A Choose Your Own Obituary

A man whom I’ve never met but to whom I owe a debt has passed away: R.A. Montgomery, pioneer of the “Choose Your Own Adventure” kid’s book series that is at least partially to blame for my own adult zombie choose-your-own-adventure-style book, Undead Rising. Like just about every other kid who has run across them, I loved those books, and his career–and the way he was heavily involved in his work, even having a stake in all of the 230 books published in the line.

While I and a great many other child readers were sad to hear of Mr. Montgomery’s passing, we were also a little disappointed in his official obituary, because it isn’t in the iconic format he pioneered. Seeing as I have experience both in writing obituaries (which are, by the way, strangely pleasant to write: it’s all the best parts of a person’s life) and in writing gamebooks, I thought I’d give it a shot in revising it.

With complete respect and gratitude for this innovator, I present a revised Choose Your Own Obituary.

Raymond Almiran Montgomery, original publisher and author of the incredibly popular Choose Your Own Adventure book series for children, died in his home in Warren, Vermont, on Sunday, November 9. He was 78 years old. But Mr. Montgomery had a life full of adventures, including:

an illustrious educational career
solving challenging puzzles
world travels
Jump ahead to the parts about CYOA, because you don’t like reading much about obituaries, even Choose-Your-Own-Adventure ones.

Mr. Montgomery, known to friends as Ray, attended Hopkins Grammar School, Williston Academy, and graduated from Williams College in 1958. He attended Yale Divinity School for a time before joining The Wall Street Journal, where he promoted the Journal as a learning tool in classrooms. He was so sensational he became the Assistant Dean of Faculty at Columbia University from 1963 to 1965. And that wasn’t enough! He then founded the Waitsfield Summer School in Waitsfield, Vermont, in 1966. It offered a revolutionary program aimed at children with learning challenges, in which an English curriculum was experience-based and gaming was used exclusively to teach basic math.

Return to the beginning to learn more.
Learn about Montgomery’s family life.

In 1969, Mr. Montgomery joined the famous Clark Abt Associates think tank. Abt’s book Serious Games published in 1970, analyzed the effectiveness of role-playing for problem-solving, which significantly influenced Mr. Montgomery. He then developed a role-playing game for the Edison Electric Institute entitled The Energy Environment Game. The game encouraged students to take roles in solving the problem of the scarcity of energy resources. It was then widely used in high schools across the country during the real-world energy crisis of 1971.

In case that wasn’t enough, he also created numerous games used to train Peace Corps volunteers about cultural awareness and sensitivity.

Montgomery tackles the puzzle of technology.
Montgomery becomes a pioneer in publishing.

World Travel
Mr. Montgomery was not a man to be contained. He left the Yale Divinity School after only a year of study after his pursuits skiing and mountain climbing. But that didn’t slow him down. He traveled frequently to West and North Africa to develop training materials for the Peace Corps.

However, despite all that, Mr. Montgomery stayed close to his beloved Vermont for much of his life.

Return to the beginning to learn more
Learn about Montgomery’s family life.

Family Life

With a young family growing up in Vermont, Montgomery wanted to work closer to home. So he co-founded Vermont Crossroads Press with his first wife, Constance Cappel, in 1975.The marriage lasted a few years before they divorced in 1977.

He later remarried, and with his wife Shannon Gilligan created a creativity tool for kids.

Montgomery is survived by his wife, Shannon Gilligan of Warren, Vermont; his son, Anson Montgomery of Playa Flamingo, Costa Rico, and daughter-in-law Rebecca Montgomery; granddaughters Avery and Lila Montgomery; and his sister, Joyce Hobson of Portland, Oregon. His son Ramsey Montgomery III died in 2008.

Read more on R.A.’s life:
With his first wife
With his second wife.

Pioneer Publisher

His press, Vermont Crossroads Press, was initially meant to focus on publishing high-quality books for young readers. But Montgomery soon found numerous other books worthy of publication. He bought the first political thriller by novelist Doug Terman, The 3-Megaton Gamble, which was pulled from the warehouse before shipping so that Scribner’s could officially publish it as First Strike in 1978. He also published The Centered Skier by Automative Hall of Famer Denise McCluggage. McCluggage’s book mixed elements of sports psychology with Zen Buddhism and became the basis for several skiing teaching programs around the country. Mr. Montgomery also published The Woodburner’s Encyclopedia, which became a bible to many in search of alternative sources of energy in cold climates. The title sold over 100,000 copies, which was a signal achievement for such a small press.

But publishing was not the end of Montgomery’s literary career:
Would you choose your own adventure?
Discover how ghosts affected Montgomery’s path.

Choosing His Own Adventures

In 1977, an author named Ed Packard approached Montgomery about publishing his interactive children’s book Sugarcane Island. The young publisher saw it for what it was: a role-playing game in book form and eagerly put it in print. He felt so confident about it that he announced it as the first in a series entitle The Adventures of You. When Packard left Vermont Crossroads Press to write his next book for Lippincott, Montgomery wrote the subsequent book–Journey Under the Sea–and published it under the pen name Robert Mountain. When his marriage ended in divorce a short while later, Montgomery sold his interest in the press to his ex-wife and brought The Adventures of You” to Bantam Books, which was looking for something “different” with which to inaugurate a new children’s book division. Bantam offered Montgomery a contract for Journey Under the Sea along with five more untitled books and renamed the series “Choose Your Own Adventure.” Little did Bantam or Montgomery realize that a publishing legend was about to be born. “Choose Your Own Adventure” went on to sell more than 250 million copies across more than 230 titles in over 40 languages, making it the 4th bestselling series of children’s books in the world.

“I have edited and published hundred’s of children’s books, but overseeing CYOA at Bantam was the high point of my long career. I knew at the time that the series was making a major contribution to literacy, and that was immensely rewarding,” notes Ron Buehl, former VP and Editor-in-Chief of Bantam Books.

After the first two CYOA contracts, Ray shared the writing responsibility for the series evenly with Ed Packard.

But how did ghosts affect CYOA?
What is the series up to today?

On Ghosts

From the first contract, Ray opted not to use ghost writers, but to acknowledge every “Choose Your Own Adventure” author by his or her name. This ran counter to the standard publishing practice of the time of crediting all books to the founding author. This signal act helped launch the publishing careers of several young authors, including Doug Wilhelm, Jay Leibold, and Laban Carrick Hill, a winner of the National Book Award. He also invited Ed Packard back to write more books, along with Doug Terman, who wrote under the pen name D. Terman.

Return to the Choose Your Own Adventure series.


Ray Montgomery’s interests extended to new technology. He was an early owner of an Apple II. He helped adapt two “Choose Your Own Adventure” books as games for the Atari console in 1984. Then he was “evangelized” by Apple Computer in 1990 to develop software for CD ROM on the Macintosh. His most notable project from this era was a creativity tool for kids entitled “Comic Creator” that he designed and produced with his wife, Shannon Gilligan. “Comic Creator” was featured as Best New Software in People Magazine in 1995.

Read more about Montgomery’s second wife, Shannon Gilligan.
Close out Montgomery’s triumphant career.

Vs. The Robot King

Montgomery continued to write books for “Choose Your Own Adventure” throughout his career. His final title, Gus vs. The Robot King,was released in September 2014. Montgomery and Gilligan had taken over the series when Bantam Doubleday Dell, now an imprint at Random House, stopped publishing new books in 2000. In 2003, they co-founded Chooseco LLC to relaunch the series. Montgomery, who was passionate about education all his life, felt that interactive fiction was critical to reluctant readers in achieving reading fluency, which is the final state of achieving true literacy. He thus felt it was imperative to keep the books in print. Chooseco has sold ten million copies of 65 CYOA titles in the past nine years. A movie based on Montgomery’s Choose Your Own Adventure: Mystery of the Maya is currently in development at Fox Films.

Missed something? Go back to the beginning
Discover the end.

The End

A private memorial is planned for the spring.

Thank you, Mr. Montgomery, for the gifts of fiction and the love of reading that you’ve shared with so many.

Undead Rising coverMr. Montgomery inspired my book, Undead Rising: Decide Your Destiny, available in print and on Kindle. Much like Montgomery’s Choose Your Own Adventure books, Undead Rising allows you to make choices that will effect the story. Note: This book is great for nostalgic adults, but kids should stick to Montgomery’s works!

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