As we’ve covered previously, Missouri Senator Claire McCaskill (D) is facing a battle to retain her seat in 2018.  In a red state that went for Donald Trump by 19 points, she is vulnerable and her would-be Republican challengers are licking their chops.

Just as she has benefited in the past from opponents’ gaffes, McCaskill has demonstrated she is not immune to her own bungles. But her real weakness may stem from her longstanding friendship with nursing home executive Rick DeStefane. Yesterday, the Kansas City Star ran a detailed — and troubling — account of the many clouds hovering over and around DeStefane and his nursing home company, Reliant Care Group. The article is lengthy, but a group focused on defeating McCaskill’s re-election bid, Missouri Rising Action, provides a helpful summary:

For her part, McCaskill has attempted to distance herself from DeStefane’s shady track record. From the KC Star article:

McCaskill would not talk to The Star or McClatchy for this story. Her spokesman, John LaBombard, said the senator was vaguely aware that DeStefane was involved in a civil dispute with the Justice Department through her family friendship with him.

She didn’t know details about the dispute, LaBombard said.

The senator’s personal relationship with DeStefane and her use of their shared vacation property at the lake don’t present any conflict of interest with her work in the Senate, he said.

But this glosses over the lengthy history McCaskill’s husband, Joseph Shepard, has with DeStefane.

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.

So, while McCaskill is busy snarking about where Josh Hawley resides, expect her longstanding connection to DeStefane (not to mention the questions which have repeatedly arisen in relation to Shepard’s own business dealings and his benefiting from stimulus funds) to keep McCaskill’s finances and friendships front and center in this hotly contested race.  Stay tuned!