After the 2005 season, the Reds had endured five consecutive losing seasons, the team's longest such streak in 50 years, under the ownership of Carl Lindner. Castellini led a group that purchased the Reds from Lindner for $270 million, and in January 2006, Castellini was named the CEO of the franchise. One of Castellini's first moves as CEO was replacing General Manager Dan O'Brien with Wayne Krivsky in February 2006. The Reds were more competitive in 2006, finishing in 3rd place in the National League (NL) Central division at 80–82. In the winter of 2006, Castellini introduced new uniforms for the Reds. Under Castellini's ownership in 2010, the Cincinnati Reds won their first National League Central division championship since the 1995 season. From 2014 to 2019 they finished no higher than 4th place in the Central division including 4 straight seasons in last place, losing more than 90 games each season. In 2020 they made the playoffs in the COVID-19-shortened season with an expanded playoff field but were beaten by the Atlanta Braves, 2–0.
