In 2000, Dolan (through a family trust) bought the Cleveland Indians of the MLB for $323 million from Richard Jacobs, who, along with his late brother David Jacobs, had paid $35 million for the club in 1986. Jacobs had taken the Indians 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. The sale set a record at the time for the sale of a baseball franchise.
During his time as owner, the Indians have experienced periods of competitiveness, including playoff runs in 2007, 2013, and making it to the World Series in 2016, as well as periods without success, including several seasons with over 90 losses.
His nephew James L. Dolan owns the New York Knicks of the NBA and the New York Rangers of the NHL.