Air Force introduced airman to emerging computer technologies

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As he prepared for graduation from Butler (Missouri) High School in 1987, Tom Winters Jr. began weighing his options for college, vocational training or entering the workforce.

With a deep interest in automobile restoration, he traveled to his father’s hometown in Colorado after graduating to learn the trade, not realizing it would be the first step of his journey to the U.S. Air Force and a lengthy career working with computers.

“There was a shop in my father’s hometown of Howard, Colorado, that did automotive restoration on vehicles from prior to 1948,” Winters said. “Since I was interested in doing that myself, I moved out there and did an apprenticeship with them for about two years.”

It was during his stay in Colorado that he met a woman named Karen, and the two became engaged. However, when making only $5 an hour in his apprenticeship, he decided to move back to Missouri in 1989 and work for his father’s aircraft repair company.

His fiancée soon joined him in Missouri, and they married in November 1989. Several months later, with a wife and stepdaughter to provide for, he began considering the possibility of joining the military.

“I enlisted in the Air Force in April 1990, when I was 21 years old and just shy of being married for six months,” he said. “My father had been in the Air Force years earlier, so that is part of the reason I chose that branch.”

His initial training was completed at Lackland Air Force Base in Texas, followed by several weeks of training in computer operations in Biloxi, Mississippi. Winters said the concept of computers was relatively new to him since the technology had not been available at his high school in the late 1980s.

His first duty station, he discovered during his training, would be at Decimomannu Air Base on the Italian island of Sardinia. The excitement of such a unique opportunity was diminished when he was informed it was considered a remote assignment, meaning his wife and daughter would have to remain in the states.

During the time it took for his security clearance to process for his new assignment, the Air Force changed the designation of the air base to that of an accompanied tour.

“I got to Italy around late July 1990 and had to secure housing, so it was about two months before my family could come over and join me,” he recalled. “After I got there, I was assigned to the 7555th Tactical Training Squadron — one of only two tactical training squadrons in the world.”

He continued, “It was an Italian air base but there were American, German and British military personnel stationed there. I worked inside a secure mobile van inside a building without any windows and helped coordinate training deployments, transferring and receiving messages for our compound using an old teletype computer.”

Although he was scheduled for a two-year deployment, the United States chose to leave the base in July 1991, after Winters had only been there for a year. He then worked with reassignment personnel and was given a transfer to Myrtle Beach Air Force Base in South Carolina.

In this new location, he was part of the 354th Communications Squadron and soon started performing database administration using a Unisys 2200 mainframe system. A segment of his responsibilities was to print checks for military retirees in the area and ensure the information on them was correct.

This air base closed, and in March of 1993, he was transferred to Buckley Air National Guard Base (now Buckley Air Force Base) in Aurora, Colorado. He soon transitioned to database management and eventually became a trainer for the Second Space Warning Squadron.

“I left active duty in September 1995 and went into a full-time Air National Guard position at Buckley,” Winters said. “I was a lead computer operator, but eventually got into network administration and then network management.”

The airman deployed for a few weeks to Ahmed Al-Jaber Air Base in Kuwait in late April 1999. During the deployment, he received an offer for a contract job.

For the next 23 years, he was employed as a federal contractor, starting as a network engineer, and fulfilling roles of increasing responsibility including that of a project lead and program manager. Winters and his family relocated to near California, Missouri, in April of 2016, and he began working remotely in his contracting job.

He made the decision to leave federal contracting in November 2021, having been a senior program manager for the last several years. Seeking a new career entirely different from that which he had been doing, Winters reflected upon a brief experience from years earlier.

“Back in high school, I worked for my former brother-in-law, who owned a sign business for 35 years,” he said. “This was back when he hand-painted the signs, and I helped him do some of the installs.”

Since his relocation to California, Winters has purchased the necessary equipment and now operates Kustum Signs, LLC. Additionally, he is active with the Veterans of Foreign Wars in California, serving as quartermaster for his post.

“The Air Force was the second-best thing to ever happen to me — the first was getting married to my wife,” he said. “I was very fortunate to have enlisted at a time when computers were really coming on and with each successive job I was given, I learned more about them and progressed to positions of greater responsibility.”

Winters added, “From signing on that dotted line as a new enlistee to becoming a senior program manager as a federal contractor, everything in my career seemed to evolve from having made that decision to be in the Air Force.”

Jeremy P. Ämick is the author of the military compilation “Show-Me Veterans.”

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