But as difficult as this day is for him each year, Whidby hasn't let his tragic memory remove his ability to love others during the holiday.
The 33-year-old describes himself as "like a book." This is probably because he opens himself up so generously to others.
"Whatever I got, I like to give," he said. "I've been known to go to Kroger and buy a gift card for someone laid off."
So it was only natural for him to think, "What can I do at home?" when he learned about the international, volunteer-led nonprofit organization Soldiers' Angels while watching the news.
The organization, founded by the mothers of two American soldiers, supports America's men and women in uniform with more than 30 different teams and projects and nearly 200,000 volunteers.
Whidby wanted to help boost the morale of those fighting for the country and those who have loved ones in the war, whom he can relate to. His mother's first cousin fights in Afghanistan and has returned home on holiday leave.
But not all soldiers get that opportunity. So he planned to send a box of "little things (the soldiers) can't get over there" just in time for Christmas.
After receiving blessings from his pastor, the Rev. Gavin Moon of Voice of Pentecost Church on Salem Road, Whidby, with the help of his mother, began his own Soldiers' Angel ministry.
However, beginning something so influential came with its obstacles, something Whidby is familiar with having grown up legally blind.
It took two weeks just to gather the contact information he needed and a total of two months to get all he needed to reach the point of collecting items for the package.
"You got to do what you can do to get by," he said. "When people say, ‘Don't (or) can't,' ... I just say, ‘Watch me!'"
Whidby stayed determined. Church and community members reached out with monetary donations to add to his own contribution. And last week, Whidby and his mother purchased 41 pounds of items, including candy, coffee, mugs, creamer, wipes, sanitizer, jerky, razors, dark clothing, little Bibles, from the Dollar Store for soldiers to receive Christmas morning.
"We tried to send a little bit of everything," said his mother, Georgia Ann Whidby.
Now that he's successfully sent off a package for Christmas, Whidby hopes to be able to send packages every major holiday. His goals for his ministry are for it to grow and for more people to do more and help out.
According to his mother, Whidby wants to start earlier next year and send more.
"It doesn't take much," he said about making a difference on a limited or fixed income. "People can afford 50 cents to go to the Dollar Store. You don't have to have much to tell someone you're proud. Just a kind word - do anything to keep morale up."
To do your part in keeping morale up, send cards to: A Recovering American Soldier, c/o Walter Reed Army Medical Center, 6900 Georgia Avenue N.W., Washington, D.C., 20307-5001. Monetary donations can be sent to: Soldiers' Angels, 1792 E. Washington Blvd., Pasedena, CA, 91104.