In '95, fiction became fact, right before his eyes.
"He was looking at all these people in Indians stuff," Sister Assumpta recalled. "He said, 'It's just like the movie!' And I said, 'No, Chris. The reason the movie was so successful was because it was like what it would be when we got there. You were envisioning the reality.'"
Though Cleveland went on to experience playoff glory in nonfiction form, the "Major League" movie still resonates with fans here. That's why, in commemoration of the re-release of the DVD version of the film, the club had a promotional Rick "Wild Thing" Vaughn glasses giveaway during last week's Rangers series.
By now, most fans know that the originally scheduled night for the promotion was April 10. But a spring snowstorm forced the Tribe to move that game to the indoor comforts of Milwaukee -- the very city where the baseball scenes of "Major League" were filmed.
Sitting in the stands at Jacobs Field last week, while he was in town to assist Sister Assumpta in the launch of her "Nun Better" cookie company, Chesser was asked why Milwaukee County Stadium was chosen over Cleveland Municipal.
Obviously, it's a question he gets quite a bit when he's in these parts.
"It was a real simple reason," he said. "We had a lot of conflict with the Indians' schedule, with both the Indians playing there and the start of football season. Some actors were only available on certain days. The Milwaukee park was designed by the same architect. It was a smaller version of Municipal Stadium, so it was easier to shoot in because of the size."
That's not to say Cleveland didn't get its due in the filming of the flick. Exterior shots were filmed throughout the city.
And one of those shots, as fans of the movie will quickly remember, is of Sister Assumpta herself. She's shown feeding a flock of pigeons outside the Old Stone Church on Public Square, while wearing her trademark Indians jacket over her habit.
It was a small role, but one that Sister Assumpta still gets noticed for, especially as the movie gets played incessantly on cable TV.
"I'll be shopping at Giant Eagle," she said, "and someone will say, 'I saw you in the movie last night.'"
Ever since she was spotted at Municipal Stadium in her Tribe jacket and was picked to appear in the picture, Sister Asssumpta and Chesser have been good friends. They sat together in the club seats at The Jake for last Thursday's win over the Rangers and reflected on the 18-year-old film that brought the Indians to the big screen.
So, why were the Indians chosen for the movie?
"[Director] David [Ward] was the driving force behind the Cleveland part of it," Chesser said. "We developed it together five years before and couldn't get it made. The reason we picked the teams was he was a big Cleveland fan, and I was a big Yankees fan, but I grew up in Tucson, a block and a half from Hi Corbett Field [where the Indians used to train]. The only professional baseball I saw as a kid was the Indians against somebody else."
Once Ward and Chesser had a script completed, they had to get approval from the Indians. That's where former media relations director and current vice president of public relations Bob DiBiasio was brought into the fold.
"[General manager] Hank Peters had a stack of papers on his desk," DiBiasio remembered. "He threw them at me and said, 'You're in charge.'"
DiBiasio didn't change anything, except for one Rocky Colavito reference that didn't sit well with him.
When the movie premiered in Cleveland in April of 1989, DiBiasio sat in the crowd, behind Peters and his wife, Dottie, who wasn't exactly a fan of the multitude of F-bombs peppered throughout the film.
"The movie's over, and Dottie Peters stands up, turns to me and says, 'You had script approval of this?'" DiBiasio recalled. "I happily said, 'Yeah.' And she said, 'Do you kiss your mother with that mouth?'"
Sister Assumpta, as you might imagine, was no supporter of the swearing, either. But she still has a soft spot in her heart for much of the movie's dialogue.
"I have the lines memorized," she said. "Whenever I'm having a bad day and just need something, I put that on and laugh."
She's not the only one. "Major League" has, after all, been ranked highly in countless "Best Of" lists for baseball movies, and its impact is still apparent, be it through Charlie Sheen and Bob Uecker reprising their characters for a new DirecTV commercial, the DVD release or the many one-liners that sneak into sports highlight shows.
"In a lot of ways, it's more popular now than it was before," Chesser said. "Before, it was just a baseball picture. Now, on "SportsCenter," every time you see a wild pitch, somebody goes, 'Juuuust a bit outside!' There are certain things from the picture that have become iconic things."
But what matters most to Chesser is the reaction Indians fans have had to the movie that put their beloved Tribe in the limelight.
"People will come up and say, 'I love that movie,'" Chesser said. "And you know they mean it because they'll quote some lines that you don't even remember yourself."