That was just one of the laughs the teammates shared as they made their way to our nation's capital for All-Star Week, where Lester, Baez and Willson Contreras will represent the Cubs in the 89th All-Star Game presented by Mastercard on Tuesday night.
Also on the flight to Washington was Kyle Schwarber, who along with Baez, was part of Monday night's T-Mobile Home Run Derby.
Schwarber belted a Derby-best 55 homers and finished second to Bryce Harper, while Baez hit the event's longest homer at 479 feet and 16 total in a first-round loss to the Dodgers' Max Muncy.
Lester may be an All-Star for the fifth time, but Baez and Contreras are first-timers, while Schwarber was making his Derby debut.
"The biggest thing I told them is just be prepared for craziness," Lester said. "It's non-stop from when we get here until when we leave; that was probably the most eye-opening thing for me my first time. You have 10 minutes to sit down with your family. The big thing is to just have fun. Don't worry so much about the Home Run Derby or the game; just kind of sit back and try to enjoy it as best you can."
Lester won't pitch in the All-Star Game, having started for the Cubs on Sunday in San Diego. As honored as he is to be part of the festivities, the 34-year-old seemed more excited to see his teammates go through the experienced for the first time.
"The big thing for me is watching these two knuckleheads over here have fun," Lester said, pointing toward Baez, 25, and Contreras, 26. "I'm excited for them. Obviously, I'm excited to be here for myself, but I get to kick my feet up and watch these guys, so it will be fun."
Lester has shared an All-Star clubhouse with many teammates in the past, but being here with Contreras was especially meaningful to him. David Ross served as Lester's personal catcher during his first two seasons in Chicago, but once the veteran backstop called it a career after the 2016 World Series, Contreras and Lester began their working relationship.
"On a personal level, it's even more gratifying for myself," Lester said of Contreras' All-Star nod. "With the whole Rossy thing, I know that was kind of a chip on his shoulder. When Rossy retired, he wanted to be that guy -- and he has. He's done an extremely good job in every aspect of the game. I'm very proud of the way he's grown, both physically and maturity-wise behind home plate."
"If he says so," Contreras said with a grin. "Lester is an amazing teammate and an amazing pitcher. If he says that, I don't have to say anything else. ... Now that we've gotten to learn each other more, to know each other more, it's been way easier than before."
Baez will lead off and play second base for the National League, while Contreras will start behind the plate and hit ninth.
"Javy's athleticism just makes him above and beyond those guys; not only on the basepaths, but he plays multiple positions," Lester said. "If you're able to do that, that puts you in a pretty special category. Three years ago, we had him playing center field. He's a special talent. The game just seems so slow and easy to him."
When Baez learned he had been voted as the NL's starting second baseman, he began laughing. Contreras, on the other hand, had a different reaction.
"He started crying," Baez said. "I said, 'Are you happy or are you not happy?"
The emotion Contreras felt carried into Monday as Contreras talked about the feeling of sharing a room with the best players in the world.
"It means a lot; it means another dream came true," Contreras said. "First there was the World Series in 2016, now an All-Star; it's something I dreamed about since I was a kid. I used to tell my mom and dad that I wanted to be in the big leagues, but also that I wanted to be an All-Star. Now I'm here, so I'm trying to enjoy every single second of this."
Lester knows the feeling. He remembers being a first-time All-Star in 2010, his fifth season with the Red Sox. For the lefty, it was a sign that he had taken his game to the next level, much the same as Baez and Contreras have in the early years of their respective careers.
"When I got to my first All-Star Game, it just kind of makes you feel like you belong; like, 'I am pretty good,'" Lester said. "To get rewarded for your hard work, to get to be able to do this, it's like that little pat on the back or 'Good job.' Hopefully they see that and hopefully they feel like they are two of the best in the game and that just carries over to their game."
Mark Feinsand, an executive reporter, originally joined MLB.com as a reporter in 2001.