After graduating from Morris High School in The Bronx, he worked in several jobs while developing a deep interest in baseball history, rules, and statistics.

By the 1930s, he was spending a lot of his free time in the New York Public Library researching old newspapers about the early accounts of matches.

At that time, he developed a friendship with Ernest Lanigan, a baseball historian and Information Director of the International League.

From 1940 to 1942, Simmons selected the top baseball performer of the day for the popular radio show "Fred Waring and his Pennsylvanians."

He contributed original work to the top baseball writers of the day: J. G. Taylor Spink, Leonard Gettlson, Hy Turkin, S. C. Thompson, and Lee Allen.

In 1965, he appeared in the CBS television show To Tell The Truth and managed to receive no votes when asked, "Will the real Mr. Simmons please stand up".

He started to compile some of these odd plays which the umpires would ask him about, and in 1949, he submitted "a pack of these nutcrackers" to The Saturday Evening Post under the title "So You Think You Know Baseball".

Over the years, Simmons gained more International League responsibilities in handling player trades, dealing with the press, scheduling the games, the hiring, firing and movement of the umpires, settling disputes among the clubs, handling the financial side of league operations, and staffing the office.

[7] Simmons quickly became a popular figure in Montreal baseball circles and gave many speeches to local community groups.

In March 1953, when the Boston Braves moved to Milwaukee, National League president Warren Giles called on Simmons for some quick schedule changes.

After the 1960 season, when the Montreal Royals folded (becoming the Syracuse Chiefs) and Shaughnessy retired, the league offices were moved back to New York City.

[9] Simmons received consideration to succeed Shaughnessy, but the position went to Tommy Richardson, then president of the Eastern League.

He directed Gerry Snyder of the mayor's office on how to go about getting the franchise and recommended the hiring of Jim Fanning and John McHale to run the club.

[16] In the more than 50 years that he was involved in baseball, Simmons collected thousands of items related to the development of the game from its earliest times.