The Owner

In 2009, when the Ricketts family was getting ready to buy the Cubs, occasionally someone would ask Tom Ricketts: Aren’t you worried about aligning yourself with a franchise best known for not winning the World Series?

Ricketts had a much bigger fear.

He was nervous that the Cubs, who had decent teams back then, might win the World Series before he could buy the team. Ricketts, who was making the bid for the Cubs along with his two brothers, sister and parents, wondered if his family would want to own the Cubs without the World Series drought.

“It’s much better to be part of the quest for a championship than to be coming in after the goal has been accomplished,” Ricketts said last week. “Our question was: If they win the World Series, do we care anymore?”

The Ricketts family, whose fortune derives from TD Ameritrade, the brokerage founded by the patriarch Joseph Ricketts, need not have worried that the Cubs would shatter its hopes. As soon as the Rickettses took charge, the Cubs fell apart, losing an average of about 93 games during the next five seasons.

Ricketts, the ownership’s public face, was nearly an everyday presence at Wrigley Field during those seasons, as he is now, making himself available to fans as he walks through the concourses at almost every home game.

He often rides a commuter train to his downtown Chicago office, where he also runs an investment banking company he created in 1999. Raised in Nebraska and a Cubs fan since he went to college in Chicago — he and his brother once lived across the street from Wrigley Field — he is one of the most accessible team owners in American sports.

“When we were losing 101 games one season, everyone assumes I walked through Wrigley and had everyone yelling at me,” he said. “That wasn’t the case at all. Every once in a while, there would be somebody who didn’t understand our plan, but we could buy them a beer and try to explain.”