U.S. Commerce Secretary Howard Lutnick has said he had "limited interactions" with Jeffrey Epstein, but documents show they were in business together as recently as 2014.

Lutnick and Epstein on behalf of limited liability companies that agreed on Dec. 28, 2012, to acquire stakes in a now- called Adfin, documents released among the so-called Epstein files show. 

Epstein and Lutnick's signatures appear on neighboring pages in the contract, with Epstein signing for his Southern Trust Company, Inc. and Lutnick for a limited liability company called CVAFH I. The documents list nine shareholders in total. 

Lutnick, the former chairman of the financial services firm Cantor Fitzgerald who at one point lived next door to Epstein, in October that he and his wife Allison had cut ties with Epstein in 2005, deciding after taking a tour of Epstein's New York townhouse, "I will never be in the room with that disgusting person ever again."

However, it appears Epstein and Lutnick continued to maintain contact and emails show they and planned to in 2011. 

The following year, the couple and their four children planned a visit to Epstein's island, Little St. James, emails show. Lutnick was invited for lunch on Dec. 24, 2012, and later, Epstein's assistant on behalf of Epstein, "it was nice seeing you."

Their Adfin deal was signed four days later. 

A source close to Lutnick told CBS News "Cantor [Fitzgerald] was a small minority investor in Adfin. At the time of doing the deal, as a minority investor, Mr. Lutnick would not have any knowledge of who the other investors were."  

Eleven days after that, on Jan. 8, 2013, Epstein had his assistant forward Lutnick a document related to casino legislation in the U.S. Virgin Islands, where Epstein had his island and a variety of business dealings. A spokesperson said Lutnick "ignored the document sent to him."

When asked for comment about their business dealings and documents concerning Adfin, a spokesperson for the Commerce Department responded with a statement it had previously issued about emails showing Lutnick planning to visit Epstein's island in 2012: "This is nothing more than a failing attempt by the legacy media to distract from the administration's accomplishments including securing trillions of dollars in investment, delivering historic trade deals and fighting for the American worker. Secretary Lutnick had limited interactions with Mr. Epstein in the presence of his wife and has never been accused of wrongdoing," the statement read.

Correspondence relating to Adfin continued until at least 2014 when one of the shareholders, David Mitchell, wrote to Epstein regarding additional fundraising involving Cantor Ventures, a venture capital subsidiary of Cantor Fitzgerald. Lutnick had been president and CEO of Cantor since 1991 and was elevated to chairman in 1996. 

Also in 1996, Epstein sold a property located at 11 East 71st St. in New York to an entity called Comet Trust, which two years later sold the property to Lutnick. It became his primary residence, next door to Epstein's New York City mansion.

By the time Epstein and Lutnick agreed to buy stakes in Adfin, it had been more than four years since Epstein agreed to enter a guilty plea to Florida state charges of procuring a child for prostitution and soliciting a prostitute. The case brought forth allegations of far broader sex trafficking and victimization of girls, but it wasn't until 2019 that Epstein was charged with federal felonies including trafficking. He died in jail in the weeks after his arrest.

In the wake of the release of the Epstein files, Lutnick has been one of a broad international network of powerful Epstein associates who distanced themselves from the financier, only to be asked now to clarify relationships with him that appear to be closer or lengthier than they previously acknowledged. 

Epstein appears to have been aware of the public relations challenge he posed to people close to him. Emails show in 2017 he agreed to to a . 

"hope pr is ok," Epstein to billionaire hedge fund manager John Paulson, an organizer of the dinner. Epstein declined to take a table awarded to donors of that level, writing that Lutnick could fill the seats. 

Their relationship continued into the next year, 2018, when Lutnick Epstein apparently complaining about an expansion plan for their neighboring Frick Collection art museum.

Lutnick warned Epstein that the renovation might "block your sunlight and views."

"You should put in a letter. I'm sending a lawyer. Don't ignore this," Lutnick wrote to Epstein.