Swimming in a sea of Yankees hats, the boy was struck by the Cardinals blue cap with the red "StL" stitched in front.
Rather than go with the flow and choose the Yankees hat, Maddon went counterculture in the Bronx. He left the historic ballpark that night wearing a Cardinals hat, and he's been a Cardinals fan ever since -- an allegiance that extended to the NFL's Cardinals (formerly of St. Louis) as well. Upon request, he can rattle off lineups from the old baseball or football Cardinals.
Maddon has never been one to follow.
In 2006, Tampa Bay hired Maddon to be the manager of a struggling franchise, the Devil Rays. After two seasons at the helm, his record stood at 127-197. Could the new ownership group headed by Stuart Sternberg have made a grave error in its managerial choice?
Prior to the 2008 season, the Devil Rays became the Rays, even going so far as to change out the team's green uniforms to coincide with the change. Nothing changed with Maddon that season, save for his team's record, as the Rays posted a 97-65 mark en route to the organization's first and only World Series appearance.
Maddon has always strived to make the Rays' clubhouse a place where players want to be. At times, he's gone to great lengths to accomplish that mission.
Following that sentiment, he instituted themed road trips in which the team dressed according to the theme. For example, the Rays' road trip to the West Coast had a college-football theme in which everyone wore the jerseys of their favorite team. There have been countless others, some of which caused players to roll their eyes. But corny or not, it worked.
"Some of it seemed silly at the time, but once you leave, you realize that's the kind of stuff that helps a team win and bring them closer and all that other stuff," former Rays outfielder Carl Crawford said. "What might look silly to other people is actually what's good for those guys."
Theme trips aside, Maddon elevated the fun in the clubhouse this season where, on any given night before the game, a DJ, a cockatoo, a magician, penguins, or even a python could be found.
Recently, Maddon has been on a jag about his new RV, a 2014 40-foot Tiffin Phaeton, which retails for approximately $300,000. Despite the constant teasing he receives, he has remained adamant about his plans to live in the RV during Spring Training in Port Charlotte, Fla., next year -- unless he upgrades to something bigger.
Delmon Young is in his second tour of duty with the Rays, so he experienced Maddon's tutelage in the early days of the manager's tenure and offered his perspective on how Maddon has changed.
"Eight years [into his tenure as manager], everything's been kind of established for him, where he doesn't have to come in and say a whole lot," Young said. "When he got here, he went into a situation where it was an organization, and a team, that had never won before and he had to change its identity -- and that happened. Now, this is a place where a lot of players want to come to and play.
"Now, it's understood from all the players and the rest of the staff what goes on here -- it's a good thing. So he doesn't have to come in here and set the rules for what we have to do. Guys come in, and when the game starts, everyone's out on the bench ready to play, supporting their teammates."
Young noted that in addition to playing for Maddon, he has played for highly regarded managers Jim Leyland and Charlie Manuel.
"They all go by their own style," Young said, "and the front office does a good job of letting them manage the team."
Fernando Rodney has been one of the Rays' all-time best reclamation projects. The Rays signed the right-hander prior to the 2012 season, after Rodney put together a dismal season for the Angels in 2011. Rodney became the Rays' closer and enjoyed perhaps the best season accomplished by a closer in history, logging a 0.60 ERA in 76 appearances, with 48 saves. A part of that success could be credited to the way Maddon handled the Dominican Republic native, building up his confidence whenever possible.
"What I heard about this guy before I came here, [Joel] Peralta told me, [Joaquin] Benoit told me, [Rafael] Soriano, that he's a good guy, good manager," Rodney said. "He wants you to go get comfortable before you go out there. He says that's most important for the ballclub."
A part of feeling comfortable is creating a fun environment. Rodney called the current Rays clubhouse the "most fun" clubhouse he has experienced. He allowed that having the fun environment really can really help a player when he's struggling, as Rodney was earlier this season.
"He knows how it is as a player," Rodney said. "He knows how to talk when you're going through a tough situation, like me this year when I struggled. He told me, 'Calm down; you know your stuff is there. So someday, it will be better.'"
Maddon enjoys relating to people and seems to particularly enjoy communicating with his Latino players by speaking Spanish with them the best he can. He is continually trying to better learn the language, which Rodney said is appreciated by the team's Latin players.
"It's hard for him to speak a different language," Rodney said. "You can see in his face he tries every time he comes to talk to you, he tries to say something in Espanol. And then he speaks in English."
Rodney smiled when asked if Maddon's Spanish is improving.
"Yes, it is better," Rodney said. "Getting very good. He speaks it very good."
Maddon has dared to be different. And that has worked.