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Mr. McAuliffe’s refusal to address a personal financial arrangement involving a company that later fell under congressional scrutiny flies in the face of his promise at a forum in May to create transparency as Virginia governor, especially when it comes to ethics.

“Transparency is important and, as you know, I’ve also called for an ethics commission when I am elected governor to make sure that we’re taking these thorny issues outside the state government,” Mr. McAuliffe said at the time, specifically criticizing Mr. Cuccinelli and Gov. Bob McDonnell, a Republican, for their lack of transparency involving gifts they received from a wealthy businessman under investigation.

Mr. McAuliffe also has promised to enact a gift ban on elected officials that he would enforce on himself through executive order if the legislature doesn’t act.

Real estate lawyers contacted by The Times described covenants not to encumber as a form of extra security or collateral.

Real estate lawyer Susan Pesner reviewed the document at the request of The Times. She described covenants not to encumber as a general form of extra security or collateral.

“Generally, a covenant not to encumber is given by a property owner in favor of the bank issuing the letter of credit assuring the bank that the title of the property will remain in the same condition as when the bank underwrote its letter of credit,” she said.

In the transaction involving Mr. McAuliffe’s home, the covenant not to encumber makes clear that the family trust entities were somehow obligated to Ullico, but the filing doesn’t shed any light on that transaction, she said.

Whatever the fine print was between Ullico and Mr. McAuliffe, the document provides further evidence of the Democrat’s cozy relationship with organized labor as he appears headed to become the next governor of a right-to-work state that historically has not been favorable to unions.

Mr. McAuliffe has made no secret of his ties to the unions while at the Democratic National Committee. In a 1997 deposition with Senate investigators looking into DNC fundraising, he said, “I dealt with a lot of labor. I was probably one of the most active and visible people on the outside who dealt with labor.”

Mr. McAuliffe’s name surfaced among Republican lawmakers years after Global Crossing’s bankruptcy in 2002. At the time, lawmakers questioned whether Mr. McAuliffe was involved, though he was never an executive at the telecommunications company. Asked whether he thought Mr. McAuliffe played a role in the Ullico stock deal, future House Speaker John A. Boehner, Ohio Republican, told The Hill newspaper in 2003, “I don’t know, but I intend to ask.”

Ullico’s investment strategy at the time was headed by Michael Steed, according to The Hill. He previously worked with Mr. McAuliffe at the DNC. Neither Mr. Steed nor Ullico responded to inquiries from The Times.

In 1997, Mr. McAuliffe went to Mr. Steed at Ullico about real estate deal in Florida, The Wall Street Journal reported years later. The newspaper found that Mr. McAuliffe persuaded Ullico to come through on a $20 million loan to construct a movie theater in a shopping center as part of a development in which he was involved at the time.

The newspaper reported that while Mr. Steed initiated the loan, the loan itself appeared to be a straightforward commercial transaction.

But it’s unclear whether that transaction was tied to the one involving Mr. McAuliffe’s house.

Another land filing in November 1999 noted that the debt secured by the covenant not to encumber had been “fully paid or otherwise discharged.”