When anti-gambling activist Kathy Gilroy won $25,000 by playing a sweepstakes at a gambling café in Illinois, she saw it as a fortunate windfall, if one that was a bit ironic.

Gilroy Illinois gambling sweepstakes

Kathy Gilroy won $25,000 through a sweepstakes held by a gambling company she has opposed in the past. (Image: Erin Hooley/Chicago Tribune)

But some in Illinois instead saw a case of hypocrisy from someone who had long worked to prevent the spread of gambling throughout the state.

Gilroy has long been one of the most visible opponents of gambling in the state, having worked both against the spread of legalized gaming and to shut down contests that were operating outside of state law. Just last year, she stopped a $1.6 million raffle held by the Veterans of Foreign Wars (VFW), forcing it to hold off on drawing prizes until it received the proper gaming licenses.

Efforts such as those have often been controversial, particularly when the “illegal” raffles were benefitting good causes. Previously, Gilroy had also shut down a raffle for needy college students because it was similarly unlicensed.

Sweepstakes Held by Café Company Gilroy Has Battled in Past

But she has also targeted efforts to expand legalized gaming throughout the state. Recently, she has been a leading voice against the expansion of video poker cafes, asking towns and cities to maintain their bans on gambling machines.

Those campaigns made it all the more surprising when news broke that Gilroy had won her prize at a local Stella’s Café in her hometown of Villa Park. That chain, operated by Laredo Hospitality, has been on the other side of many of these local debates over the expansion of gaming throughout Illinois.

“It’s ironic that someone who’s anti-gambling would enter something like that,” said Morris VFW Commander Jerry Zeborowski. “That’s a little hypocrisy there, don’t you think?”

Sweepstakes Was Free, Completely Legal

While Gilroy admits that the situation is unusual, she says that the fact that the sweepstakes was both free and legal differentiated it from the gambling operations she has opposed in the past.

According to Gilroy, she signed up for the café’s emails, which is where she heard about the free sweepstakes. That led to her visiting the venue to collect free scratch-off cards, which eventually led to her becoming a finalist in a drawing for a new Ford Mustang convertible. After winning the live drawing on December 16 in Rosemont, she opted to take $25,000 in cash rather than the car.

Gilroy says that she felt guilty about taking money that may have come from the losses of gamblers, but decided that the money was coming out of Laredo’s profits. She also consulted a pastor, who told her she should keep the cash.

“He said ‘Don’t feel guilty. You just got paid for all your volunteer work against gambling,’” she said. “It’s God showing his grace on me.”

Still, there are aspects of her victory that could be problematic given her anti-gambling stance. For instance, winning the prize required signing an agreement that Laredo could use Gilroy’s photo for promotional purposes. That said, given her track record as a public face against the gaming industry, the company may not want to include her in their next ad campaign.