Montgomery’s father worked for Underwood Typewriters in 1902, while also working at a stationary store in Seattle. There was always a typewriter around for him to use.
“I started goofing around with these machines when I was in grade school,” he said. Montgomery was first in charge of putting the ribbon on the typewriters. He learned more complex repairs, but he didn’t initially want to make it a career.
“I had no intention of being a repairman,” Montgomery said. “I really didn’t get seriously involved with fixing typewriters until I got out of the Army.”
He was drafted into the Army during World War II. Wherever he was stationed, folks found out about Bob’s special skill.
“I kept getting steered into it,” Montgomery said of typewriter repair. “It was one of these, ‘Oh, you know how to fix one of these machines? How do you fix this part?’ ”
There was the time he went to Camp Beale, California. “They literally grabbed me by the collar and said, ‘Here’s your repair shop,’ ” he said.
Then there was England, where he got a brief break from typewriters. “I spent almost 10 days as a purchasing agent for Army headquarters,” he said. “But it wasn’t why I came to them in the first place. I came to them to fix typewriters.”
Then Versailles, and then Frankfurt, making sure military communications typed smoothly.
Kitsap lacked a steady repairman at the end of the war, so he thought it was a good place to set up shop with his father. His business was strictly local at first. “By 1955 some of the old-timers were getting to old to do it anymore,” Montgomery said.
Montgomery remembers repairing typewriters during World War II in Bushy Park in London, right where Gen. Dwight D. Eisenhower was stationed as the Supreme Commander Allied Expeditionary Force. A few times, Montgomery saw Ike going to and fro.
Wars generate not just casualties, but plenty of paperwork. Montgomery had been drafted and trained as an infantryman.
Then his records showed he could repair typewriters.“I think every latrine orderly had a typewriter,” he remembers.