Glyndon L. ‘Glyn’ Bailey, a retired Chessie System — now CSX Corporation — executive whose career spanned four decades, died Aug. 22 at the University of Maryland St. Joseph Medical Center. The Towson resident was 101.

“Glyn was a great guy. Hardworking and reliable,” said E. Ray Lichty, a retired CSX executive, longtime colleague and friend. “Tough but fair.”

Glyndon Leslie Bailey, son of Leslie Bailey, an A&P grocery store manager, and Catherine Bailey, a homemaker, was born in Baltimore and raised in Catonsville.

He began his lengthy railroad career with the B&O Railroad in 1940 in the freight office at Camden Station after graduating from Mount St. Joseph High School in Irvington.

During World War II, he served in an Army ordnance unit from 1943 to 1945 and obtained the rank of sergeant.

Mr. Bailey, who was known as Glyn, was promoted to traveling auditor in 1951, and from 1954 to 1956, he was assigned to Columbus, Ohio, before returning to Baltimore and settling in Catonsville.

He was a traveling auditor responsible for covering the B&O’s eastern territory, and in 1962, he was named chief traveling auditor.

After all freight accounting offices were consolidated into zone accounting offices, Mr. Bailey was put in charge as auditor of all the bureaus.

“As a traveling auditor back in the 1940s and 1950s, he would ride steam-powered trains all over his territory to check the records and ensure all was well and the cash was properly handled,” Mr. Lichty explained in an email. “One day it might be a train to Oakland for a few days and then off to Aberdeen for another review.”

At the time, Mr. Bailey didn’t own a car and commuted to work at the B&O’s headquarters in downtown Baltimore by streetcar.

“When they did audits for a large station, such as the ticket office in the B&O Building, a team would arrive after the office closed for the day and work all night checking the paperwork and the handling of cash and tickets, finishing up in time to open the next morning,” Mr. Lichty wrote.

“When I came to the B&O in 1954, I met him on my first day. Glyn was my assistant director,” said Diane Homburg.

“He was a true gentleman who never spoke a harsh word,” she said. “He was a great boss and fair, and he never played favorites, but fair bosses can’t always be popular,” said Ms. Homburg, who retired in 2009 from CSX where she was a computer programmer. “We became great friends and I was so glad to have known him.”

In 1975, Mr. Bailey was promoted again to auditor-accounts receivable, and finally to director of customer accounting, a position he held until retiring in 1980.

After undergoing bypass surgery in 1990, Mr. Bailey joined The Mended Hearts Inc., a support group for those who had undergone heart surgery.

In retirement, he and his wife, Mary Jeanne Bailey, whom he married in 1943, moved to Myrtle Beach, South Carolina, and then returned to Maryland in 1999.

He later became assistant regional director of Mended Hearts and established chapters in hospitals in Baltimore; Wilmington, Delaware; Myrtle Beach and Orangeburg, South Carolina. He also volunteered at LifeBridge Health Sinai Hospital.

He was a member and past president of RABO, a CSX retirees organization.

He was an avid model railroader.

His wife of 72 years died in 2015.

Mr. Bailey was a communicant of the Roman Catholic Church of the Immaculate Conception in Towson, where a Mass of Christian Burial was offered Aug. 28.

He is survived by a son, Thomas M. Bailey of Louisville; a daughter, Mary Jo Rodney of Towson; four grandchildren; and nine great-grandchildren.