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In August 2017, Rosenberg found himself at odds with the Trump administration over the President's remarks encouraging the police "be rough" with suspects. His internal memo to the DEA workforce gained public attention for Rosenberg's repudiation of Trump's remarks. In it, Rosenberg wrote: "The President, in remarks delivered yesterday in New York, condoned police misconduct regarding the treatment of individuals placed under arrest by law enforcement... I write to offer a strong reaffirmation of the operating principles to which we, as law enforcement professionals, adhere. I write because we have an obligation to speak out when something is wrong. That’s what law enforcement officers do. That’s what you do. We fix stuff. At least, we try." The Washington Post editorial board, in a piece titled "A divided nation gets moral guidance - but not from Trump," wrote: "His letter was important not as a rebuke to the president but as a model of leadership and courage in reaffirming democratic values."

On September 26, 2017, it was announced that Rosenberg, dismayed by the Trump administration, was stepping down. His resignation became effective October 1, 2017. It was announced on October 3, 2017 that Robert W. Patterson, who had been serving as the DEA's Principal Deputy Administrator since November 2016, had succeeded Rosenberg as Acting Administrator for the DEA.

On November 13, 2017, Rosenberg initiated his role as an MSNBC contributor with an interview on The Rachel Maddow Show. He is currently a senior counsel and a member of the White Collar & Regulatory Enforcement Group at Crowell & Moring.

Rosenberg later served as Chief of Staff to the Director of the FBI (2013-15). In this role, he worked closely with James Comey and other senior FBI officials on counterterrorism, intelligence, cyber and criminal investigative issues, including with international, federal, state and local law enforcement partners.

Rosenberg was nominated by George W. Bush and unanimously confirmed by the Senate to serve as the U.S. Attorney for the Eastern District of Virginia (2006-08); previously, he was appointed by Alberto Gonzales to serve as the acting U.S. Attorney for the Southern District of Texas (2005-06).

Rosenberg was heavily involved in the government's death penalty case against convicted September 11 conspirator Zacarias Moussaoui, who was sentenced to life in prison in 2006.

Rosenberg received his B.A. (1982) from Tufts University, his M.P.P. (1985) from Harvard University and his J.D. (1990) from the University of Virginia. He was hired out of law school through the Attorney General's Honors Program and has served in numerous positions throughout the Department of Justice, including as Trial Attorney for the Tax Division's Criminal Enforcement Section (1990–94), Assistant U.S. Attorney in the Eastern District of Virginia (1994-2000), Counsel to the Director of the FBI (2002–03), Counselor to the Attorney General (2003–04) and Chief of Staff to the Deputy Attorney General (2004–05). Rosenberg has also spent time working in private practice as Counsel at Hunton & Williams (2000–02), and as a partner at Hogan Lovells (2008–13).

Charles Philip "Chuck" Rosenberg (born September 10, 1960) is the former acting Administrator of the Drug Enforcement Administration. He was appointed in May 2015 following the resignation of Michele Leonhart.