Jonathan Stickley Shafer

CAPTAIN JONATHAN STICKLEY SHAFER
U.S. Air Force Academy Class of 1959
Years of Service: 10

Jonathan "Jon" Stickley Shafer was raised in Lake Forest, Illinois. Receiving a Congressional appointment to the newly established United States Air Force Academy, he entered in the summer of 1955 as a member of the Academy’s historic inaugural Class of 1959.

Assigned to Cadet Squadron 10, Jon distinguished himself early as a cadet who was exceptionally mature, reliable, relatable, and having of sound judgment. He was an accomplished athlete on the USAFA Gymnastics Team, where he specialized in the parallel bars competition.

Beyond athletics, Jon brought strong artistic talents to the Cadet Wing. Passionate about art and design, he frequently created artistic works during his off-duty time and contributed to the artistic design of the Class of 1959 class ring—helping establish a visual tradition for all future Academy classes.

MILITARY SERVICE & FLYING CAREER

Upon graduating on June 3, 1959, Jon was commissioned as an officer in the United States Air Force and entered undergraduate pilot training. He successfully earned his command pilot wings and flew jet aircraft during his decade of active service.

Among his key duty assignments, Jon served as an Instructor Pilot (IP) with the 3575th Pilot Training Squadron at Vance Air Force Base, Oklahoma. Over 10 years of military service, Captain Shafer mentored and trained dozens of student aviators, passing on the precision airmanship and leadership principles forged at the Academy before transitioning to civilian executive life.

BUSINESS CAREER & CIVILIAN LEADERSHIP

Following his military service, Jon translated his organizational leadership and financial acumen into a successful executive career spanning over three decades in corporate management, investment, and finance:

• Container Corporation of America (Carol Stream, IL): Sales Manager (1983–1984)
• Procorp Inc. (Framingham, MA): Vice President (1984–1992)
• Shafer Enterprises Inc. (Southport, CT): Chief Executive Officer (1992–1998)
• Defined Risk Management Co.: Managing Director (1998–2006)
• Connecticut Investment Management Inc. (Palm Beach, FL): Senior Vice President (2006–2009)
• AD Communications, Inc. (Westport, CT): Chief Financial Officer (2009)

PERSONAL LIFE, FAMILY & LEGACY

Jon was married for 54 years to his beloved wife, Margot Van Gilder Shafer. Together they raised three children: Jonathan Stickley Shafer Jr., Peter Dell Shafer, and Sheridan Lee Shafer. Jon was also a devoted grandfather to eight grandchildren: Jonathan III, Mary Lee, Faith, Joshua, Peter Jr., Isabella, Beatrix, and Willem.

In his community and spiritual life, Jon was an active parishioner at The Episcopal Church of Bethesda-by-the-Sea in Palm Beach, Florida.

Jonathan S. Shafer passed away in 2012, in West Palm Beach, Florida, following a brief illness. He is remembered by his USAFA '59 classmates, family, and fellow airmen as a dedicated officer, skilled aviator, and artistic visionary of the first graduating class and a loving, steady friend and family man.


EDUCATION


U.S. Air Force Academy Bachelor of Science (Class of 1959) 1955–1959
U.S. Air Force Pilot Training Jet Pilot Qualification / Wings 1959–1960

MEDALS & AWARDS


Air Force Command Pilot Wings Awarded upon completion of USAF Pilot Training
National Defense Service Medal Awarded for active military service
Air Force Longevity Service Ribbon Awarded for honorable military service

SERVICE ASSIGNMENTS


1955–1959 Cadet (CS-10) U.S. Air Force Academy (Lowry AFB / USAFA, CO)
1959–1960 Student Pilot USAF Undergraduate Pilot Training
1965–1970 Instructor Pilot 3575th Pilot Training Sq, Vance AFB, OK
1983–1984 Sales Manager Container Corp. of America, Carol Stream, IL
1984–1992 Vice President Procorp Inc., Framingham, MA
1992–1998 Chief Executive Officer Shafer Enterprises Inc., Southport, CT
1998–2006 Managing Director Defined Risk Management Co.
2006–2009 Senior Vice President Connecticut Investment Management Inc., Palm Beach, FL
2009 Chief Financial Officer AD Communications, Inc., Westport, CT