Susan Walsh AP
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Property records in Camden County show that Shepard pledged one of the Lake Ozark vacation homes he co-owns with DeStefane as collateral in 2007, and again in 2013, as additional security for a letter of credit related to his affordable housing development business, Sugar Creek Finance Co.

The total amount of the letter of credit was about $17 million in 2014, according to property tax records.

Business Partners

When Shepard and DeStefane formed Black Hawk Partners and bought the first lake house in 1997, the two men already had been in business together nearly a decade. Shepard had yet to meet McCaskill, who was Jackson County prosecutor.

During deposition testimony in 2007 related to a wrongful death lawsuit filed against Reliant in 2003, DeStefane said he had known McCaskill’s husband since 1985. He said that Shepard approached him a few years later with an opportunity to become involved in a management role with his nursing home companies.

DeStefane acknowledged in the deposition that Reliant did not carry professional liability insurance from late 2000 until late in 2006.

He testified that initially the decision not to carry insurance was Shepard’s. DeStefane said Shepard – who was chief executive officer of Reliant in 2000 – had told him that liability insurance premiums were too costly. “The marching orders I got is that we cannot afford liability insurance and we’re going to go forward without it,” DeStefane testified.

Since 2007, Reliant says, the company has carried full liability insurance by an outside carrier.

Shepard and DeStefane were partners in the nursing home business from the late 1980s until Shepard separated himself from Reliant’s operating companies in 2002 and 2003, not long after he married McCaskill. She said at the time she wanted to avoid any conflict of interest.

Shepard still held an interest in partnerships that owned some of the buildings and land that Reliant rented for some of its nursing home properties, however.

LaBombard said Shepard fully divested himself of Reliant’s properties by Jan. 1, 2008, the date the Justice Department’s allegations of fraud begin. On that date, the final transfer of Joseph’s stake in such a partnership was completed, LaBombard said.

He said the senator has never had any business ties to DeStefane and her husband no longer has any connection to Reliant Care, although Shepard and DeStefane remain partners in other business ventures.

Those ventures include three companies that own property and equipment used by a surgical center next door to one of DeStefane’s nursing homes in Moberly, Mo.

Shepard is not involved in the day-to-day operations of the center, LaBombard said.

McCaskill married Shepard on April 27, 2002 in a ceremony at the waterfront vacation home he co-owned with DeStefane. She pledged her marriage wouldn’t halt her efforts to investigate the nursing home industry as state auditor.

“I will continue to work for a major overhaul in the way this industry is run and the way it is funded,” she said in a February 2002 article, two months before her marriage.

“Are his homes run perfectly? I’m sure they are not,” she said of Shepard, who was then CEO of Reliant. “Do I know he wants to give good care? I do. And do I love him? Absolutely.”

McCaskill had conducted about 70 investigations into Missouri’s nursing home industry since her election as auditor in 1998. Some of the audits probed the state’s Medicaid reimbursement system for nursing homes, others looked at problems with staffing at the facilities and lax inspections.

In 2000, she testified before Congress, explaining that Missouri did not have enough inspectors and leveled weak penalties for violations

“It takes years to get sanctions imposed, and when they are, you get pennies on the dollars,” she told the committee.

McCaskill’s efforts, as she pointed out in her memoir “Plenty Ladylike,” led to the passage of a 2003 law reforming Missouri’s nursing homes and strengthening state oversight.

“I was proud of my record as auditor, going after troubled nursing homes and protecting seniors,” McCaskill wrote.

Lindsay Wise: 202-383-6007, @lindsaywise