In 2000, Dolan (through a family trust) bought the
Cleveland Guardians (then Indians) of
Major League Baseball (MLB) for $323 million from
Richard E. Jacobs, who, along with his late brother David H. Jacobs, had paid $35 million for the club in 1986. Jacobs had taken the team public in 1997. As part of the deal, Dolan bought all of the stock at just over $12 a share, making the franchise privately held once again. During his time as owner, the team experienced periods of competitiveness, including playoff runs in
2007 and
2013, and making it to the
World Series in
2016, as well as periods without success, including several seasons with over 90 losses. While the team's player salaries were among the highest in MLB during Jacobs's final years as owner, at times they have been among the lowest under Dolan. This led some fans to regard Dolan as
miserly, although other fans dispute the reputation. After the team reached the
2016 World Series, the team acquired free agents
Edwin Encarnación and
Boone Logan. However, both of these players were with other teams by 2019 in an attempt to reduce payroll, thus adding to both sides of the “miserly” argument between fans. In 2006, Dolan started
SportsTime Ohio to broadcast the team's games; in 2012, it was sold to
Fox Entertainment Group. In November 2021, the baseball team officially changed its name to the
Cleveland Guardians. At the time of his death in February 2025, Dolan and his family were the longest tenured ownership group in the team's franchise history. His son
Paul, who has held ownership duties and the title of "Owner/CEO/Chairman" of the Cleveland Guardians since 2013, is also the only one of Larry J. Dolan's six children to have held major leadership roles with the team. ==Personal life and death==