That might be from some of the sticky issues he's already had to confront since his family took over the team in October. But those restless nights also stem from the anticipation and excitement of getting the season under way — as both the guy in charge and a longtime fan.
The latest incident in Ricketts' short tenure stems from the Cubs desire to erect a Toyota sign above the left field bleachers at Wrigley Field, which some critics say would infringe on the historical ambiance of the second-oldest ball park in the majors, built in 1914.
"I think it's fairly innocuous. It won't affect any rooftops and everyone will be able to see. It's really not a big deal," Ricketts said Wednesday after a talk at the City Club of Chicago.
"I think when we see something like that that can really help the team, we should be able to. We're very committed to the preservation of Wrigley and we've shown it and we've really done it. ... We do need to keep looking for ways to increase revenues, obviously, because we have a lot of expenses."
Ricketts said the club even put up a mock Styrofoam sign this week as a test run for city officials to see how it would look and affect sight lines. A zoning commission and landmarks committee must approve the sign and Ricketts said he's confident the issue will be resolved.
Ricketts said the deal with the automaker would produce a substantial amount of revenue that would be significant to the Cubs and not affect the field or the fans.
"I respect the fact that people like Wrigley the way it is," Ricketts said. "I really do. And we are honestly more committed to preservation than anyone."
The new owners have been busy sprucing up and making renovations at Wrigley Field, including upgrades in the restrooms and players' quarters. They've removed some concrete panels so the stadium will get more sunlight.
The Cubs are also planning to build a new spring training complex in Arizona, an $84 million project, some of which could be funded by a surcharge on Cactus League tickets. Most owners of the other teams are opposed to that, including White Sox chairman Jerry Reinsdorf.
"It's not personal," Ricketts said, adding that Reinsdorf had been helpful in giving him advice as he sought to buy the Cubs. "We'll get to the end of the line. We'll get something done there. I'm confident it's just a matter of working through the legislative process."
Ricketts said the team had not yet chosen a site for the new complex because they wanted to make sure a financial agreement was completed first.
Ricketts said there had been no discussions about adding more night games or personal seat licenses at Wrigley Field. But he said he wouldn't rule PSLs out for the future.
On the team itself, he said manager Lou Piniella's future with the Cubs will be handled by general manager Jim Hendry. Piniella is in the fourth and final year of his contract.
"I think Lou is a great person and a great manager," Ricketts said. "Next year is really between Jim and Lou ... It's Jim's decision who comes in as manager."
As a longtime Cubs fan who met his wife in the Wrigley bleachers and once lived across the street from the neighborhood park, Ricketts and his family can really relate to the long-suffering fans of a team that has not won the World Series since 1908.
When he addressed the team in spring training, Ricketts said he didn't get nervous until he turned around and saw Greg Maddux, the 355-game winner who started his career with the Cubs in 1986 and is now an assistant to Hendry.
Maddux has a new job. And so does Ricketts.
"I was joking with some neighbors, like, hopefully we don't start 1-2 and everyone says, 'Same old, same old,'" Ricketts said. "It's great right now and a lot of fans have come up and said hi. Everyone is excited and respectful, they just want to get the season started."