After all, the self-described "66-year-old, fat, bald principal" was known for his exuberant school spirit. He once dressed as an Elf on the Shelf and perched himself on top of the school's marquee to celebrate the holidays.
via Virdie Montgomery / Facebook
"I get emotional real easy with my kids," he told WFAA. "And I just didn't feel like I was doing enough. It just seemed like the right thing to do."
So the principal and his wife jumped in their car and got to work.
"She told me I was crazy," Montgomery said. "I tell you what, that first day, at the end of the first day it felt like I had made a mistake. Because it was hard," he said. He delivered a Snickers candy bar to each student and it came along with a dad joke.
He told them each that they'd look back on these days and "snicker." "I delivered that joke nearly 600 times. So it's pretty lame," he admitted.
"I just love our kids and they have awesome families I have found," he wrote on Facebook. "If I missed someone it was totally by chance."
It took 12 days and put over 800 miles on his car's odometer but Montgomery and his wife were able to reach all 612 seniors at trips to 636 addresses.
"I am now a well-traveled Wylie person and found parts of the town I did not know existed and so many Pirates that live on the other side of town was humorous as well," he wrote on Facebook.
The principal hopes that someday his school will be able to hold a graduation ceremony for the Class of 2020. Texas's statewide stay-at-home order ended on Thursday so people are starting to get back to normal.
Non-essential businesses, including shopping malls, retail establishments, movie theaters, are now allowed to operate at 25% capacity. Museums, libraries, and restaurants are now open as longs as people practice social distancing.
Large gatherings in the state are still forbidden until further notice.
Montgomery's trip surely brightened the days of his students on lockdown, but it meant just as much to him. "All I know is that for me it was something I needed to do," he said, "I can't adequately describe the reward it is to get to do this and see these kids in their natural environment."