Newly released emails have exposed the relationship between Kathy Ruemmler, former Obama White House counsel and current Goldman Sachs chief legal officer, and convicted sex offender Jeffrey Epstein, revealing personal exchanges alongside professional advice.

On Thursday (February 12), the Department of Justice published emails showing Ruemmler sent Epstein birthday wishes in 2015, writing, "I hope you enjoy the day with your one true love. :-)" Epstein responded with sexually explicit comments about male anatomy, to which Ruemmler replied, "Hard to believe that there is still an open question about whether men are [the] inferior gender."

The exchanges are part of hundreds of emails reviewed by CNN that detail their relationship, which Ruemmler has described as "friendly in that professional context."

Beyond legal discussions, the emails reveal personal elements of their relationship. In some messages, Ruemmler expressed gratitude for their "friendship" and signed off with "xo" and "xoxo." The documents show Ruemmler inquired about visiting Epstein's private island and thanked him for gifts, including what she described as "Jeffrey boots, handbag, and watch."

Ruemmler also appears to have helped Epstein navigate potential public relations challenges. In 2015, when ABC News planned a Good Morning America segment featuring Virginia Roberts Giuffre, who alleged abuse by Epstein, Ruemmler coordinated strategy with Epstein and his associate Ghislaine Maxwell. The interview never aired.

In a statement to CNN, Ruemmler's spokesperson Jennifer Connelly said Epstein "was a man of a thousand faces" and that Ruemmler "only saw the one he put on to win people over." Connelly added that Ruemmler "has deep sympathy for those harmed by Epstein and if she knew then what she knows now, she never would have dealt with him at all."

The emails also reveal Epstein helped arrange a White House tour for filmmaker Woody Allen and his wife Soon-Yi Previn in December 2015. According to ABC News, Epstein contacted Ruemmler to facilitate the visit while President Obama was away in Hawaii.

Goldman Sachs has stood by Ruemmler, telling CNN, "It's well known that Epstein's MO was to do unsolicited favors for and provide unsolicited gifts to his many business contacts."

The House Oversight Committee, which has been investigating how the federal government handled Epstein's cases, has expressed interest in questioning Ruemmler about these communications.