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Wager with the Wind: The Don Sheldon Story
Don Sheldon has been called 'Alaska's bush pilot among bush pilots', but he was also just one man in a fragile airplane who, in the end, was solely responsible for each mission he flew, be it a high-risk landing to the rescue of others from certain death in the mountains of Alaska or the routine delivery of supplies to a lonely homesteader. Read James Greiner's Wager with the Wind to learn how a hero was born, and also how he made his courageous journey to the unknown skies of dealing with cancer.
256 pages, Paperback
First published January 1, 1974
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Displaying 1 - 30 of 38 reviews
November 10, 2011
Don Sheldon's skill as an Alaskan bush pilot is the stuff of legends. His stories left me gaping with amazement that he survived such harrowing adventures! Try landing on crevasse-ridden high-altitude tiny spots of glacier with swirling winds, or landing on a river and floating backwards though the rapids to reach the stranded Army scouts - three times! The interactions with the Denali mountain climbers is fascinating as well. They came from all over the globe and faced incredible adversity and weather - just as Sheldon did when he initially dropped them off on the mountain, picked them up after an ascent, or had to rescue them! Don Sheldon is a pilot's pilot and a hero. Read the book!
May 1, 2025
James Greiner's book on Don Sheldon,the famous bush pilot is a must read for anyone with an interest in Alaska, Moutaineering or general aviation, particularly small plane bush flying in the period of the last 80 or 90 years especially in the post war period when Alaska was a territory. This book was published in 1974 when Don was still extremely busy running his Talkeetna Air Service and the author and probably Don himself were probably unaware that Don's time on earth would soon be coming to an end. In early 1975 Don Sheldon died of colon cancer at the young age of 53.
Don left a small ranch near Lander Wyoming after both of his parents died unexpectedly in the midst of the great depression arriving in the raw and wild Alaska territory penniless but embracing the challenge to start a life on the ground floor in a state which was doing the same thing. He took a poor paying job in Anchorage at a dairy farm working as he said 7 days a week and 16 hours a day for $40/month. The largest city in Alaska had dirt streets and only 2500 souls but in a short time the ranch boy from Wyoming was ready to leave the big city for better opportunities and he hopped on the Alaskan Railroad and landed in the tiny mining town of Talkeetna. He took the first job he could find, cutting wood but then tried his hand at trapping and then backbreaking gold mining. Early on he cast his eyes upward at the rare sight of the bush planes and resolved that he was going to learn to fly. He said "all he could think was how much better that kind of travel in this area of no roads was than beating beating yourself to death on a pair of snowshoes." He saved his pennies and enrolled at an engineering program in Fairbanks. After a few semesters he was not any closer to getting in a cockpit and he set off to the interior lured by big money in trapping and then construction which was to fund his flight instruction in late 1940 back in Anchorage. He enrolled at Lars Larson's flight school at Merril Field and received his private license in early January 1942, just after the bombing of Pearl Harbor. Like many young men he was a recently trained pilot and eager to join the fight against the Japanese and the Nazis, preferably as a fighter pilot, the glamour job de jour. Off he went to Seattle with other young men like my pilot father of similar aspirations but the Air Corps needed bomber crews. He landed in England as crew of a B-17 bomber surviving 26 missions over Germany despite two crash landings back in England. After he was discharged he returned to Talkeetna with his nest egg from saving his flight pay with the goal of starting up a flying service. The biography really picks up from there with how he started and built up his business developing new ways to make bush flying pay supplying bush businesses as well as hunters and fishermen and miners . A new opportunity was providing flying support to mountain climbers in the adjacent Alaska Range. Don was one of the first to develop the technology and techniques of mountain and glacier landings and takeoffs and the author does a splendid job of how was able to thrive and survive these early perilous exploits. The bulk of the book tells of these thrilling and even astounding feats and if you are a pilot these tales will be like raw meat to you. A large section of the book centers around Mt McKinley only 60 miles to the north of Don's airfield in Talkeetna, and Don was not just important in delivering mountain climbers to the giant mountain but also many search and rescues which were hair raising and dangerous.
Wager the Wind is out of print and over 50 years old but you will be well rewarded if you can secure a copy. I purchased my copy brand new in 1974 and still have it complete with dust cover. I recently re read it. Now I have a disclaimer. I bought the book because I had met Don Sheldon and flew with him on multiple occasions into and out of Denali in 1969 when I was a climber and a scientific researcher with Institute of Arctic Biology of the U of Alaska Fairbanks. I flew with him on an off the Kahiltna and Ruth glaciers as well as his tiny landing patch at 14300' by the West Buttress. I spent many an hour with our team tramping that steep slope on snowshoes so he could fly in and out. Don Sheldon was one of those bigger than life heroes of the high mountains of Alaska. This was a 5 star book for me but I am biased of course. I am lucky to have spent time with him and I grieved his passing 50 years ago. I still have a pair of his snowshoes on the wall of our log cabin.
Don left a small ranch near Lander Wyoming after both of his parents died unexpectedly in the midst of the great depression arriving in the raw and wild Alaska territory penniless but embracing the challenge to start a life on the ground floor in a state which was doing the same thing. He took a poor paying job in Anchorage at a dairy farm working as he said 7 days a week and 16 hours a day for $40/month. The largest city in Alaska had dirt streets and only 2500 souls but in a short time the ranch boy from Wyoming was ready to leave the big city for better opportunities and he hopped on the Alaskan Railroad and landed in the tiny mining town of Talkeetna. He took the first job he could find, cutting wood but then tried his hand at trapping and then backbreaking gold mining. Early on he cast his eyes upward at the rare sight of the bush planes and resolved that he was going to learn to fly. He said "all he could think was how much better that kind of travel in this area of no roads was than beating beating yourself to death on a pair of snowshoes." He saved his pennies and enrolled at an engineering program in Fairbanks. After a few semesters he was not any closer to getting in a cockpit and he set off to the interior lured by big money in trapping and then construction which was to fund his flight instruction in late 1940 back in Anchorage. He enrolled at Lars Larson's flight school at Merril Field and received his private license in early January 1942, just after the bombing of Pearl Harbor. Like many young men he was a recently trained pilot and eager to join the fight against the Japanese and the Nazis, preferably as a fighter pilot, the glamour job de jour. Off he went to Seattle with other young men like my pilot father of similar aspirations but the Air Corps needed bomber crews. He landed in England as crew of a B-17 bomber surviving 26 missions over Germany despite two crash landings back in England. After he was discharged he returned to Talkeetna with his nest egg from saving his flight pay with the goal of starting up a flying service. The biography really picks up from there with how he started and built up his business developing new ways to make bush flying pay supplying bush businesses as well as hunters and fishermen and miners . A new opportunity was providing flying support to mountain climbers in the adjacent Alaska Range. Don was one of the first to develop the technology and techniques of mountain and glacier landings and takeoffs and the author does a splendid job of how was able to thrive and survive these early perilous exploits. The bulk of the book tells of these thrilling and even astounding feats and if you are a pilot these tales will be like raw meat to you. A large section of the book centers around Mt McKinley only 60 miles to the north of Don's airfield in Talkeetna, and Don was not just important in delivering mountain climbers to the giant mountain but also many search and rescues which were hair raising and dangerous.
Wager the Wind is out of print and over 50 years old but you will be well rewarded if you can secure a copy. I purchased my copy brand new in 1974 and still have it complete with dust cover. I recently re read it. Now I have a disclaimer. I bought the book because I had met Don Sheldon and flew with him on multiple occasions into and out of Denali in 1969 when I was a climber and a scientific researcher with Institute of Arctic Biology of the U of Alaska Fairbanks. I flew with him on an off the Kahiltna and Ruth glaciers as well as his tiny landing patch at 14300' by the West Buttress. I spent many an hour with our team tramping that steep slope on snowshoes so he could fly in and out. Don Sheldon was one of those bigger than life heroes of the high mountains of Alaska. This was a 5 star book for me but I am biased of course. I am lucky to have spent time with him and I grieved his passing 50 years ago. I still have a pair of his snowshoes on the wall of our log cabin.
December 19, 2020
Before he started flying lessons, my dad bagged Don Sheldon's groceries when he came into Anchorage. He always tipped despite Safeway's policy against it. That is my tenuous third-person connection to the romance and daring of Alaska's wilder frontier days.
This book was obviously written by a big fanboy. There is not the tiniest breath of criticism. I'm not an airplane person, but there are stories in here like, damn, even *I* can tell this was a completely unnecessary risk to take. Enough so, it made me wonder if having lost his parents as a child and flown a bunch of combat missions in WW2—maybe Don gave less weight to the importance of staying alive. Author says more than once that Don Sheldon prided himself on never having lost a passenger (loads of wrecks though!) and also, that seems like a low standard?? Then again, flying was pretty nuts back then.
Fun read for all the Alaska history. Amazing how much flying he did on Denali with climbers, and how much death he saw because of it. Lots of folks "assaulting" and "attacking" the mountain from new angles, in new seasons, and then falling into crevasses or freezing to death in a storm etc., etc. What a weird nihilistic hobby.
This book was obviously written by a big fanboy. There is not the tiniest breath of criticism. I'm not an airplane person, but there are stories in here like, damn, even *I* can tell this was a completely unnecessary risk to take. Enough so, it made me wonder if having lost his parents as a child and flown a bunch of combat missions in WW2—maybe Don gave less weight to the importance of staying alive. Author says more than once that Don Sheldon prided himself on never having lost a passenger (loads of wrecks though!) and also, that seems like a low standard?? Then again, flying was pretty nuts back then.
Fun read for all the Alaska history. Amazing how much flying he did on Denali with climbers, and how much death he saw because of it. Lots of folks "assaulting" and "attacking" the mountain from new angles, in new seasons, and then falling into crevasses or freezing to death in a storm etc., etc. What a weird nihilistic hobby.
August 4, 2019
One of the BEST Aviation books I have ever read, and I’ve read a lot of them.
For those of you that have read Don Dwiggens, HOLLYWOOD PILOT, or FATEFUL RENDEZVOUS, by Steve Ewing and John Lundstrum, you are in for a treat. Don Sheldon was a pilot whose skill was extraordinary. He was the kind of man who cared deeply for others, to the point he would risk his own life to save the lives of others. This is the bush pilot who perfected the art of Glacier landings. Any pilot knows that the quickest way to gain the experience necessary for a job with a major carrier is to become an Alaskan Bush pilot. He made a career of it while for others, it is only a stepping stone. A consummate professional with an astounding safety record. A pilots pilot. I’ve read about people who say he does not deserve the alleged lionizing of this book. However, if you read it, I think you will find it is about a man who loved to fly, loved Alaska, and and was very humble about it. Inspiring.
For those of you that have read Don Dwiggens, HOLLYWOOD PILOT, or FATEFUL RENDEZVOUS, by Steve Ewing and John Lundstrum, you are in for a treat. Don Sheldon was a pilot whose skill was extraordinary. He was the kind of man who cared deeply for others, to the point he would risk his own life to save the lives of others. This is the bush pilot who perfected the art of Glacier landings. Any pilot knows that the quickest way to gain the experience necessary for a job with a major carrier is to become an Alaskan Bush pilot. He made a career of it while for others, it is only a stepping stone. A consummate professional with an astounding safety record. A pilots pilot. I’ve read about people who say he does not deserve the alleged lionizing of this book. However, if you read it, I think you will find it is about a man who loved to fly, loved Alaska, and and was very humble about it. Inspiring.
May 7, 2021
Overall enjoyable read. Don Sheldon lead a very interesting life according to the book and many of his adventures (which were apparently routine to him) are chronicled here. A great read for any outdoorsman or anyone interested in the modern-day frontier.
Sheldon himself is quoted in the book that some of the stories may have been exaggerated (as tales told from memory often are), but nothing about the book seems outright false or misleading. Towards the end, though the stories and accounts are all exciting or interesting, the book does begin to feel like a laundry list of stories rather than a single running narrative, but not so much that I lost interest.
Overall, a good read and a book I would recommend to others. It also mentioned several similar books about mountaineers and similar topics that I will be reading in the future.
Sheldon himself is quoted in the book that some of the stories may have been exaggerated (as tales told from memory often are), but nothing about the book seems outright false or misleading. Towards the end, though the stories and accounts are all exciting or interesting, the book does begin to feel like a laundry list of stories rather than a single running narrative, but not so much that I lost interest.
Overall, a good read and a book I would recommend to others. It also mentioned several similar books about mountaineers and similar topics that I will be reading in the future.
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February 15, 2021I'm biased because Don Sheldon was a distant relative of mine. I had heard stories but was too young to ever meet him -- if he ever came to the lower 48 that is. This was true pioneer stuff in Alaska as it still is for many people. Sheldon and others were truly breaking new ground, or opening up new skies. The tales of flying on low gas, dropping pin boughs to the snow covered ground below because there is nothing else for scale keep you on the edge of your seat. The man and his friends had many a close scrape and some didn't make it. There is very little pioneer spirit left, unless we count Elon Musk. More like we just don't hear about it. Don Sheldon just went out and did it without a lot of talk. This is something we need to get back to.
April 16, 2023
Overall was a good book with some great stories about Sheldon and mountaineering on Denali. It’s amazing to hear some of these stories of Don just doing incredible stuff, it’s unbelievable that he survived all these amazing feats as a pilot doing some stuff that is probably still unparalleled today.
If they ever re-print this book, it needs to be combed thru for some word changes, like Denali for McKinley and using Native Alaskans. And there’s a few others, that maybe when written in the late 70s were ok, but it could just be update, there’s a couple cringey phrases in this book. Don’t think they were used for ill intent but could be updated for sure.
If they ever re-print this book, it needs to be combed thru for some word changes, like Denali for McKinley and using Native Alaskans. And there’s a few others, that maybe when written in the late 70s were ok, but it could just be update, there’s a couple cringey phrases in this book. Don’t think they were used for ill intent but could be updated for sure.
February 13, 2019
Loved the overall concept and story of Don Sheldon, first real Alaskan bush pilot, father of mountain aviation, and hero to climbers everywhere, but found the writing style choppy, incomplete, and lacking a narrative arc. Pieces of the book were fascinating and would have been really interesting to read in an expanded format, but other pieces of the book were very much presented as “this happened, then this happened, then this happened”. I can understand how this was a bestseller at the time, but the story could really use a historical refresh. It’s too bad this legend is no longer with us.
May 22, 2020
a classic example of a subject larger than the book .
Sheldon was clearly a legend and a pioneer in aviation and the stories told here are incredible but the author comes across as more of the friend who remained to tell the tale than the true biographer Sheldon deserves.
Nevertheless, an excellent read. just the section on Devils Canyon alone is worth the price of admission, especially if you know anything about small plane aviation or whitewater river rafting. I know about both and i'm not sure anyone has ever combined the two like Sheldon. incredible.
Sheldon was clearly a legend and a pioneer in aviation and the stories told here are incredible but the author comes across as more of the friend who remained to tell the tale than the true biographer Sheldon deserves.
Nevertheless, an excellent read. just the section on Devils Canyon alone is worth the price of admission, especially if you know anything about small plane aviation or whitewater river rafting. I know about both and i'm not sure anyone has ever combined the two like Sheldon. incredible.
February 11, 2021
The man himself was apparently quite the character, and the events he partook in must have been a roaring adventure. But regrettably, I didn't feel I got to know the person during the course of this book, and while I read *of* his adventures, I did not get to take part in them. Somehow I failed to connect with this book, and felt like the truly interesting story was told between the lines more than in them.
March 21, 2023
A fascinating book
A fascinating book about the flying experiences of Don Sheldon in Alaska, especially around and on the great mountain Denali. As a retired military pilot and a civilian pilot of 49 years, I found the flying details of this story to richly enhance the book. Several months ago I was able to visit Alaska for the first time and was able in reading this book to relive some of my experiences there. A great read!
A fascinating book about the flying experiences of Don Sheldon in Alaska, especially around and on the great mountain Denali. As a retired military pilot and a civilian pilot of 49 years, I found the flying details of this story to richly enhance the book. Several months ago I was able to visit Alaska for the first time and was able in reading this book to relive some of my experiences there. A great read!
April 6, 2025
I thoroughly enjoyed reading Wager With The Wind. The unique stories that compose Don Shelton's life, paired with the vivid imagery painted by the author, creates an exciting reading experience. This book is able to fit a lot of short stories into a relatively small page count. While this allows Wager With The Wind to be not too long of a read it creates some confusing chronology of events, and results in stories that can feel interrupted at times.
January 20, 2022
I enjoyed the book, since I have flown quite a bit in Alaska. Don Sheldon is one of the most famous bush pilots of his time. I was disappointed the book really did not do justice to him. It was rather disorganized and could have been better put together.
August 25, 2017
The information is interesting (although the facts behind the NOLS situation in 1972 are largely incorrect, including the school's name...). The writing is adequate but not luminous.
February 8, 2021
Inspirational
May 23, 2022
A good read for alpinists, aviators and all lovers of adventure.
March 15, 2023
Excellent book
A book I did not want to put down. Makes you want to strive to be a man like him. I don't review many books but had to brag on this one. Thanks Jim.
A book I did not want to put down. Makes you want to strive to be a man like him. I don't review many books but had to brag on this one. Thanks Jim.
June 21, 2025
Excellent book. A must read for anyone interested in reading about bush pilots in Alaska.
December 13, 2013
After seeing footage of some amazing bush flying where highly skilled flyers land and take off from some pretty gnarly places, I had a scout around to see if there were any books about this sort of thing. I was compelled to purchase this book as it came highly recommended. I can say that the book is well written and about a pretty incredible bloke who I reckon I would have liked if I'd have known him. However, the author spends the majority of the pages on describing the mountaineering expeditions that Don Sheldon flew support for. Interwoven through this are some really good flying tales and stories about incredible high-altitude mountain rescues, stormy lake landings (and crashes), soaring mountain thermals and the various trials and tribulations of this hugely hazardous flying, but I learned more about the mountain climbing than I did the flying. This really disappointed me, as I thought I was going to read about lots and lots of bush flying. The flying yarns are good, but these seem to take second place to the stories of the people that Sheldon flew around Alaska on various adventures. All that said, I still got a sense of the man and his trade, but not enough. Overall an okay read, but would be at least four stars if the flying stories took centre stage instead of the climbers. Don Sheldon was clearly an amazing man and a massively skilled pilot, but I'm not sure this book does him justice. Sorry Mr Griener, because you do write very well.
August 23, 2014
Charles Kuralt told about Don Sheldon flying him and cameraman Izzy Bleckman up to Ruth Glacier and having them spend a night in a remote cabin with a Roman Catholic priest who was there on a retreat of solitude. After a month alone the priest welcomed them heartily and at the evening's end they spent much of the night outside watching the spectacular display of Aurora Borealis. Kuralt surmised that Sheldon had sized them up as a couple guys in too much hurry who could use a taste of remote Alaska.
Wager with the Wind is the story of Alaska bush pilot Don Sheldon. Although it lacks the pear-shaped resonance of a Charles Kuralt piece, Greiner has produced a biography that does his subject justice throughout. He doesn't overstate Sheldon's skill and courage but still he puts across the extreme conditions bush pilots face and the comprehensive knowledge needed in order to survive and complete their missions. Sheldon's understanding of his environment was encyclopedic and he used it routinely in the least routine flying one could conjure. You needn't be a pilot to understand and appreciate this book but if you are a pilot you'll have an even greater appreciation for Sheldon's achievements. Five stars for the story, three for the writing and heartfelt thanks to Charles Kuralt.
For those who are away from Alaska and who want to learn about it I recommend just two books: Coming into the Country by John McPhee and Wager with the Wind.
Wager with the Wind is the story of Alaska bush pilot Don Sheldon. Although it lacks the pear-shaped resonance of a Charles Kuralt piece, Greiner has produced a biography that does his subject justice throughout. He doesn't overstate Sheldon's skill and courage but still he puts across the extreme conditions bush pilots face and the comprehensive knowledge needed in order to survive and complete their missions. Sheldon's understanding of his environment was encyclopedic and he used it routinely in the least routine flying one could conjure. You needn't be a pilot to understand and appreciate this book but if you are a pilot you'll have an even greater appreciation for Sheldon's achievements. Five stars for the story, three for the writing and heartfelt thanks to Charles Kuralt.
For those who are away from Alaska and who want to learn about it I recommend just two books: Coming into the Country by John McPhee and Wager with the Wind.
October 16, 2023
I was riding in a bus down the twists and turns of the park road in Denali when I heard Don Sheldon's name the first time. He's someone synonymous with Alaskan aviation and Mt.Denali itself.
The stories in this book reinforce that he was an extremely rare person. Someone good enough to put themselves directly in harm's way again and again for people he barely knew, while also being lucky enough to survive. On top of that, his natural charsima made him somewhat of a real-life superhero.
While Sheldon is amazing and I seriously miss Alaska, the writing in this book wasn't as great. Feels like a collection of stories rather than a cohesive book. The author uses the same literary devices to add thrill or humor. Falls flat sometimes.
The stories in this book reinforce that he was an extremely rare person. Someone good enough to put themselves directly in harm's way again and again for people he barely knew, while also being lucky enough to survive. On top of that, his natural charsima made him somewhat of a real-life superhero.
While Sheldon is amazing and I seriously miss Alaska, the writing in this book wasn't as great. Feels like a collection of stories rather than a cohesive book. The author uses the same literary devices to add thrill or humor. Falls flat sometimes.
May 20, 2011
It is, admittedly, difficult for me to not rate books on aviation rather highly, as I enjoy all of them. The author was a friend of the late Don Sheldon, a legend in his own time, further supported by the acclaim afforded him by his peers, the U.S. military and his hundreds of customers who relied on him to get them in and out of wild Alaska wilderness. Sheldon cheated death many times throughout his life as a bush pilot and has to be one of the luckiest men alive to have survived so many harrowing situations, not just one. This was an easy read and the author had left a fine example of Sheldon's legacy in this book.
September 7, 2012
This was a great story about an amazing, and lucky, bush pilot. Don Sheldon was instrumental in making some of the most historical climbs happen. I had not realized he did the flying for the first ascents for Mt Huntington and the Cassin Ridge. This biography has triggered me to want even further into some of the other tales in the Alaskan ranges.
At one time I thought being a bush pilot would be fun. After reading this I am glad I did't get to even try. I cannot imagine crashing the planes he did and walking away from them every time.
Don Sheldon is missed and his knowledge of Denali left a gap in the world that I am not sure can ever be built back up.
At one time I thought being a bush pilot would be fun. After reading this I am glad I did't get to even try. I cannot imagine crashing the planes he did and walking away from them every time.
Don Sheldon is missed and his knowledge of Denali left a gap in the world that I am not sure can ever be built back up.
July 6, 2015
Fantastic biography of Don Sheldon - Alaskan bush pilot extraordinaire. The true stories of his rescues of mountain climbers on Denali and trappers and other crash victims were amazing. He'd land his Super Cub on tiny stretches of glaciers or in short lakes and raging rivers. The Alaskan weather is incredibly cold but also unpredictably stormy in the mountains. He also flew Cessna 180s, which he ordered without paint to keep the weight down... He had his share of crashes but managed to survive them all, even when he was stranded in the winter for days and had to unearth the airplane from constantly falling snow. Sadly he died of cancer at 53 in the 1980s.
August 23, 2009
I read this book as part of my research for a college paper. I generally enjoy reading about the earlier days of aviation, and the challenges met in Alaska, so I found this story educational as well as fascinating, even spell-binding. Don Sheldon was one of first pilots attempting to fly mountaineers and others to Denali, which is very high altitute mountain flying for a small plane.
September 3, 2015
I found Don Sheldon's story to be fascinating. He was a truly gifted and brave pilot in the most grueling conditions. Having been to Talkeetna made the book all the more interesting. The only reason I didn't give it 4 stars is because at times the detailed descriptions of the airplanes was a bit much. However, any pilot who reads this would love that part.
January 25, 2011
Very good descriptions a things that really happened... Don Sheldon dies before my time in AK but I had always heard about him as an amazing bush pilot & guide. The book came out not long after his death and I don't know why I didn't read it years ago.
December 8, 2012
It's a true five star book, especially for pilots and those familiar familiar with Alaska's bush. I think the craziest story was of Sheldon and a fur buyer, flying around northern Alaska in the dead of winter (the dark) on a fur buying trip in a Super Cub.
May 15, 2008
Very good biography about one of the original Alaska Bush Pilots. This guy was fearless and actually landed at 14000 feet on Mount McKinley. Amazing.
February 2, 2010
A great story about the life of an Alaskan bush pilot. If you enjoy aviation and the great outdoors, you'll enjoy this book!
Displaying 1 - 30 of 38 reviews