In 2003, he received the National Book Critics Circle Award and the Chicago Tribune's Heartland Prize for Sons of Mississippi: A Story of Race and Its Legacy.

From age 14 to 21, Hendrickson attended Missionary Servants of the Most Holy Trinity Catholic seminary in Alabama, intent on preparing for the priesthood.

[7] In 1977, Hendrickson joined the staff of The Washington Post as a feature writer and reporter for the newspaper's Style section, covering culture and the arts.

[7] When he was working on staff at The Washington Post, Hendrickson began facilitating nonfiction writing workshops at the University of Pennsylvania.

[7] As of 2014[update], Hendrickson has written five nonfiction books, including a memoir and biographies about Marion Post Wolcott, Robert McNamara, and Ernest Hemingway.

The first part of the book examines each of the sheriffs individually, in relation to their families and their home counties, and in the context of the segregated ("totalitarian") society of the time in Mississippi.

While Hendrickson reportedly spent seven years writing the book, he began informal research in 1980, when he met Ernest Hemingway's younger brother, Leicester on a seaplane flight to the Bahamas.

During their vacation in the Caribbean, Hendrickson and his wife had the opportunity to spend time with Leicester Hemingway, while researching and learning about the life of the deceased author.

Seven years later, while Hendrickson was at The Washington Post, he began an in-depth two-part series for the newspaper, which focused on the lives of author Hemingway's three children.

Based on his 1980 Bahamas research and personal encounter with Leicester, along with the Hemingway series for the Post, Hendrickson eventually began writing his book.

[14] According to Allan Massie in The Wall Street Journal, Hendrickson spent at least 30 years contemplating the life of Hemingway, prior to writing his book.

Howell Raines of The Washington Post in his review of the work stated that "in the academic field of Hemingway studies, the book will stand as an indispensable document".

"[19] In her review of Hemingway's Boat, she reflects on his style of writing as "twists and turns through time, moving sensitively between the books and life.