Married fighter pilots with Sterling ties soar the skies side by side over Japan

STERLING – For Air Force Capts. Tanner “Brüt” Massey and Sydney “Menace” Shephard, the view from 30,000 feet is not only a mission – it’s a shared way of life.

The married fighter pilots, both currently stationed in northern Japan, fly F-16 training missions together, serving their country while navigating military life side by side in the air and at home.

Massey, a 2015 Sterling High School graduate, and Shephard have been in the Air Force for about five years. They met as cadets in the Air Force ROTC program at the University of Illinois Urbana-Champaign, where what started as a college friendship eventually turned into a lifelong partnership.

“It definitely wasn’t love at first sight – at least not for her,” Massey recalled. “I had to work harder to get her attention than anything else I’d ever done.”

Shephard jokingly agrees, saying their relationship started when “a boy invited himself to a girl’s family Christmas and then never left.”

The couple married in March 2020, just before Shephard’s graduation and their move to their first duty station for pilot training. Despite the start of the COVID-19 pandemic, they launched into a demanding but rewarding military journey, one that has taken them across the globe – from training in the U.S. to deployments in South Korea and now Japan.

Known as the “Mighty Viper,” flying F-16s is a dream the two share.

“It’s a welcome challenge,” Shephard said. “It’s like flying down a backroad listening to ‘Thunderstruck.’”

Massey echoed her sentiment, calling the aircraft a “phenomenal” multirole fighter that remains one of the most lethal platforms despite being fourth generation.

The pair flies missions in the same formation, something few military couples get to experience.

“It’s a cool and unique experience to get to fly alongside your spouse,” Shephard said. “You get a front-row seat to their growth as a pilot, which is awesome, and you also get to see all of their funny little mistakes to tease them about later.”

Although they fly in separate jets, their bond translates into an intuitive partnership in the skies.

“The real advantage with Sydney is more personal – it’s the ability to read subtle cues, like a slight change in her tone over the radio,” Massey said. “Usually, it’s when I’m pushing her patience a little too far.”

However, both Shephard and Massey emphasized that all fighter pilots they serve with are highly trained and capable, and personal familiarity is only one part of a larger team effort.

The couple has flown “too many training missions together to count,” said Shephard, with Massey logging almost 470 flying hours to date.

The pair has been stationed in Japan since late 2024 and is currently immersed in frequent flight training and preparing for pilot upgrades. Off duty, they have been settling into their home and enjoying winter sports and travel.

“We’re diving into the local culture,” Massey said.

Future travel plans include destinations such as Bali, Vietnam and New Zealand.

Their future in the Air Force remains open-ended. Both have about six years left in their initial 10-year pilot commitments and are considering continuing active duty or transitioning to the Air National Guard.

“We will stay in the military as long as it still fits our lifestyle and family goals,” Shephard said.

For now, the pair continues to dominate the skies together.