medical equipment, food, ammunition and vehicles. He adds, “Throughout my Air Force career, I worked with, commanded and was commanded by exceptionally good Americans. The interaction and sense of camaraderie found in the military far exceeds anything in the civilian world.”
Today, General Skip Middleton puts to service his University of Oklahoma master’s degree in economics as a wealth advisor with LPL Financial, a comprehensive financial services firm. Having retired from the military in January of 2015, with more than 34 years of service, he remains very active in the Frisco American Legion, the Frisco Veterans of Foreign Wars, the Frisco Rotary Club and Frisco’s Chamber of Commerce International Business Council.
General Skip Middleton and his ancestors have demonstrated a long tradition of patriotism, professionalism and sense of duty to our country. A tradition, he believes, inspired by a prevailing commitment and sense of responsibility to do what is required to keep our nation safe, even when the decision may be difficult or unpopular.
