Rumors have been swirling for months about the future of Conn’s Hospitality Group, with some people speculating that owners Court and Karen Conn may be leaving town or filing bankruptcy.
Karen Conn recently sat down with SBJ and confirmed that while there are changes in the works, it is not nearly as dramatic as some people believe.
“Court and I have made a decision that it’s time for us to strategically plan,” she said, noting that he will be turning 78 in September. “How much longer do we want to keep doing this?”
Karen said that while Court has already stepped back somewhat from the business, he still comes in once a week or so and is also involved in other aspects. She said that when his oldest son, Casey Conn, left the family business in 2023 that caused them to think about the future of CHG.
“There wasn’t any bitterness; we were very supportive of Casey’s decision to do something else that was his passion,” Karen said. “But why are we going to take this to our grave when there isn’t anybody coming up behind us?”
Karen noted that Court’s father died at age 83. “In business, as an entrepreneur, you plan your own retirement or someone is going to plan it for you after you’re dead,” she said. “We want to enjoy whatever time we have left.”
With no heir apparent at this point, Karen said the couple started the process by putting the properties on the market.
“We’re realistic in terms of how long this might take – it could be a five-year plan,” said Karen. While she would love to find a single buyer to take over the various business holdings, she said she realizes that it’s more likely multiple buyers will need to be identified.
“I have everything listed for sale except Obed and Isaac’s, that is being held back until we see other properties move,” Karen said. The DeWitt Wickliffe Smith Mansion at 625 S. Second St., built in 1865, currently serves as the corporate headquarters and is for sale by owner.
The other properties, including the Inn at 835, Wm. Van’s Cafe and Obed and Isaac’s Peoria location, are listed with Dan Sperry, a Springfield-based commercial broker who specializes in business sales through his company, The Business Exchange.
Karen said the recent change of plans with Wm. Van’s Cafe became a lesson for her in due diligence. On April 15, local entrepreneur Dalton Ingram announced he would be purchasing Wm. Van’s Cafe as of May 1 and renaming it Mary Todd’s Cafe, continuing to operate out of Vinegar Hill Mall, another property owned by Conn’s Hospitality Group. But just a few days later, CHG issued a statement rescinding the announcement: “After careful consideration and discussion with our team, we will not be proceeding with the sale as initially planned,” said an April 18 post on Wm. Van’s Facebook page.
Karen said that while she initially was impressed by what she believed was Ingram’s passion for historic properties – he and a business partner had previously operated Springfield Carriage Company, a restaurant in a historic building across from the Lincoln Home site – she later discovered things in his background that concerned her.
Karen emphasized that while the couple hopes to transition into retirement, they are committed to making sure the properties and businesses end up in good hands
“We’re not going to sell to any willy nilly off the street; this isn’t about taking the money to run,” she said. “We’ve done all this in the hopes that our legacy lives on.”
The Conns purchased the Vinegar Hill Mall complex in 2021 and opened Trish & Mary’s Public House, the first new venture in the space, in 2023. That was followed by Wm. Van’s Cafe in 2024, but other plans, such as adding a winery, haven’t materialized. Karen said they ran into licensing issues that limited their ability to obtain a license to produce wine since Conn’s Hospitality Group already has a retail license.
“If I’m able to sell some of my other retail-licensed businesses, then there wouldn’t be an issue to move forward with the winery,” Karen said. “That’s a challenge I would like to take on.”
However, she said she’s open to passing the Vinegar Hill Mall property on to someone else.
“My goal was to save it. We’d like to find somebody to come in and finish renovating it,” Karen said.
While the Conns wait to see who expresses interest in purchasing the various properties, Karen said things will continue to be “business as usual” for Conn’s Hospitality Group. “We are still committed to keeping operations going strong every single day. This is just a strategic, long-term plan for us to be able to retire and exit.”
This article appears in SBJ August 2025.