In 2009, Ricketts founded DNAinfo.com, a digital news service that used to cover neighborhood news in New York City and Chicago. Ricketts shut it down on November 2, 2017, one week after their employees voted to unionize. Gone with it were Gothamist, Chicagoist, DCist, LAist, SFist, and Shanghaiist. On the 3rd of November, 2017, archived versions of Gothamist, DNAinfo, and other sites were back up. In September 2017, Ricketts wrote, "I believe unions promote a corrosive us-against-them dynamic that destroys the esprit de corps businesses need to succeed."
In October 2009, the Ricketts family acquired a 95 percent controlling interest in Major League Baseball's Chicago Cubs and Wrigley Field, as well as 20% of Comcast Sportsnet Chicago. The Ricketts family represents the eighth ownership group in the 133-year history of the team. While Ricketts is not directly involved in the team's operations, his son, Tom Ricketts, is Cubs chairman and his three other children (Pete, Laura and Todd) are on the board of directors. In 2016, seven years after purchasing the Cubs, they won the World Series ending an 108-year-old drought without a championship.