Their combined credentials include 6,562 wins, 30 playoff appearances, 24 division titles, 10 league pennants and five World Series titles. And their careers all were intertwined with each other and with the Hall of Famer Berra, who hosted the event along with his wife, Carmen. Mattingly, for example, played for both Berra and Showalter on the Yankees and said he took a lot from Showalter's tenure.
"I liked that you could change the locker room mentality, and I thought that was so important to your success, when your club played hard, played with an attitude," said Mattingly, who was named the runner-up for the National League Manager of the Year Award earlier this week.
Some of the most intense discussion came in regards to analytics and how they interact with the human side of the game. All five managers expressed at least some appreciation for data, but also a healthy dose of caution about how they apply it.
Showalter talked about the danger of players thinking that decisions are coming not from the manager, but from the numbers. Mattingly expressed his belief that numbers can't sum up the power of a team working together. Leyland critiqued the wins above replacement (WAR) stat and insisted that not everything in baseball can be quantified. Girardi, who has an industrial engineering degree from Northwestern, summed up the collective viewpoint.
"I personally love numbers. That's my background," he said. "I love math, but I think you use the math to back up what you see, and I think at times, they use the numbers to try to prove a point.
"But it does support sometimes what you're trying to do. But the one thing it doesn't do, it doesn't tell you about a guy's heart. And that's what you need to know to know if he's going to be successful in the long run, and if you want him in the trenches with you when the game gets tough."
La Russa, who now works in the Commissioner's Office, didn't pull any punches in conveying his dislike for the popular book and movie "Moneyball," as well as its subject, one of his former players, Athletics general manager Billy Beane.
"[Michael] Lewis wrote a nice story, it's got some truth to it, and Billy has taken that thing and made himself a fortune and I'm very upset about it," La Russa said.
Mostly, La Russa is upset at what he sees as a trend of teams relying on analytics to the point of dictating lineups and strategy to managers throughout their organizations.
"It's an arrogance for these people to stand there and tell guys in baseball that this is how you should run the game," said La Russa, who retired after winning the World Series with the Cardinals in 2011. "It's arrogant and it's foolish, and if I managed again, I'd love to have five teams in the division using that process, and we'd clean their clock every day."
The panel also was asked about the challenge of dealing with players' insecurities.
Showalter discussed the importance of finding a guy's "button" that can be pushed in order to motivate him. La Russa talked about a "half-full" coaching philosophy that requires the manager to "show belief" in struggling players. Leyland, meanwhile, boiled down the job into simple terms.
"I've always felt like the manager needs to be there when the player's not going good," he said. "When everything's running smoothly and the player's playing good, they don't really need the manager."
The skippers also shared some of the biggest lessons they learned after stepping into their first job. For Showalter, it was about dealing with players, even good ones, who lacked confidence. For Mattingly, it was the responsibility of making so many little decisions throughout a game, as well as working with a front office. For Girardi, it was dealing with the New York media in a world of social media and 24/7 news cycles.
Finally, the subject of instant replay arose, with La Russa expressing his confidence that owners will approve the expanded system he helped formulate. While admitting there could be some hiccups in the first season, La Russa also believes it ultimately will speed up games and, most importantly, get more calls correct.