"Everybody just assumes that people within these circumstances or conditions are people who don't want to work, or they're lazy, or whatever," Maddon said. "There are a lot of different reasons why people end up in that situation. And this economy is showing it right now, front and center.
"There are a lot of folks out there who would really much prefer having their steady job back and their homes, etc. This is a tough time. When you're considering the homeless situation, it's a wide variety of people and a wide variety of reasons why they're there."
This year is Maddon's third consecutive year hosting the event. As he has done in the past, Maddon prepared a traditional Italian holiday feast Tuesday night as he will at the events that follow for the remainder of the week.
With the help of Rays employees, Maddon shopped for the food on Sunday before helping to cook and serve it Tuesday night. The Rays provided gift packs for the youngsters and Wal-Mart donated gift cards to those receiving meals.
"I've been wanting to just grow this thing to the point where we include families and kids, because people don't even consider the children involved in this situation," Maddon said. "It's always about a male. It's normally a male, 40-plus, or whatever, but it's families.
"So the more we get the information out there, and the more we shed light on the situation, the more people gain an understanding. And I need to be more educated on it myself. But I do know one thing -- it's one of those things that sticks to me and I felt like I needed to do something about it."
Keeping the kids in mind, Maddon wanted to add toys to the events this year.
"Last year, when we went to the Metropolitan Ministries and at Bradenton, it was the first time we were exposed to families and single moms," Maddon said. "And, my goodness, it's tough, because you know where you came from, you know where you grew up. And you know what you've got right now and you see what you've got. And for me, it's a tough thought."
Maddon doesn't hide the fact he annually gets moved to tears when hosting the events.
"When I get over my crying, in a quiet corner somewhere, it's great," Maddon said. "The kids are appreciative. The parents, the people are very appreciative. And also the people that work in these places. We've really built a pretty good relationship with them also. And furthermore, it's Christmas, man -- it is the best day of the year."
"Thanks-mas" will include the following stops the remainder of the week:
Wednesday at 5:30 p.m. ET at Tampa Salvation Army, 1603 N. Florida Ave.; Thursday at noon at Port Charlotte Salvation Army, 2120 Loveland Blvd.; and Thursday at 5 p.m. at St. Petersburg Salvation Army, 1400 4th Street South.
Bill Chastain is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.