In 1946, Mr. William Ahern Sr. established the Peppers as a South Side neighborhood team. They were a powerhouse from the beginning, winning money and beer games that were prevalent at the time. In 1965, William Ahern Jr. (Bill), the oldest son of the founder, took over the reins of the team and began to build their reputation for high-caliber play. They played two nights a week at Carrol Park (now known as Hayes Park).

In 1971, the team’s reins were passed on to George Ahern, the youngest son of William Ahern Sr. He took the team from a neighborhood powerhouse to a top level “A” and Major softball team that competed at the top levels of sixteen-inch softball. In 2000, Mike Ahern, son of George, stepped up to run the team at Mt. Greenwood Park. The team still plays today on Monday and Wednesday nights, for an unprecedented runoff of sixty-seven years and counting.

Over the years, the Peppers enjoyed phenomenal success at the local and park district levels, winning numerous league championships. They also competed
in the highest levels of softball and, despite never winning a national title, were always know as a team that would compete until the final out. These were the parks that the Peppers played at from 1965-1999: Carrol (now Hayes), Bogan, Rainey, Hancock, Currie, Bedford, Mt. Greenwood, Westlawn, Nowmandy, Pasture, Blue Island Park District, Oak Lawn Park District and Burbank Park District. They won championships at all but Blue Island and Pasture Park.

The Peppers played in national tournaments in Marshalltown, Iowa, Mt. Prospect, IL., Aberdeen, S.D., LaPorte, Indiana and Des Moines, Iowa. They played yearly tournaments at Cedar Rapids, Iowa, and Lacrosse, Wisconsin.