May was born in Carberry, Manitoba, son of a carriage maker. His family moved to Edmonton in 1903, and while on the way they stayed with family and friends, and his two-year-old cousin gave him his nickname "Wop".
On April 9 Lieutenant May was transferred to No. 209 Squadron of what had just become the Royal Air Force (the squadron being a unit of the Royal Naval Air Service until April 1, when the RAF was created). The squadron was commanded by another Canadian, former school friend Roy Brown, who held an enviable record as a commander, having never lost a pilot under his command. May spent most of April getting used to his Sopwith Camel, but on the 20th was in combat with a German Fokker Triplane who crashed of his own accord during their brief fight.
The next day 209 Squadron was again on patrol with similar instructions as before – May was to stay out of the fights and simply keep an eye out. Around 10 a.m. the squadron encountered a group of Triplanes and attacked them, while May flew above the flight and circled. He spotted another plane doing the same thing and decided to attack, chasing this aircraft right into the middle of the fight. Spraying rounds in all directions, his guns soon jammed and he dove out of combat. Unknown to anyone at the time, May's target was Wolfram von Richthofen, cousin of Manfred von Richthofen, the Red Baron. Like May, Wolfram was also new to flying, and had also been told to simply sit it out above the fight and watch.
Manfred, seeing his cousin in trouble, watched May dive out of the fight and started to chase him. This was his preferred method of attack, looking for aircraft in trouble and attacking them. However, he was also careful to never chase aircraft over enemy lines, something he had avoided in years of combat. Watching von Richthofen chasing May, Roy Brown noticed the chase from above and dove his damaged aircraft down intercepting the action just west of the Church, and firing at the red Triplane. As May noted in his combat report: "21/4/18 Camel D3326 90 minutes Engaged 15 to 20 triplanes - claimed one. Blue one. Several on my tail, came out with red triplane on my tail which followed me down to the ground and over the line on my tail all the time got several bursts into me but didn’t hit me. When we got across the lines he was shot down by Capt. Brown. I saw him crash into side of hill. Came back with Capt. We afterward found out that the triplane (red) was the famous German airman Baron Richthofen. He was killed."
May continued flying with 209 Squadron until the end of the war, and eventually claimed 1 and 1 shared aircraft captured, 6 and 1 shared destroyed, and 3 and 1 shared 'out of control'. He was awarded the Distinguished Flying Cross in 1918. He relinquished his RAF commission on 8 May 1919 in the rank of Captain.
In 1924 the business failed, and May married Violet "Vi" Bode in November. He decided to get a "real" job, joining National Cash Register in Dayton, Ohio where he went for training. While working on a lathe he was hit in the eye by a shard of steel, and from then until 1938 he was slowly going blind. Convinced that flying really was his calling, he formed the Edmonton and North Alberta Flying Club in 1927, and became a flight instructor.
In December 1928 Bert Logan, an employee of the Hudson's Bay Company was posted to Little Red River, Alberta, on arrival he was unpacking when he suddenly got very ill. His wife, a nurse, realized he had diphtheria, and a desperate effort started to get inoculations to the town before anyone else was seriously infected. Simply getting the word out that help was needed was an adventure in its own, at the time there were no roads in the north, and the nearest telegraph station was miles away over a frozen landscape. The message eventually reached Edmonton, and on January 1 May was asked if he could deliver the medicine. He left with another flying club member, Vic Horner, the next day around noon, and landed on a lake for the night just before 4 p.m. when it was becoming dark. They refueled on the Peace River and continued their flight, arriving in Fort Vermilion at 3 p.m. A group had just arrived from Little Red River and the drugs were quickly distributed. They had to stop in Peace River on the return flight due to engine damage from the low quality fuels, and didn't arrive back in Edmonton until the 7th. By this point his flight had become known across Canada as "the race against death", and he and the mayor arrived to find a media circus waiting for them in town.
The news of this remarkable flight helped May establish a new company, Commerial Airways, to provide air service to Northern Canada. The Company won a government contract for air mail to the Northwest Territories. A service that had been pioneered by Punch Dickins rival Western Canada Airways. Both companies would eventually become part of Canadian Pacific Air Lines.
In early 1932 May was involved in another manhunt, this time for Albert Johnson, soon known as the Mad Trapper. While serving a search warrant for illegal trapping on the Rat River, Constable King of the RCMP was shot by Johnson, sparking off a long chase that became front-page news across the continent. May was again hired to see if he could find Johnson, who had seemingly disappeared. On February 13 May solved the mystery when he noted a set of footprints leading off from caribou tracks in the middle of the frozen river. Johnson had been following their tracks to hide his own, but had to strike off the path to set up camp at night. Following the trail over the next few days the RCMP rounded a bend on the river on the 17th to find Johnson in the middle of the trail again, unable to dodge for the bank without his snowshoes on. A firefight broke out during which one of the RCMP officers was seriously wounded and Johnson killed. May arrived just after the action ended, and landed beside the injured officer and flew him 125 miles to a doctor, being credited with saving his life.
These actions were later heavily fictionalized in the 1981 movie Death Hunt. The movie shows May as a fictional RCAF "Captain Tucker" firing wildly at everyone on the ground, including the posse, who fire back and cause him to crash into a mountain.
While this was going on the United States was also ferrying huge numbers of aircraft to the Soviet Union, flying through Edmonton on their way. A number of these crashed due to mechanical problems, in which case there was no way for an injured pilot to get out of the "back country" when this happened. The idea came up that a team of parachute jumpers should be formed that could be dropped in on the crash sites to stabilize the injuries and start moving the pilots out of the bush. Early efforts were comical but dangerous, but the US trained a number of jumpers at a smokejumper school in Montana, and it was not long before the Para-Rescue team was in service. Several additional Para-Rescue teams were set up during the war, and by the time the war ended the value of these teams was recognized. They were soon re-organized into their own command within the Canadian military, Search and Rescue. For his work in Search and Rescue, May was awarded the Medal of Freedom, with Bronze Palm in 1947 by the USAAF.
In addition to the DFC and the United States Medal of Freedom, Wop May was awarded the Trans-Canada (McKee) Trophy in 1929 and became an Officer in the Order of the British Empire in 1935. In 1974 May was declared a National Historic Person, and a plaque to commemorate him was installed in Edmonton in 1978.
On October 6, 2004, NASA's Mars Exploration Rover Opportunity located a rock on the south slope of the Endurance Crater on Mars. The 1 metre (3.3-foot) rock was given the name wopmay after the legendary Canadian bush pilot.
Interestingly, Canada has a geologic feature known as the Wopmay Fault Zone, lying to the west of Hudson Bay along the Wopmay river, where the earliest mountains in earth's history appeared during the Paleoproterozoic era, approximately two billion years ago.