His son, Hunter, has two favorite UK football players - Jared Lorenzen and Derek Abney. Montgomery came back to Boyle County with an Abney jersey for him and a football autographed by both players is on the way.
"We stay so busy, that we don't get to go to many football or basketball games or even any NASCAR races," Montgomery said. "Thank God for satellite on the tour bus. When it comes to UK, we will find a way to listen."
That's the price Montgomery Gentry pays for its huge national success. It's why fans from Louisville, Elizabethtown, Glasgow, Tennessee and Indiana were among those lined up here Sunday with cash and toy donations to see Montgomery and his two tour buses.
"We don't want any kid to go through Christmas without toys," he said.
Concert at Rupp Arena on New Year's Eve
Of course, Montgomery will be just like a kid at Christmas Dec. 31 when his group headlines a New Year's Eve concert at Rupp Arena where his beloved Wildcats play.
"That's going to be so great," he said. "That's where you have a lot of big concerts, but it is also the home of the Big Blue. I've gone to concerts and games there. I can't wait. It's going to be very emotional. We might start at 7:30 (p.m.) and end at 7:30 (a.m.)."
Montgomery Gentry has some well-known musical talent - Charlie Daniels, Phil Vassar and Dierks Bentley - joining them for the concert. But they might not be the only ones on stage.
"We are hoping to pull off a few surprises to make it one crazy night," Montgomery said.
Surprises? Maybe someone with Big Blue ties?
"I don't want to say because no one has officially committed yet," Montgomery said. "I do guarantee you I will wear my Kentucky jersey that night. Me and T (Troy) both will."
He also said they eventually want to have a song about their beloved Wildcats and that several writers have been working on songs about UK for them.
"We just have not quite got what we wanted. We hoped to have one for our next album and had one we thought might work. But you know when something is right, and it wasn't. It just has not come together yet, but it will. Count on that," Montgomery said.
He's also counting on Boyle and Danville to both win state titles this weekend. It would be a record-setting fifth straight for Boyle and 10th overall for Danville, which also won in 2000 and 2001.
Montgomery would like to be at both games. Instead, he'll be on a cruise with Montgomery Gentry fans that was scheduled by his promoters.
"If someone would put those games on satellite so I could watch, or even listen, I would pay for it," Montgomery said. "I've already called my cellular phone service to make sure I can make calls, or get calls, about the games. I want to know what is going on.
"What I want for Christmas is two more state titles for Title Town. I know this. Title Town is here to stay and I'm proud to be from Title Town. It just kills me I can't be at the game, but I'll be pulling for both teams. We've got something special here no one else has."
True, but the same thing could also be said about Montgomery. He's not let success change his roots, especially when it comes to his love for Kentucky sports and/or Boyle and Danville football.
Tickets are on sale
Tickets to the Montgomery Gentry concert, priced at $47.50 and $37.50, are on sale at the Rupp Arena ticket office or by calling 859-233-3535.