In the 1945 World Series against Detroit, he played three games and went 0 for 2. The Cubs lost in seven games and haven't made it back to the Series since.
However, the perennially scrappy Cubbies imagined they'd make it back soon enough, Merullo recalled recently.
"Yeah, sure," he said. "We never gave up hope."
Merullo's death Saturday was announced by Cubs owner Tom Ricketts.
The Cubs' oldest alumnus, Merullo traveled from his home in Reading, Mass. last year to a 100th anniversary celebration of the Cubs' Wrigley Field. He was 97 at the time — just three years younger than the stadium.
Wearing a Cubs jersey, he used a walker to get from his wheelchair toward the mound and threw out the first ball before the Cubs played the Marlins, getting a big cheer from the fans.
During the seventh-inning stretch, the former shortstop was center stage for another ballpark tradition. Belting out "Take Me Out to the Ball Game" over the stadium's sound system, he drew another ovation.
Born in East Boston, Mass. on May 5, 1917, Merullo, one of 12 children, played ball in the neighborhood before becoming a high school standout. He played for Villanova University before signing on with the Cubs.
Merullo made his Chicago debut in 1941 and played until 1947. He had a career batting average of .240 and hit six home runs.
On Sept. 13, 1942, he set a Major League record by making four errors in one inning — all on back-to-back plays.
He later explained that he was off his game because of excitement; he had just received news that his wife had gone into labor back in Boston.
His oldest son Len was nicknamed "Boots" because of his dad's bad night on the field. Boots Merullo went on to play minor league ball. Lennie's grandson Matt Merullo spent six years in the majors, mostly for the Chicago White Sox.
Merullo married next-door neighbor Jean Czametzki in 1941. They had been what a friend called "window lovers," Merullo told the Boston Globe in 2010.
"I'd be looking out my window to see if I could see her," he said. "And if she saw me, she'd look out her window. On foggy days, we'd draw S's in the window for 'Sweethearts.'"
Merullo's survivors include his wife, four sons, and a number of grandchildren and great-grandchildren.
After his playing career, Merullo spent decades as a scout for the Cubs.
He also became a kind of running gag in annual Cubs quizzes posed by Chicago columnist Mike Royko.
In 1989, Merullo responded with a heartfelt protest, which Royko featured in a column.
"Mike, I never professed to have been a good Major League shortstop with the Cubs," Merullo wrote. "As you have put it, I was a no-hit, very erratic player. I've had to live with that.
"However, it was not from not working at it. I worked at it too hard. I was not relaxed. Too tense.... Perhaps my contribution to baseball can be described as being able to understand and have a feel for the player who is having a bad day, as I have had many."
Contrite, Royko promised to quit making Lennie Merullo jokes. He even scrapped his customary question about the errors, replacing it with one about a memorable brawl between the Cubs and the Brooklyn Dodgers.
"Name the Cub player who separated Dixie Walker from his front teeth," the new question went.
Royko's answer: "The immortal Lennie Merullo, of course. So don't tell me you never gave us anything to cheer about, pal."