Jason Kipnis, known for his time as a second baseman, began his Major League Baseball career with the Cleveland Indians. Drafted in the second round of the 2009 MLB Draft, Kipnis quickly rose through the minor league ranks, making his MLB debut with the Indians in July 2011. His early performances hinted at the potential he would later fulfill, as he quickly became a regular fixture in the Indians' lineup.

Kipnis's breakout season came in 2013 when he was selected for the All-Star Game. That year, he posted a .284 batting average, hit 17 home runs, and drove in 84 runs. His ability to combine power with speed was evident as he also stole 30 bases. This performance solidified his reputation as a reliable offensive player and a strong presence at second base.

Throughout his tenure with the Indians, Kipnis was known for his consistency and ability to perform in clutch situations. In 2015, he again earned an All-Star selection, finishing the season with a .303 batting average, 9 home runs, and 52 RBIs. His performance helped the Indians remain competitive in the American League Central Division.

One of Kipnis's most memorable seasons came in 2016 when the Indians reached the World Series. During the postseason, he played a crucial role in the team's success, hitting .290 with 4 home runs and 8 RBIs. Although the Indians ultimately fell to the Chicago Cubs in a dramatic seven-game series, Kipnis's efforts were widely recognized and appreciated by fans and analysts alike.

Injuries began to affect Kipnis's performance in the following years, but he remained a valuable player for the Indians. In 2017, he dealt with shoulder and hamstring issues, which limited his playing time and impacted his statistics. Despite these setbacks, he continued to contribute to the team, providing veteran leadership and experience.

Kipnis's tenure with the Indians came to an end after the 2019 season when the team declined his contract option, making him a free agent. In 2020, he signed a minor league contract with the Chicago Cubs and made the team's Opening Day roster. During the shortened 2020 season, Kipnis played in 44 games, hitting .237 with 3 home runs and 16 RBIs. His time with the Cubs allowed him to play for his hometown team, as he grew up in the Chicago area.

After the 2020 season, Kipnis became a free agent again.