By Illinois Review
Money has long shaped Illinois politics, and no Republican donor has given more in recent years than Richard Uihlein. But while his checkbook has been massive, his track record has been disastrous.
In 2018, Uihlein stunned the state when he gave $2.5 million directly to State Rep. Jeanne Ives’ gubernatorial campaign and another $8.5 million to Dan Proft’s Liberty Principles PAC, which operated as a pro-Ives super PAC. Ives mounted a serious challenge against incumbent Republican Gov. Bruce Rauner, with Proft acting as the puppet master behind the scenes.
Despite the millions invested, Ives came up short, losing to Rauner, who limped into the general election damaged and bruised. The weakened governor was crushed by JB Pritzker, a political newcomer with unlimited family wealth. That race marked the beginning of the Pritzker era.
Four years later, in 2022, Uihlein went even bigger. He spent a staggering $52 million trying to elect State Sen. Darren Bailey governor, who was endorsed by Ives. Ten million dollars went directly to Bailey’s campaign, while $42 million flowed to Proft’s new vehicle, the People Who Play By The Rules PAC. Bailey dominated the primary, but in the general election he was no match for Pritzker’s money and Chicago’s Democrat machine. Pritzker coasted to reelection by double digits.
Now, Uihlein is backing another candidate – Ted Dabrowski, a former president of Wirepoints and close ally of Proft and Ives. This time, Uihlein’s opening check is just $250,000, far smaller than his previous investments.
Since 2012, the playbook has remained the same: Proft and Ives benefit from Uihlein’s funding while the Democrats celebrate and expand their supermajority in Illinois.
The history of losses tied to this network goes back further. In 2004, Proft helped recruit Maryland resident Alan Keyes to parachute into Illinois to run for U.S. Senate against then-State Sen. Barack Obama. Keyes was trounced by 43 points, a landslide that launched Obama into the national spotlight and paved the way for his presidency.
As Chicago Magazine reported in 2013, Proft was among those who pushed for Maryland resident Alan Keyes to run against Barack Obama in the 2004 U.S. Senate race in Illinois.
But for many Republicans, the pattern is clear: Uihlein’s money, combined with Proft’s strategy and Ives’ political brand, has delivered not conservative victories, but Democratic dominance. From Obama in Washington to Pritzker in Springfield, Illinois conservatives have paid the price.
The criticism is sharp. Despite his vast wealth and willingness to spend it, Uihlein has developed both a “spending problem” and a “losing problem.” Every time Uihlein writes the big checks, the Democrats end up stronger.
And the stakes for Illinois families are real. Since taking office, Pritzker has poured billions into migrant services, signed one of the nation’s most extreme abortion laws, and backed the SAFE-T Act, which gutted cash bail and put criminals back on the streets. Pritzker has also waged an assault on parental rights, pushing policies that allow boys to compete in girls’ sports and change in girls’ locker rooms.
For Ted Dabrowski, Uihlein’s $250,000 donation gives him early momentum. But with Uihlein’s history, it also ties him to a donor and network with a losing streak that has reshaped Illinois politics – for the worse.
