Phil Cavarretta's journey in Major League Baseball began when he joined the Chicago Cubs as a teenager. Born in Chicago, Illinois, Cavarretta was a local talent who quickly caught the attention of the Cubs' scouts. He made his debut with the team at the age of 18, stepping onto the field as a first baseman and outfielder. His early years with the Cubs were marked by steady development as he honed his skills and adapted to the demands of the major leagues.

Cavarretta's left-handed batting and fielding abilities soon became assets for the Cubs. Over the years, he established himself as a reliable hitter, consistently maintaining a solid batting average. His breakout season came in 1945 when he played a crucial role in leading the Cubs to the National League pennant. That year, Cavarretta achieved a career-high batting average of .355, earning him the National League Most Valuable Player (MVP) award. His performance was instrumental in the Cubs' success, and he also excelled in the World Series, although the team ultimately fell to the Detroit Tigers.

Throughout his tenure with the Cubs, Cavarretta was known for his consistency at the plate and his defensive skills. He was selected to the All-Star team multiple times, reflecting his standing among the league's top players. His leadership qualities were recognized when he was named player-manager of the Cubs in 1951, a role he held for two seasons. However, managing proved challenging, and he eventually returned to focusing solely on playing.

In 1954, Cavarretta's long association with the Cubs came to an end when he joined the Chicago White Sox. Although his time with the White Sox was brief, he continued to contribute as a player before retiring from Major League Baseball. Over his career, Cavarretta accumulated more than 1,900 hits and maintained a batting average of .293, reflecting his consistent performance over two decades.

After retiring as a player, Cavarretta remained involved in baseball, taking on various coaching roles.