The latest tranche of Hillary Clinton’s private emails, released Tuesday night by the State Department, highlight the role played by her controversial adviser and former White House aide Sidney Blumenthal. Several emails from 2009 show that Blumenthal advised Clinton on issues ranging from British politics to the situation in Afghanistan and Iran, much earlier than previously known.

Blumenthal served as a senior adviser to former U.S. president Bill Clinton between 1997 and 2001. His role as an informal adviser to Hillary Clinton has raised eyebrows, with Republicans in Congress seeking to put a spotlight on his influence in the State Department.

Emails released earlier revealed that Blumenthal had sent Clinton more than two dozen memos related to the unrest in Libya in 2011. However, as the latest batch of emails reportedly shows, Blumenthal’s attempts to advise Clinton on diplomacy and policy began during the initial days of her tenure at the State Department in President Barack Obama's administration.

According to Reuters, the latest emails shed light on Blumenthal’s role as a middleman of sorts between Clinton and Gordon Brown, who was the British prime minister from 2007 to 2010. Additionally, in some of the emails, Blumenthal claims to be passing on information obtained directly from British government officials.

“Consensus across the board in Britain -- center, right, left -- is that the Atlantic alliance -- the special relationship -- the historic bond since World War II -- is shattered,” Blumenthal wrote in one of the emails, according to the Guardian. “There is no dissenting voice, not one, and there are no illusions. Opinion is unanimous. The bottom line is that the Obama administration’s denigration of the UK is seen as the summation of the Bush era.” 

The contents of the emails also seem to go against Clinton’s earlier claims that Blumenthal’s advice had been “unsolicited” as in many of the email threads, Clinton reportedly responds by asking follow-up questions.

The interest in the contents of Clinton’s emails stems from the fact that her use of a private account violated White House and State Department guidelines at the time. The State Department had earlier proposed releasing her emails in January 2016 but the proposal was later rejected by a federal judge, who called for them to be made public on a “rolling” basis.