CLEVELAND -- Mike Montgomery was making his way through the parking lot toward the Chicago Cubs' spring training clubhouse when he noticed a station wagon parked near the entrance. Inside, Joe Maddon was fiddling with his car's sound system and yelled out, "Hey, come check this out," so the reliever hopped in the passenger's seat of his manager's car.
"There was something wrong with the Bluetooth," Montgomery recalled. "So I got in the car, and he started telling me about this vintage station wagon [1985 Oldsmobile Custom Cruiser], and we started talking cars. We had a great conversation. You don't really get that with a lot of managers, and he certainly didn't seem like the oldest manager in the game at that moment."
The interaction came during a casual break from the grind of spring training in Mesa, Arizona, but it could have just as easily happened around the batting cage during a road trip or even in the dugout between innings, as sometimes the conversations take place in-game -- yet have nothing to do with baseball. Managers connecting with their players is nothing new, but the older a manager gets, the tougher the task becomes.
That doesn't seem to be the case for the Cubs' 64-year-old skipper, who became the oldest full-time manager in the game after Dusty Baker was fired and Terry Collins retired at the end of last season (Reds interim manager Jim Riggleman, who took over in Cincinnati for the time being last week is 65). Maddon has no intention of stepping away any time soon -- as long as the Cubs or another team want him, of course. So how does he do it? How does a man entering retirement age stay relevant in a job that depends on relating to athletes in their 20s and 30s?
Perhaps the most important element in answering that question came in the fact that none of his players -- not one -- realized the Cubs have the oldest manager in the game.
"He's unbelievable," pitcher Kyle Hendricks said. "He connects with everyone, no matter how young or old. That's just one of his qualities. He finds common ground. He's a big relationship kind of guy. And it pays off. I would never have known he's the oldest manager in the game. It's not something you notice."
Hendricks says he'll talk with Maddon about life between innings. Just small talk, but it resonates because the manager is making the effort.
"He may be the oldest manager in the game, but it doesn't really feel that way," Cubs newcomer Steve Cishek said. "He's new-school. That separates him from a lot of the other older guys."
Does this mean Maddon is listening to Cardi B on his way to the ballpark? Not exactly, but there are different ways to connect, and Chicago's manager is a master of finding them. Being employable at an older age is something Maddon has put thought into, and he firmly believes the onus isn't on the employer, but rather the employee.
"I've had many coaches that I've worked with that have found themselves out of a job," Maddon said. "And almost every one of them refused to attempt to understand what was going on at the moment in the game. Whether you agree or disagree with how front offices are built or what they consider important, it doesn't matter. That's the way it is.
"When you fight that, you eventually deem yourself unemployable, I believe. Adhere to what you believe in. I do. But also, be open to what's happening right now. And in the future. If you morph those together, that's the balance everyone should be looking for."
As the game gets younger -- both on the field and in the front office -- the ability to morph is more required than ever. But it doesn't come hard for Maddon, who says that his natural state of mind keeps him relevant with what's going on.
"I feel like I've always remained contemporary, not by plan, but I've always been curious," Maddon said. "We are all raised in different generations. And whatever generation you come from, you're always going to have an old-school method to it. You know, from when you grew up. But in referencing the past, you have to stay current with what's going on now -- or even what's occurring down the road."
As the game evolves and the age of front-office decision-makers skews younger and younger, there's a strong possibility that we won't see another 72-year-old skipper lifting a World Series trophy, as Jack McKeon did with the Marlins in 2003. Maddon would like to make it to about 70 before calling it a career. McKeon is rooting for it but isn't sure it can happen.
"They're all young guys and all looked like they just came out of high school," McKeon, 87, said by phone. "When I was with the Marlins, you had guys that were interns. Next thing you know they're scouts. C'mon. The poor guy that's 65 years old, they want to push him out of the game because he’s too old. ... Of course I root for those guys. And I root for the young guys, but they forget about the experience that it takes."
Maddon's mindset has always been about combining the new ways of doing things with the knowledge that is gained only from experience. Before Tuesday's game against the Cleveland Indians, he expressed how grateful he was to have worked his way up the ranks to a managerial job, giving him a full understanding of a player's mindset in the big leagues. The result of all those years around players is a man who can relate to any of them.
Shortstop Addison Russell is a good example of someone who has benefited. Called up from the minors at age 21, Russell has been under the spotlight for a variety of reasons, and Maddon has been there for him in a way that goes beyond baseball. Russell has needed a settling influence at times.
"We talk family," Russell said. "But we talk Netflix, food, drinks and especially restaurants. He finds those common interests."
Do they watch the same Netflix shows?
"Sometimes," Russell answered with a smile that probably meant "not really."
McKeon stressed that dealing with baseball is such a small part of leading players. There is so much more going on behind the scenes.
"You're managing their whole life, helping them become better citizens," he said. "That's the fun part of it. You see guys take your advice and go on and do good things. Sometimes they don't. You just try and do your best with them."
Perhaps Maddon can continue to relate because he has never been by the book. He should be old and crusty, yet he remembers being annoyed by that very same trait when he was young.
"My first player evaluation meeting [as a coach] was in the Francisco Grande hotel [in Arizona] in the middle of spring training," Maddon recalled. "I'm sitting in this room with all the managers that are managing in the minor leagues, and they had all the power to decide the fate of these players. There was no overarching plan for any of these guys. It was about what they thought. It wasn't the GM, it wasn't a scouting director or farm director. It was just managers. You're totally at the whim of their prejudices, personally or as a player. I was appalled by what I heard in those meetings. It's almost 40 years later, and still I'm talking about [it]. I thought, 'If I ever had this opportunity, it's definitely not going to be that way.' I got to see what I would never do."
Maddon knows enough to stay out of the way of star players who don't exactly need baseball advice, too. Kris Bryant couldn't recall the last true baseball conversation he had with his manager.
"We talk about travel," Bryant said. "He tells me all these places I should go and try out. When I do talk to him, it's not baseball-oriented. We have a good grasp on the game, and he trusts us."
Count Bryant among the players who were surprised to find out Maddon was the oldest manager in baseball.
"That's crazy, he's the oldest?" Bryant asked rhetorically. "Everyone thinks of him as a new-age manager, and with that comes the conception that you're young, I guess."
Added Cishek: "What makes him unique is he's just approachable. I can go right up to him, and he'll talk away. A lot of other managers are so focused on the task. He just wants to be personable."
If there is one word that could describe Maddon's overarching philosophy, it's "balance." Finding it in his personal life has helped him in his work life.
"I have other interests," Maddon said. "That's what gives you the fire to do this. I talk about liberal arts constantly. I don't like specialization. The candle does burn out.
"I don't want an extreme old method. I don't want an extreme new method. I want to take them both. The advantage I have in this game is I work with young people all the time. That may have forced me, unknowingly, to follow this path, but if you're not around young people all the time, be careful. You need to understand what's going on with this new generation and the next one coming after that, if in fact you want to remain employable and be a benefit."
Maddon is signed through 2019, and conversations with the Cubs about an extension should commence in short order, as no one wants a lame-duck- manager situation next season. If staying contemporary is part of the job description, Maddon says he thinks he has that part down.
"When it comes to the future, I have to take care of myself physically and mentally to be able to be employable five to six years from now," he said. "That's not impossible the way I feel right now. Hopefully, with the proper guidance from above, if I do the right things, I have a shot at it -- if someone wants me."