The team featured four Hall of Fame players, including "Mister Cub" Ernie Banks. It was his best chance to make it to the post season.
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Author Ron Rapoport said not making it to the World Series would haunt Banks for the rest of his life.
"He never had his World Series moment, he never had that basket catch, he never did what Hank Aaron did, break Babe Ruth's record," Rapoport said.
"I mean, he was this unicorn, he was doing something different, he was playing a different game," he continued. "In those six seasons when Ernie was this great hitter, the Cubs finished a combined 123 games out of first place."
That was the relentless fate of Mr. Cub; a gifted athlete, ever beloved by the fans of a team that couldn't win.
"He would go to Cooperstown. He'd look around the room and he'd see he was the only one there who'd never played in a World Series," Rapoport said. "It hurt him terribly, again, he tried to hide it behind a smile."
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Banks didn't like conflict on or off the field.
"When things were heating up in the 60's, when the Civil Rights movement was heating up, Hank called Ernie and he called Willie Mays, he said you guys have to speak out things are changing, we can control some of the dialogue, Willie and Ernie wouldn't do it, Ernie just would not do it and he took a lot of heat," said Rapoport.
Mr. Cub died 18 months before the Cubs broke the curse and won the big one. He's buried just north of Wrigley Field.
"People were not only going to Graceland Cemetery as they were starting to play the World Series to lay flowers on his grave and maybe pray to the baseball gods by Ernie's grave, they were also going to the cemetery for their fathers and their mothers who'd watched the games, black and white because they never got to see the Cubs in the World Series," Rapoport said.