Animated by disdain for President Obama, Joe Ricketts, the billionaire founder of TD Ameritrade Inc., is zealously forging ahead with a $12 million series of ads to support Mitt Romney and Republican congressional candidates despite the fact that his effort further complicates an important business proposition of his own children, according to sources at Chicago’s City Hall.

The proposition is the desperately needed upgrade of Wrigley Field, home of the Chicago Cubs, which is owned by the family of billionaire Ricketts and overseen by his four kids, notably Tom Ricketts, a bright and mild-mannered team chairman whose politics are decidedly more moderate than his deeply conservative father. Indeed, sister Laura Ricketts is an unabashed Obama supporter and fundraiser.

The father’s move, a City Hall source indicated, will further raise doubts among African-American and other legislators whose votes would be mandatory for approval of government assistance.

Word originally leaked in May that the father was plotting a $10 million super-PAC campaign to attack Obama, in part over the president’s past ties to the hyperbolic Rev. Jeremiah Wright, Obama’s onetime pastor and a favorite villain of the right during the 2008 campaign. An aide to Ricketts senior then disavowed the Wright plan and claimed it was not authored by Joe, but rather by consultants acting without his full approval.

As for Tom Ricketts, he made clear, “As chairman of the Chicago Cubs, I repudiate any return to racially divisive issues in this year’s presidential campaign or any setting—like my father has.”

But Monday’s Wall Street Journal confirmed that he would this week start airing an ad campaign, apparently to run in battleground states and to feature supposedly onetime Obama supporters discussing their change of heart and plan to back Romney. The effort is to be funded by Joe Ricketts’s own super-PAC and is part and parcel of the huge infusion of money into the presidential race via such PACs and related groups legally approved and further inspired by the Supreme Court’s Citizens United ruling.

The barrage may or may not hurt the incumbent president. But it seems certain to harm the cause of upgrading Wrigley Field, one of America’s beloved, if dilapidated, baseball stadiums. It is a virtual tourist mecca—its popularity enduring even the Cubs’ dismal performance on the field this season, which has the club 30 games out of first place going into Monday night’s combat. Alderman Tom Tunney, who represents the Wrigley Field neighborhood and has had a prickly relationship with the owners, says Joe Ricketts’s campaign was “disturbing for those of us who are backing the president.” Asked how Ricketts’s move might affect any negotiations to strike a government-supported deal to fund a Wrigley renovation, Tunney put it bluntly: “It certainly doesn’t help.”

The stadium is a 98-year-old dump in need of millions of dollars of repairs each winter. It explains why Tom Ricketts spent a significant amount of time in recent years lobbying then-mayor Richard M. Daley and is now lobbying Mayor Rahm Emanuel for city help with a planned $300 million renovation, as well as seeking state and county help. In theory, it’s the sort of assistance previously afforded other sports teams in town, notably the Bears and White Sox.

The talks hit a sky-high bump in the road with initial word of the father’s plan, with Emanuel refusing to even take a phone call from Tom Ricketts, who was believed to have not been involved in the father’s decision and to not support it. The mayor, both Obama’s former chief of staff and a fundraiser for him, was furious, as were many key Chicago and Illinois politicians. They would all play a role in any government financial package for the Cubs.

At the time, Emanuel said of the Joe Ricketts ad campaign, “It’s insulting to the president. It’s insulting to the country.”

Emanuel was knee-deep in a higher priority Monday, an ongoing teachers strike. But those familiar with the City Hall thinking noted that the Joe Ricketts endeavor would infuriate a variety of constituencies, including African-Americans, who remain staunch Obama supporters.

Emanuel’s election last year relied greatly on his friendship and work for Obama, which helped explain the huge majority of the black vote he received. To get the help that the Cubs would need from the county, city, and state, the team would surely need the support of the black caucuses at the Cook County Board of Commission, Chicago City Council, and Illinois Legislature.Ironically, Joe Ricketts is butting heads with Emanuel, recently asked to revive super-PAC efforts on behalf of Obama. But the renowned political fundraiser announced that he was suspending those efforts, at least temporarily, amid questions about whether that was the best use of his time while bargaining with the teachers union over Chicago’s ongoing school strike was heating up.