Killer Konen’s Secret Life

The bombardier’s an instructor now and desperate to win back Shirley.  Learn snippets of how their life ended up together. 

Transcript

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Second Lieutenant Ray Conan leans over a sheet of military issues stationary on March twenty third, nineteen forty-three, ink pooling at the tip of his pen as he writes to Shirley Rutledge about his bouts of jealousy, or as he calls it, the green eyes. This single letter is one of two hundred dispatches Ray sent to Shirley from stateside Army Air Forces training bases during the Second World War. The letters offer a vivid, unvarnished window into the emotional turbulence of a young bombardier instructor wrestling with romance and military pressure long before he would trade the skies for a quiet life, building cabin cruisers and his Oak Park garage and navigating the saloon lined shores of the Illinois Chain of Lakes. But in the spring of 1943, the water and the wood are decades away. Ray is trapped in the rigid, high-stakes machinery of the wartime aviation pipeline, and his mind is entirely consumed by a girl back in Chicago. He is trying to fix a mistake. He writes, I wish I could have seen you this morning, so I could have told you this instead of having to write it. I did something very wrong, and I hope I'm not too late to make it right. Ray is unspooling a raw confession. He admits that he expects things he does not rate, that he is inconsiderate and selfish, that he kept her up late despite knowing how hard she worked. He tells Shirley she has been agreeable, saying swell to whatever he wanted to do, while he was hitting below the belt. He writes, I wanted you to see things my way, and my way is wrong. I'd like to be the kind of guy you'd like me to be, because I think that kind would be nice. The kind of guy I have been isn't nice. The stark vulnerability in his penmanship reveals the intense pressure cooker of stateside military training. In 1943, the Army Air Forces were expanding at a breakneck pace, transforming young men into officers and thrusting them into rapid-fire adulthood. The emotional whiplash of holding life or death responsibilities on the flight line while trying to maintain a civilian romance from a distance cracks through his bravado. He begs her to let him see her once in a while, promising to change, signing off with a declaration of love and the insistence that any good in him exists because of her. One week later, on March 30, Ray writes again The tone shifts from desperate contrition to a more complicated defensive negotiation. Shirley has replied, and her letter has mixed him up. He acknowledges that she sounded off on the beam, and while much of what she said made sense, he is sticking to his guns on certain points. They have differing ideas, but the clash between them is not resolved in a neat Hollywood ending. It is a messy, ongoing collision of two strong-willed individuals. He flatly declares One thing I will say right now, I never will play record fiddle again. Not for you or anyone else. But the rest I'll tell you in person. The phrase record fiddle hangs on the page, a stubborn relic of a specific argument lost to time, yet vibrating with indignation. He challenges her to write down all the things he ever did that she did not think much of, betting she could make quite a list. Yet interspersed with this relational sparring is the harsh, bizarre reality of his daily military duties. He writes I must be one pistol of a teacher. Six students fainted on me in two days. The fellows are all calling me Killer Conan. This casual mention of unconscious cadets points directly to the mechanics of bombardier training in 1943. Training involved immense physical and psychological stress, particularly in altitude chambers. Air crews were subjected to simulated high altitude environments to recognize the symptoms of hypoxia, oxygen deprivation. Instructors like Ray had to ensure students knew how to manage their oxygen masks and recognize their own physical deterioration before passing out. A student sitting in a low pressure chamber would slowly lose cognitive function, their vision narrowing, their coordination slipping. If they did not secure their masks in time, they slumped over unconscious. Ray's moniker, Killer Conan, was born in this brutal, repetitive cycle of testing young men to the point of failure. He is orchestrating simulated near-death experiences by day, then retreating to his bunk to wrestle with his turbulent relationship with Shirley by night. His letters bounce from the physical toll on his students to his battles with military bureaucracy, noting that he had to fight like hell to get three days of leave, securing a furlough from may eighteenth to twenty eighth after being turned down twice. By april nineteenth, the tension between Ray and Shirley seems to have thawed, replaced with the giddy anticipation of a rendezvous. The war's still raging, another snowstorm is floating around, but Ray is planning a weekend in Lansing, Michigan. The sheer excitement spills out in rapid fire typewriter keys. He asks if she can get a Friday and Saturday off to come see him. He's mapping out the dates, promising that his dad thinks it is a good idea, and offering a bribe. Bill promises to buy you a cup of coffee. He paints a picture of their time together, dropping names of local haunts. I'll take you to Tally Ho and the Mayfair, we can walk on the campus in the moonlight, goody goody goody. He even promises to come down to her bank in Chicago after his leave and work two days for free just to help her catch up on her tasks. The contrast between killer Conan, the rigid instructor watching cadets drop from oxidan starvation, and the smitten young man typing goody goody goody over a moonlit walk on a college campus is jarring. It highlights the dual lives led by millions of service members. They were expected to be ruthless instruments of war, yet they clung desperately to the civilian milestones of dates, hamburgers, and starlight. At the bottom of the page, he adds a postscript about his typewriter lacking lowercase letters, finishing with more love, more kisses. Ray Conan survived the war. He made it through the frantic expansion of the Air Forces, the relentless instruction schedules, and the eventual demobilization that sent millions of men flooding back into civilian life. He married Shirley. The intense, fraught letters gave way to the steady rhythm of a shared life. When Ray retired at the age of fifty, he did not dwell on the altitude chambers or the roar of aircraft engines. Instead, he retreated into the quiet, precise world of carpentry. He transformed his garage in Oak Park, Illinois into a makeshift shipyard. The man who had trained eyes to look through a Norden bombsite thousands of feet in the air now trained his eyes on the grain of wood, the curvature of a hull, and the sealant on seam. Over the course of the 1950s, Ray built multiple boats, vessels the size of cabin cruisers, right there in the suburban footprint of Oak Park. Building a boat of that size in a landlocked residential garage requires immense mechanical discipline. It is an exercise in structural integrity and patience. Every rib of the hull must be steamed and bent to a precise degree. The planks must be fastened to withstand the relentless pounding of water and the torque of an outboard motor. For a former bombardier, the process of shaping raw timber into a watertight vessel offered a tangible physical control that the chaos of war never allowed. The smells of sawdust, marine varnish and epoxy replaced the metallic, oil soaked stench of the flight line. When the weekend arrived, Ray, Shirley, and their growing family hitched the massive handcrafted wooden cruiser to their vehicle and hauled it north. Their destination was the Illinois Chain O Lakes. Located near the border of McHenry and Lake counties, the Chain O'Lakes is a vast, interconnected waterway system featuring fifteen separate lakes linked by the Fox River and various man-made channels. It spans over 7,000 acres of water. By the mid-20th century, this sprawling aquatic playground had evolved from a quiet retreat for wealthy Chicagoans seeking Egyptian lotus beds into a bustling, chaotic Mecca for middle class boaters. It was the busiest inland recreational waterway per acre in the United States. To navigate the chain of lakes is to enter a world with its own distinct geography and culture. The water is shared by speedboats, pontoons, fishermen, and massive wooden cruisers like the ones Ray built. The lakes, grass, marie, nippersink, fox, pistaki bleed into one another through narrow, winding channels. The shoreline is densely packed with marinas, resorts, and most famously, waterfront saloons. Eventually, around nineteen sixty eight, the weekend trips were not enough. Ray and Shirley moved to the chain of lakes permanently, trading the dense urban grid of Oak Park for the fluid, shifting boundaries of the water. By this time, Ray's son, Thomas, was growing up on the water, absorbing the mechanical knowledge of his father and the geographical quirks of the chain. It is here, among the interconnected lakes, that the legacy of Ray's meticulous boat building takes on a cinematic quality. Family friends would later recount stories of a ten year old Thomas piloting one of his father's massive hand built cabin cruisers home through the darkness of the chain. Navigating the chain of lakes at night is a dangerous proposition. The water is shallow in many spots, averaging only a few feet in places like Grass Lake. The channels are narrow, the currents from the Fox River are deceptive, and the sheer volume of boat traffic creates a chaotic wake. A captain must know exactly where the sandbars are hidden and where the dredged channels turn. For a ten year old boy to stand at the helm of a heavy wooden cruiser in the pitch black, the mechanical hum of the engine vibrating through the floorboards requires a unique navigation system. Thomas did not use traditional nautical charts or compass headings. Instead, he read the glowing neon signs of the waterfront saloons that dotted the shoreline. The bars of the chain of lakes are legendary institutions, acting as lighthouses for the wayward boater. The most famous among them is Blarney Island, situated a mile off the shore in the shallow waters of Grass Lake. Built on a series of pilings driven into the lake bed, Blarney Island began in the early 1900s after a poker bet between two rival houseboat owners, Jack O'Connor and Shorty Shobin. By the time Thomas was navigating the waters, it was a booming, floating destination, a beacon of light in noise in the middle of the dark water. Other establishments like famous Freddy's Roadhouse, the Broken Oar, and Keefe's Reef formed a constellation of neon along the shores. Thomas would stand at the wheel, his hands gripping the wood his father had shaped and scan the horizon. He would spot the glow of a specific bar sign reflecting off the choppy surface of the lake, align the bow and calculate his heading. When he passed one neon glow, he would adjust his course toward the next, steering the heavy wooden cruiser through the maze of water guided by the ambient light of Midwestern revelry. The boy, the homemade boat, and the glowing saloon signs form a striking contrast to the life Ray Conan lived in 1943, the young bombardier who had written desperate, agonizing letters to Shirley from rigid military bases, who had watched cadets pass out from lack of oxygen, had ultimately engineered a life defined by freedom on the water. The tension of his youth, captured in fountain pen ink and the click clack of a typewriter missing its lowercase letters, dissolved into the steady rhythmic slap of water against a wooden hull. The letters remain, preserved by the family, capturing a man caught in the defining conflict of the twentieth century, desperate to secure the love of a woman in Chicago. The boats he built are likely gone, reclaimed by rot or time, but the story of a father who taught his son how to build something strong enough to carry them home, and a son who learned to navigate the dark by following the lights on the shore endures as a testament to the life Ray and Shirley built after the war was won. If you enjoyed hearing about Ray Cohn's journey from stateside bombardier training to building boats on the chain of lakes, please share this episode with a friend who appreciates history.