Women's History Month: OSI’s first female deputy CC shares story

  • Published
  • By Thomas Brading
  • OSI Public Affairs

Marking a full-circle journey, retired Col. Karen A. Esaias, who made history as OSI’s first female deputy commander in 2005, returned as the guest speaker at the second annual OSI Women’s History Month luncheon March 28, 2024, an event celebrating the contributions of women within the Office of Special Investigations. 

Esaias's path to leadership started at OSI Det. 711, Tyndall Air Force Base, Florida, between 1983 and 1985, she served initially as an operations officer then commander. It was a time, she said, women were significantly underrepresented. 

When Esaias came into the Air Force, it comprised only 7% women, she said, but it was never about making history, it was about being the hardest worker she could. 

"I think they recognized my talent and intellect and hard work," she said. 

This commitment to hard work propelled her into new roles at OSI, like as chief of antiterrorism at OSI District 68 at Torrejon Air Base, Spain, targeting threats in Greece in the late 1980s, and later leading antiterrorism and criminal investigations at OSI headquarters in Bolling Air Force Base, D.C.

Esaias's journey also led her to the U.S. Army School of the Americas at Fort Benning, Georgia, an experience different than the typical Air Force Professional Military Education and ultimately led to her meeting her future husband. 

Her assignments extended beyond traditional OSI roles, too, which included a two-year stint in Quarry Heights, Panama, first as a treaty officer and executive at U.S. Southern Command. “While at SOUTHCOM, I missed OSI desperately,” she said. “I used to swing by the local detachment and say, ‘can you tell me anything?’ One of the things that I think ties most OSI agents together is we're inquisitive by nature.”

Following her return to OSI as Det. 302 commander at Andrews Air Force Base, Maryland, Esaias faced a pivotal moment when Brig. Gen. Francis X. Taylor, then OSI commander, who offered her the opportunity to establish the Washington Field Office, a role that would cement her legacy as OSI's first female squadron commander. 

Esaias went on to lead another squadron, this time overseas at OSI 53rd Field Investigations Squadron at Aviano Air Base, Italy, where she started working alongside ret. Brig. Gen. Dana Simmons, OSI’s commander from 2005-2010. 

It was Simmons, years later, who met with Esaias while she was 8th Field Investigations Region commander at Peterson Air Force Base, Colorado. In 2005, Simmons was named OSI’s commander, and according to him, there was only one choice for deputy commander. 

“She was my only pick to be [deputy] commander,” Simmons said. “She was it, because I knew her capability and I knew how strong and dedicated she was, but more importantly, I knew that she could spot talent and she knew how to build and challenge talent.”

She accepted the role, and the rest is history.

“It didn't feel like a big deal because it felt natural since I had gone through the career that I had in OSI,” Esaias said. “It felt like a natural fit.”

“She was the first woman [deputy] commander, but we never made it a spectacle, or we never made it a key point of decision process,” Simmons said. “I had 32 colonels at the time, and she was probably number one or two in every category that I could count them in.”

In the years that followed, Esaias retired from OSI and moved back to Pennsylvania, where she lives today.

Her return to the spotlight as guest speaker, both a nod to her pioneering role and a testament to her enduring influence, set the stage for Esaias to share her story, as well as the ongoing progress within OSI.