Robert Hollis ‘Bob’ Strauss Jr. was born in Monterey, CA, the first of three children to Robert Hollis ’35 and Elizabeth O’Malley Strauss. Bob’s father was an active duty U.S. Air Force division commander, his grandfather (USNA 1908) was an Army Air Corps pioneer, and his great uncle William D. Connor (USMA 1897) was the 36th Superintendent of USMA. Inspired by family history, Bob showed interest in attending West Point from an early age. Growing up as an Air Force fledgling, he moved every two years, from one school and base to the next, from Alabama to Newfoundland. He graduated from Jesuit High School in Tampa, FL, attended Columbian Prep School in Washington, DC, and entered the Academy in July 1957.

As a cadet, Bob met every academic challenge with style and every athletic opportunity with great skill. A 6'6" corps squad basketball player, he was the best jumper on the team, was able to dunk easily even before breakaway rims, and was the only one who could cover Princeton’s Bill Bradley in his prime. Bob also skillfully played water polo, dominating the field of play. Opponents recall Bob sending them to the bottom of the pool during intramural competition, and, to this day, some report drowning flashbacks when they see water. Additionally, at the culmination of his cadet playing days, he also participated in the formation of the West Point Rugby Team.

Companymates recount an episode during Bob’s yearling year when General Omar Bradley, Class of 1915, visited West Point and was invited to see his old room, a Company M-2 firstie room across the hall from Bob’s. In preparation for the general’s visit, all unnecessary and unauthorized items were moved to Bob’s room. When the general was shown the staged room, he indicated it wasn’t his: his was across the hall. The official party then walked in on Bob, who was dressed in casual attire and surrounded by non-TO&E equipment, small appliances, magazines, and laundry. To the relief of all involved, including the Commandant, the five-star defused the situation by saying, “Now this is how I remember it.”

Bob’s stature, charm, and generosity were notable, but all remember his wonderful sense of humor most vividly. Simply said, he made everything fun. He always made people laugh, and his quick retorts could raise morale or deflate the biggest ego with uncanny truth. His humor helped classmates handle stressful situations, and his ability to laugh at himself endeared him to others. Decades later, classmates and friends remember the lasting monikers he assigned, including ‘Squirrel,’ ‘Turtle,’ and ‘Light Bulb.’

Bob graduated in June 1961 and was commissioned in the U.S. Air Force. He attended pilot training at Webb Air Force Base (AFB), TX. As a member of flight school Class 63B, he won the respect of his classmates and led his squadron’s basketball team to the base and ATC championships. His father, Brigadier General Robert Hollis Strauss, gave the graduation-dinner keynote address, and upon the award of his wings Bob Jr. became one of the first third-generation pilots in U.S. military history.

In 1962, Bob reported to Connelly AFB, TX and soon after married and had two sons. He was assigned to fly student navigators in a twin engine T-29 but quickly volunteered to support early U.S. military contingency operations in Vietnam. At the time, there was only one TDY slot available, so he cut cards with his classmate to see who would deploy. Bob drew a 10 to his classmate’s 8. One of the highlights of that assignment was his initial training in Singapore at the Royal Air Force Survival Training School. In Vietnam, Bob flew 150 C-123 combat support missions at a time when the Army and Air Force were in the process of developing capabilities and responsibilities for aerial resupply and ground support operations.

In 1966, Bob resigned from the Air Force to join Continental Airlines. He began as a co-pilot on military contract flights from Los Angeles to Southeast Asia and advanced quickly to become a captain in four years. In addition to flying, he served as Continental Airlines’ representative to the U.S. Airline Pilots Association, the largest pilots’ union at that time, and he was elected to serve on the association’s executive board. Bob was held in high regard for his ability to articulate pilot demands while also understanding management challenges. His efforts were credited with improving labor-management relations throughout the airline industry. His commanding presence along with an ability to think quickly, assess, articulate, and use humor to best advantage served him well. In 1978, due to illness, he relinquished flight status but continued to represent Continental pilots in a role that brought him added respect and demonstrated to both his fellow pilots and the industry that he was destined for greater challenges and responsibility.

Much too soon, Bob succumbed to cancer in March 1981. He is buried with family members in the West Point Cemetery. His niece Caroline Leigh Kosco, who graduated in 2006, took her commissioning oath as an Army second lieutenant at the family gravesite with family, friends, and faculty attending. Bob would be proud to know the West Point family tradition continues.

Aloft in solitude of space,
Uphold them with Thy saving grace
O God, protect the men who fly
Thru lonely ways beneath the sky.
— The Air Force Hymn, 4th Stanza

— Family, Friends, and Classmates