‘Rockstar’ Chief Warrant Officer Retires After Successful 25 Years of Service in the Illinois Army National Guard

The year was 2000. The original I-Pod was introduced. Dial up internet was all the rage. The average price for a gallon of gas was $1.52, MySpace didn't exist yet, and Chief Warrant Officer 3 Jennifer Rosa enlisted in the Illinois Army National Guard.

Rosa's 25 years of military service was celebrated with family, friends, and fellow service members at a retirement ceremony at the 33rd Infantry Brigade Combat Team's headquarters in Urbana, June 5.

"Twenty-five years in any career doesn't happen by mistake," said Maj. William Troccoli, the 33rd IBCT's administrative officer. "Today is a special day and arguably one of the most important events in any Soldier's career - retirement."

Rosa enlisted in the Illinois Army National Guard in December 2000 as an intelligence analyst and later reclassified as a Human Resources Soldier. She has served in many capacities throughout her career, including her final position as the 33rd's Human Resources technician, a position she's held since 2018.

"She has truly come up through the ranks as a Soldier," Troccoli said. "She enlisted as a Private First Class, rising to the rank of Master Sergeant before receiving an appointment as a Warrant Officer in 2019. She is ending her successful career as a Chief Warrant Officer 3 in the largest brigade in the Illinois Army National Guard."

Troccoli said Rosa has been the muscle behind five large brigade mobilizations to the Middle East as well as numerous overseas training missions and state activations.

In 2026, Rosa received the Colonel Robert L. Manning award from the Adjutant General Corps' Regimental Association for her contributions and influence on the Corps' mission. Manning was the 29th Chief of the Adjutant General's Corps, Commandant of the Adjutant General School, Chief of Army Bands, and President of the Adjutant General's Corps Regimental Association. The AGCRA Achievement Medal was renamed after Manning in 2013 to recognize his significant contributions to the Association.

"The award was well deserved," Troccoli said.

He thanked Rosa's family, including her husband, Leosvaldo, daughter, Alana, and sons, Paolo and Sebastian, for allowing the Illinois Army National Guard to borrow Rosa for the past 25 years.

"To her parents, Sandra and David, Chief is a rockstar," he said. "I am sure you are very proud of her accomplishments."

Lt. Col. Russell Hayes, the 33rd's officer in charge and executive officer, also thanked Rosa's family.

"The military asks a great deal of our servicemembers, but it demands as much from our families," Hayes said. "From deployments, long training missions, and late-night telephone calls, our families keep the homefront secure. Thank you for your unwavering support and congratulations on having Jennifer back."

Hayes said Rosa has had a successful career.

"The Illinois Army National Guard has 9,950 Soldiers with about 10 percent of that serving in the Active Guard and Reserve Program," Hayes said. "Of those 49 rise to the rank of Master Sergeant. And only 22 Warrant Officers serve in the AGR program."

Hayes said Rosa is one of the best warrant officers he has worked with during his career.

"She embodies everything a Warrant officer is, a subject matter expert and a professional," he said. "It is safe to say she has had a positive impact on thousands of Soldiers during her 25 years of service."

Hayes thanked Rosa for her service.

"As you hang up the uniform and begin this next chapter of your life, know the impact you have had on Soldiers will be felt long after you walk out the door," he said.

Troccoli said Rosa's retirement on the eve of the 82nd anniversary of D-Day wasn't by happenstance.

"This painting of the beach landings behind me here on the wall perfectly represents what the D-Day experience must have felt like for those Soldiers - the unknown, the fear, and above all else, the determination to accomplish the mission," he said. "Chief as you approach the eve of your own unknown and fearful journey into retirement, I have no doubt you will do wonderful things as you step into your next chapter."

Rosa said the ceremony wasn't only a celebration of her military career, but it signifies the closing of one chapter and the beginning of another.

"The first chapter began before I was born," Rosa said, noting her mother, Sandra Rivera served in the Illinois National Guard before transitioning to the U.S. Air Force active component in the early 1980s. "My father was active-duty Air Force before transitioning to the New York National Guard where he retired after more than 20 years of active service."

Rosa noted the proximity of the Northwest Armory in Chicago and her participation in the Army JROTC in High School was probably part of the reason she enlisted in the Army.

"Even after attending JROTC camp in 1999 at Fort McCoy, Wisconsin, I still enlisted in the Army," she said.

She said despite Troccoli's glowing review, her military career wasn't perfect.

"I won't say it was marred by imperfections, but marked by humanity," she said. "There may have been some personal obstacles that diverted attention but that's just how it goes sometimes."

Rosa pointed out that less than one percent of the U.S. population is actively serving in any component of the military.

"Of that one percent, less than 20 percent are women and less than 10 percent of women make it to retirement," she said. "Based on those statistics, two one hundredths of a percent of the general population are women military retirees. I've been fortunate to know some of those women and now I'm honored to join them."

Rosa said 25 years in any one organization is a long time.

"I don't have the rest of my life figured out yet, but I know there is a rest of my life," she said. "I want the rest of my life to start as soon as possible."

Rosa said people see one Soldier retire, but they don't see the family who served alongside that Soldier. Rosa took the time to thank her family for their support.

"To my husband, my true north, thank you for every sacrifice, every adjustment, every time you carried the load so I could do my job. I love you," she said. "To my children, I give you a compass as a reminder that while my military journey is ending, your journey is just beginning. Wherever life takes you, lead with courage and integrity."