The former Daytona 500 winner, in town this weekend for Nationwide Series and Sprint Cup races, found there was plenty of NASCAR love emanating from the room.
Mark Buehrle, John Danks, Jake Peavy, Adam Dunn and A.J. Pierzynski crowded around Waltrip and his crew, along with drivers David Reutimann, Martin Truex Jr. and Ryan Truex. Reutimann won last year's Sprint Cup race in Chicago, one of two he has won on the circuit.
"I love baseball," Waltrip said. "Just getting to peek inside the game, I feel really honored to be here just to see [it]. You watch a game on TV and you don't really think about all the things that go into it or what's behind the preparation. These guys have just been really nice to me, they make me feel like I'm part of the team. I really enjoy seeing this."
All four drivers suited up in full White Sox uniforms before taking the field to work out with the club. For Waltrip, it was the first time since Little League he has donned baseball gear, a memory he had been trying to forget.
"Little League didn't go well for me," Waltrip said. "We had the best team and I played third base, and everyone in the infield made the All-Star team but me. I determined at a very young age that it was probably going to be important for me to make a living sitting on my [rear end]."
Waltrip, a Braves fan, said he was pleased to meet a jovial Ozzie Guillen, even if the manager asked him why his locker was in "Latin Corner" and why he wasn't suiting up "with the rednecks." Buehrle, Danks, Peavy and Dunn affectionately call their line of lockers "Redneck Row."
"I loved his energy, you know? Saturday morning, spring training ... he bops in here like we're getting ready to play Game 7 of the World Series," Waltrip said. "That was fun seeing Ozzie and his energy. It's pretty obvious why people love playing for him."
Before he took the field, Waltrip was ready to add the day to his memorable sporting moments.
"I did play Augusta once," he said. "I've played crappy golf at a bunch of nice courses. Now I'm fixing to bring that same level to the baseball field. I'm happy about all this. This is fun."
Buehrle and Peavy were on hand for Friday night's truck race, making it the first NASCAR event Buehrle has ever attended. Buehrle, Danks, Dunn, Pierzynski and Gordon Beckham were scheduled to attend Saturday night's Craftsman Series race, sitting along pit row with Waltrip's crew.
Peavy, who is friends with NASCAR driver Jimmie Johnson, is expected to attend Sunday's Sprint Cup race.
Doug Padilla covers the White Sox for ESPNChicago.com.