Tom Foley — a fellow baseball lifer who helped build the Tampa Bay Rays from inception in the ’90s — remembers first encountering Charlie Montoyo. It was 1995 and a 35-year-old Foley was playing shortstop for the Lynx in the final season of his career. Montoyo was playing short for Scranton. “I saw this guy walking up to the plate choked up three inches and he hit a home run,” Foley remembers. “I’m watching this guy round the bases, like, ‘How the hell did he do that?’”

The following spring training, now working as a field coordinator and farm director for the nascent Rays, Foley visited with a bevy of MLB teams trying to learn how, exactly, a professional baseball organization is run. One day, while Foley was spending time with the Expos in West Palm, Florida, the guy who choked up three inches walked over to introduce himself. He said he knew his playing career was coming to an end but he wanted to stay in the game as a coach. He asked Foley if he’d keep him in mind as he was building out Tampa’s staff. “I definitely felt highly of him. For him to walk up and express that to me, and to have a really sincere conversation about his desire to stay in the game, that went a long way,” Foley says. “When I spoke to him, we didn’t have many coaches; we didn’t even have any players in the organization. So, why not give him a shot?”

At the Letters Ben Nicholson-Smith is Sportsnet’s baseball editor. Arden Zwelling is a senior writer. Together, they bring you the most in-depth Blue Jays podcast in the league, covering off all the latest news with opinion and analysis, as well as interviews with other insiders and team members.

Foley called that October, and the ensuing spring Montoyo’s managerial career began with the rookie ball Princeton Devil Rays. He earned a promotion to the short-season Hudson Valley Renegades a year later, and another to the single-A Charleston RiverDogs a year after that. Montoyo met his wife, Samantha, in Charleston, and she went with him as he continued to climb the Rays’ ranks, eventually arriving in double-A with the Montgomery Biscuits in 2004. In his third season managing Montgomery, Montoyo led the Biscuits to a 77-62 record and won his first championship. Justin Ruggiano, who went on to play nearly 500 games in the majors, was an outfielder on that team. “Charlie was super hard-working, super hard-nosed. He’d challenge you. He expected you to play a certain way,” Ruggiano says. “He’d jump your butt for not hustling a groundball. Even if it’s a groundball to the pitcher. If you dog it and disrespect the jersey, he’s pulling you out of the game right then and there. It could be the last week of the season, you’re exhausted — it didn’t matter. He always expected the same thing. I’m putting you in the lineup, you need to give me 100 per cent.”

He’s a calm, mild-mannered presence today. But this was a different Montoyo. Fiery and combative, he wouldn’t hesitate to chew out umpires, to dress down a player in the dugout, to tear a strip off his entire team in the clubhouse after a game. When he was ejected, he’d make it worth his while, sometimes needing to be physically restrained and shepherded back to the dugout. As a player, you did not want him to catch you slacking. Ruggiano says he can’t recall how many times Montoyo benched him — there were too many to count.

No one was spared. Criag Albernaz signed with the Rays that year as an undrafted catcher out of Eckerd College, an unheralded Div. II program. When one of Montgomery’s catchers was injured in a home plate collision, Albernaz was called all the way up from rookie ball right before the Biscuits playoff run. Raw and still learning how to call a professional game, Albernaz committed a slew of minor mistakes, the kind of subtle errors that go unnoticed by many fans but drive coaches nuts. Montoyo didn’t let him get away with any of them. “I could tell when I first walked in that clubhouse — it was Charlie’s team,” says Albernaz, who’s now a manager himself in the Rays organization. “Whatever happened on that field or in that clubhouse was what Charlie wanted. And all the players had the utmost respect for him. You could see that right away. Everyone bought in.”