While attending Whitehall High School, Simmons led his high school team to three straight league titles, and also led the CoplayAmerican Legion team to two Pennsylvania state crowns. In 1947, Phillies owner Bob Carpenter arranged for an exhibition match between his Phillies and a team of all-star high school players from the Lehigh Valley. The game was played on the opening day of Egypt Memorial Park in front of a crowd of 4,500. Simmons struck out eleven and the game ended in a 4–4 tie. The, lefty was signed by the Phillies, and awarded a $65,000 signing bonus. That spring, Simmons also pitched and played outfield in an All-American high school game between teams managed by Babe Ruth and Ty Cobb. In 1949, Simmons returned to the Lehigh Valley, pitching for the Phillies in an exhibition match against the Allentown Redbirds, in front of a record crowd of 4,590 at Whitehall's Breadon Field. Simmons won 17 of 25 decisions during the 1950 season, playing a role in bringing Philadelphia its second National League championship of the 20th century. With the outbreak of the Korean War, however, Simmons was called to active military service in September 1950, with only a month remaining in the campaign. The Phillies managed to hold off the Brooklyn Dodgers in the 1950 season's final contest to win the NL flag by two games. Simmons was stationed at Camp Atterbury and requested and was granted a leave on October 4, 1950 to attend the Series. The Phillies chose not to request that the Commissioner of BaseballHappy Chandler rule Simmons eligible for the Series, but Simmons chose to attend to support the team. Simmons' place on the Series roster was taken by pitcher Jocko Thompson. Without Simmons, the Phillies were swept in four games by Joe DiMaggio and the New York Yankees. Simmons also missed the entire campaign while in the military, but he returned in to win 14 games and post a stellar 2.82 earned run average. The team would never again contend for a championship during his tenure there, although Simmons continued to pitch into the late 1950s. In, he was stricken with a sore arm, and in, the Phillies – now in last place and in rebuilding mode – released him on May 17, 1960, after four mound appearances. Signed as a free agent by the St. Louis Cardinals three days later, Simmons began a comeback that culminated in 15- and 18-game-winning seasons in –1964, while in a pitching rotation that included Bob Gibson and Ray Sadecki. In 1964, he appeared in the World Series against the Yankees. He started two games for the eventual world champion Cardinals, losing his only decision but compiling a 2.51 ERA. Simmons’ last winning record was in 1964; he lost 15 games for St. Louis in, then finished his career with the Chicago Cubs and California Angels, in –. His final record, over 20 years, was 193–182. In 569 games pitched and 3,348 innings, Simmons allowed 3,313 hits and 1,063 bases on balls. He recorded 1,697 strikeouts, 163 complete games, 36 shutouts, and five saves. Along with Smoky Burgess, Simmons was the last player to formally retire who had played in MLB in the 1940s. MLB Hall of Fame hitters Hank Aaron and Stan Musial each separately named Simmons as the toughest pitcher they had to face in their careers.
