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Legends in Alaska Aviation: Harold Esmailka

Brice Banning
Courtesy Brice Banning

Aviation plays an undeniable role in Alaska life; Alaska's aviators are the lifeline to more than 80 percent of the state's communities. With this in mind, the Legends in Alaska Aviation project celebrates the contributions long-time aviators have had on Alaska, while they are still around to celebrate with us.

Harold Esmailka

Harold and his wife Florence have been influential and inspirational leaders in aviation, in their church, and in their community for more than fifty years.  They have operated two major air carrier certificates and owned more than fifty aircraft, ranging from Piper Cubs up to DC-3’s, with a smattering of everything in between.  At one time they even owned helicopters.

In 1930, Harold’s Alaskan adventure began in a wood cutting camp on the south bank of the Yukon River about 11 miles above Kaltag. Soon after his birth in that remote camp, events changed Harold’s life.  When he was six months old, a micro-burst of wind hit his family’s camp, destroying almost everything they owned.  The only thing that survived was one fish net that had been set in the river.  His family realized they could not feed Harold, and his grandfather found a telegraph station, sending word to Nulato that an infant was in need of adoption.  When Peter and Martha Esmailka heard of the infant’s plight, they immediately decided to adopt the child.  They went to launch their boat to head down river to pick him up, but found they had no gas for the motor.  Peter sent Harold’s soon-to-be brother to the store to fetch five gallons of gas for the trip.  Harold recounts fondly that his brother never lets him forget the fact that he was worth only about five gallons of gas.

When Harold was twelve years old, his adoptive father passed away just before Harold started at Holy Cross Mission boarding school. This was his first exposure to formal education, as Harold had been raised in the traditional native lifestyle of hunting, fishing, trapping and gathering. 

At Holy Cross Harold met Brother George Feltes, an early Alaskan aviator who recognized Harold’s ability to be a fine mechanic. Brother Feltes was to become a major influence in his life. 

Harold recalls that the shop at Holy Cross was very rudimentary, with the most modern piece of equipment being a Model B Ford.  In 1951, Harold left Holy Cross to join the United States Army as a communication specialist in the infantry.  After basic training at Ft. Richardson, he was assigned to Ladd Field and earned the rank of Corporal. 

After separating from the Army, Harold went fishing! He and a couple Army buddies pooled their money and fished out of Wrangell, through Cross Sound and all the way up to Yakutat.  Harold told us it just wasn’t a good year to start a fishing business.  He returned to Fairbanks and worked at the F.E. Mining Company as a driller’s helper until he was laid off in November. 

Harold returned to Nulato to spend the trapping season gathering hides, and when the season was done, he came into Fairbanks to sell them.  After he had sold his hides, his brother told him about mechanic jobs at Eielson Air Force Base that required membership in the Operating Engineers Union Local 302.  He went to the union hall every day, until one day, his name was called.  When they asked him if he was a light duty or a heavy duty mechanic, Harold didn’t know the difference.  He thought about it, chose heavy duty, and “poof”:  he was a heavy duty mechanic!  He borrowed tools from his brother to start, began making “good money” and saved to purchase something he had wanted forever:  an airplane.

Harold bought a 65-horsepower Aeronca Chief in 1954 for $1,250He now had a good job, an airplane, and NO pilot’s license so he enrolled at Interior Airways on Fairbanks International Airport, quickly earning his license. 

There were times when some doubted Harold’s potential to become a legend in Alaskan aviation.  During a 1955 flight to Holy Cross to show his airplane to Brother Feltes, Harold was forced down by bad weather in Anvik. The fierce storm meant he couldn’t even turn his plane around. Dave Wilcox, a local minister, came down to help and gave Harold shelter from the storm. As Harold sat, he became more and more fidgety, so he told the minister he wanted to check on his plane.  He started his aircraft and took off in the storm.  Years later the minister was happy to see Harold alive and well with a big aircraft hangar in Galena.

Harold flew his Aeronca Chief for several years, until deteriorating snowy weather forced him to land in a near whiteout on the Tanana River.  It was so bad he used willow trees on the riverbank as a landing guide.  Harold spent the night in his aircraft and woke to waist-deep snow. As he struggled to free his plane, a U.S. Army rescue chopper found him and asked if he was okay. Harold asked them to help him push. That’s exactly what they did, and he flew away! Harold decided he needed more than the Aeronca’s narrow skis and 65-horsepower engine, so he flew to Fairbanks and bought a SuperCub.

On Christmas Day in 1958, Harold flew a priest from Koyukuk to Ruby and spent the night, waking to another heavy snowfall.  He needed to borrow a broom to sweep the snow off the plane’s wings.  As Harold tells the story, “I went into the store to borrow a broom, and I saw this boy and girl wrestling on floor.  I thought to myself, now there’s a good looking girl.”  When he found out why they were wrestling—Florence’s brother had given her some money and was trying to take it back—Harold thought, “Wow, she’s pretty and she likes to hold on to her money!”  That day a courtship started that led to a marriage that has lasted over 50 years. 

A life in Ruby, Alaska

Harold and Florence were married Nov. 5, 1960, in Nulato.  They settled in Ruby and, in 1964, bought the local store, calling it the “Ruby Trading Company.” It was called the trading post because until the late 60’s, a good portion of the transactions were conducted through barter, such as fish, furs and firewood in exchange for store goods. 

They lived in the store. Florence recalls that they finally got running water when a neighbor ran a water hose down to the store.  During this time, Harold was buying airplanes to establish Harold’s Air Service.  He wanted to buy another aircraft, and Florence, who was waiting for a house, told him, “The next plane you buy better be well insulated, because you’re going to be sleeping in it!”  Well, Harold didn’t have to sleep in the airplane, he continued to buy airplanes, and in 1970 Harold’s Air Service was formed. 

At its peak, Harold’s Air Service provided service to 63 villages and had 28 aircraft, including a turbine Douglas DC-3—the first one certified in the world.  Harold continually expanded the company, acquiring small Part 135 operators along the way.  When the base at Ruby became too small, Harold expanded into Galena where the other operators wouldn’t sell fuel to their new competitor. 

Harold recalls fondly the purchase of Aniak’s Vanderpool Flying Service, owned by Bob Vanderpool and operating from a 16x20 shack.  When Harold arrived the shack was packed with locals who had come to see the purchase.  After some talk, Harold and Bob stepped out into the rain and made the deal on a handshake. 

Harold’s Air Service soon provided medivac flights for the region.   Harold and Florence fondly recall 7 in-flight births, with one woman so impressed with their service that she delivered twice in their plane! 

A short retirement

Not only did Harold run a reliable organization, he ran a safe one.  But there were occasional mishaps. A friend and he were out hunting wolves, with Harold dragging the skis through snow to clear a landing spot.  Spruce cones became lodged in the intake.  Harold tried to land but caught a spruce tree in the skis and nosed the plane over.  They set to fixing the bent propeller and broken ski, Harold using a spruce tree on the ski and his partner scouting for two trees marked Hartzel and Propeller between which they could straighten their bent metal.  Harold said the plane flew “kind of funny” on the way back, but they made it.  When they landed they noticed a three-foot section of spruce tree had been caught in the skis.  Later, when Harold had the propeller inspected, the repair station couldn’t find a thing wrong with it!  It pays to use the right trees.

In 1982 it was time to retire and Harold and Florence sold Harold’s Air Service to Gannayo Native Corporation. Harold stayed on for a year to help with the transition.  During the time Harold was managing the air service the DC-3 was purchased.  

Retirement lasted 3 short years, until the 1986 purchase of Tanana Air Service and a Cherokee Six.  Within a few short years, Harold again built a small company into one that will forever be synonymous with Alaska aviation.  Harold based Tanana Air Service in Fairbanks and began hauling mail and providing charter service.  Tanana Air Service was highly successful, and again, an extremely safe operation, eventually consisting of a fleet of Lances, Cherokee Six’s and Navajo’s. This commuter airline provided cargo, mail, and passenger service to some eighty communities in Interior Alaska.  While Harold ran Tanana Air Service, they provided free transportation to the Fairbanks Catholic Diocese for their clergy and their Brothers and Sisters that served the local villages.  In 2004, Harold and Florence again retired, and sold the air service.  It is still a successful operation, ran out of McGrath now.  Throughout the years, Harold has owned more than 50 aircraft and several 135 certificates.  All have been wildly successful, efficient and safe operations, yet Harold remains quietly humble about the whole thing.  When asked the key to his many successes, he stated “The key to the whole thing was the people who worked for me. They were smart, loyal, and hard working.”