Phil Bales as chief pilot for Northwestern Mutual life insurance company with their Dassault Falcon 10.
Published in Midwest Flyer Magazine August/September 2022 Digital Issue
When Phil Bales retired as chief pilot for Northwestern Mutual life insurance company, his contribution to the aviation community in Wisconsin was just beginning. Phil and his wife, Wanda, herself having soloed, raised six sons and four daughters, nearly all of whom contributed in some way to aviation. Most were pilots and aircraft owners, and in some cases, owners of aviation-related businesses. This is how it all started.
Phil and Wanda Bales with their 10 children, most of whom chose careers in aviation.
When Phil was 17 years old, he broke his leg in a skiing accident. Largely immobilized, he began hanging out at the Waukegan, Illinois airport (KUGN) while he healed. Soon he was a student pilot and eventually became proficient enough to be hired by the Army Air Corps which needed pilots during World War II.
After Phil and Wanda got married, they moved to Pine Bluff, Arkansas, where Phil was a flight instructor. This led to Phil being hired by Pan American-Grace Airways, better known as “Panagra,” which sent him to Lima, Peru, to fly DC-3s throughout South America. Seeking a more local flying job, he returned to his hometown of Zion, Illinois. Eventually, Phil was hired by Trostel Tannery in Milwaukee as a corporate pilot, which led to his career flying for Northwestern Mutual.
Phil didn’t particularly encourage his kids to fly, but they all seemed to naturally gravitate in that direction when he would occasionally take them on trips.
For 21 years straight, at least one of the 10 Bales kids walked the halls of Bay View High School.
Oldest son, Dwight, was the first to leave the nest and become a pilot for United Airlines. He began taking flying lessons in high school and was offered a job even before he earned his Commercial Pilot Certificate.
Second son, Jon, graduated from the University of Wisconsin-Milwaukee, then earned his Navy wings. He was first assigned as a basic jet flight instructor, then later became carrier qualified flying the Grumman A-6 Intruder, an all-weather, low-level nuclear attack jet aircraft.
Jon went into real estate, investing in several apartment buildings. He says his happiest days were working on the bench at Mitchell Aircraft Instruments, fixing artificial horizons and directional gyros.
Oldest daughter, Bonnie, was a flight attendant for United. That was back in the day when being a “stewardess” was a glamorous job.
Third and fourth sons, Jeff, and Peter, became Army pilots during the Vietnam War. Jeff flew fixed-wing aircraft, and Peter, helicopters. The Bales brothers managed to survive being shot down and crash landings.
Second daughter, Katie, earned her Commercial Pilot Certificate and became an instructor of aircraft systems for United in Denver.
Third daughter, Maggie, worked as a ticket and gate agent for Eastern Airlines at General Mitchell International Airport in Milwaukee until that airline dissolved.
Tracy, the only one who didn’t work in aviation, got her license to drive semi-tractor trailers.
Fifth son, Chris, is currently a senior pilot with United. Jeff taught Chris to fly, and Chris built hours flying the WTMJ radio traffic watch and delivering checks for the U.S. Federal Reserve flying Beechcraft King Airs.
Finally, baby brother, Andy, along with his wife, Sondra, pursued flight attendant careers.
Several aviation-related businesses grew out of the family’s love of flying.
Phil and several of his sons purchased Mitchell Aircraft Instruments in 1975, a repair facility housed in the old Wisconsin Air National Guard building at General Mitchell International Airport on Howell Avenue in Milwaukee. Jeff was instrumental in founding the trade organization “Aircraft Instrument Association,” and also started an aircraft charter business. Peter used his knowledge of helicopters and now owns Tradewind International, a helicopter parts company in Janesville, Wisconsin.
(L/R) United Airlines pilots, brothers Chris Bales, Jeff Bales and Dwight Bales.
Altogether, seven of Phil and Wanda’s 10 children hold at least a Commercial Pilot Certificate.
The legacy has become a dynasty!
Now generations three and four are exploding on the scene. Whereas the 10 siblings were primarily based in Milwaukee, their kids and grandchildren are scattered around the country.
Dwight’s grandsons, Sam and Jack, are pilots. Sam is currently in training to fly for U.S. Customs and Border Protection. Jack flew drones for the military and is now an aircraft mechanic.
Jon’s son-in-law, Tim Bobinski, retired from the U.S. Air Force as an F-15 pilot, and now flys for United Parcel Service.
Jeff’s daughter, Natalie Boudreau, is training to become a flight attendant with United Airlines. Incidentally, Natalie has a Private Pilot Certificate.
Jeff Bales with his grandson, Jeffrey Boudreau, in the family’s Cessna 150. The aircraft is currently owned by Chris Bales and his daughter, Ally.
Jeff’s grandson, Jeffrey Boudreau, learned to fly before joining the Air Force. He is now in the pilot program at the University of North Dakota in Grand Forks.
Peter’s grandsons, Michael and Nicholas Prindiville, are in the Air Force. Michael is a loadmaster on a Lockheed C-130, and Nicholas is a computer specialist with a search and rescue unit, currently serving in Japan.
Maggie’s son, Garrett Hennig, is a private pilot and an aerospace engineer working on electric flight aircraft and drones.
Chris Bales’ daughter, Ally, is a new hire at United Airlines, flying the Boeing 787. She is seen here with her dad at her “wing pinning” ceremony in June 2022. As a senior pilot with United, Chris hopes to fly a trip with her before he retires next May.
Andy and his son, Evan, worked briefly together as mechanics for “SpaceX” in Cape Canaveral, Florida. Andy’s other son, AJ, worked as a mechanic with “Starfighters” at NASA’s Kennedy Space Center. Starfighters operates the only fleet of flight-ready, supersonic Lockheed F-104 Starfighter aircraft in the world and feature the aircraft in a civilian demonstration team. The Starfighters aircraft are available for a variety of government and commercial missions. The boys then changed jobs to work for “Blue Origin,” then AJ went back to work at Starfighters.
Chris’ daughter, Ally, is a new hire at United, flying the 787. Chris hopes to fly a trip with her before he retires next May.
It’s amazing that a high school student’s broken leg could lead that student to learning how to fly and starting an aviation family legacy!
