A controversial Clinton adviser who faced penalties for conflicts of interests under President Bill Clinton was still assisting Hillary Clinton as secretary of state, despite the fact that his consulting firm was engaged in commercial activities in countries where she worked, emails show.

Sandy Berger, who gained notoriety when he stole classified documents from the National Archives prior to testimony before the 9/11 Commission, had Hillary Clinton's personal email address and emailed her about Israel, Pakistan and terrorism in 2009.

Berger's consulting firm, the Albright Stonebridge Group, has engaged in business in more than 100 countries around the world, according to its website.

It has worked extensively in the Middle East, an area that Berger sought to assist Hillary Clinton on during her State Department tenure.

In discussing methods of dealing with Israel in September 2009, Berger said Israeli Prime Minister Benjamin Netanyahu's positioning in Palestinian negotiations "suggests Bibi is the obstacle to progress." Berger outlined a number of ways to put pressure on Netanyahu to bend to the will of the U.S., outlining guidance that was skewed in favor of Palestinian statehood.

It was not the only time Berger referred to Netanyahu as an "obstacle," although Hillary Clinton was publicly working on strengthening her relationship with Israel at the time.

Clinton asked Berger "how to gain leverage over the Pakistanis" in October 2009, emails between the two show. She had also asked Berger for advice on ways to encourage Pakistan to more aggressively pursue al Qaeda.

A "monthly thinking group" listed among Clinton's emails included Berger. Other attendees appeared to include John Podesta, Clinton's present campaign chair, and Maggie Williams, who worked at the Clinton Foundation before State.

Berger was not the only Albright Stonebridge executive with whom Hillary Clinton had regular contact. Wendy Sherman served as vice chair of Albright Stonebridge before Clinton tapped her to join the State Department in 2011.

Sherman has been deeply involved in the Iran negotiations, and her name surfaced in several Benghazi-related emails the State Department released in May. In July of 2009, Sherman complimented Clinton's appearance on "Meet the Press" from her company account. The exchange indicates Sherman had Clinton's private email address.

Months later, Sherman was sending Clinton regards before the secretary departed for a trip to Africa.

Berger's role mirrors that of Sidney Blumenthal, who emailed Clinton advice throughout her tenure, despite having business ties to at least one of the countries on which he advised her.