One of U.S. Secretary of Education Arne Duncan’s most trusted advisers is returning home to Chicago.

Peter Cunningham‘s last day is Nov. 30. His official title is assistant secretary for communications and outreach; in reality, he helped shaped the department’s—and Duncan’s—message and served in the secretary’s inner circle. (And, he’s quite the musician to boot.)

With President Barack Obama’s second term about to begin, you can expect more departures from the Education Department. Already, Karen Cator, the department’s education technology director, has announced she’s leaving. In August, federal special education chief Alexa Posny departed. I’m curious to see how long Joanne Weiss, Duncan’s chief of staff, and Ann Whalen, the department’s director of implementation, stick around. As the hard work of implementing Race to the Top and other key programs continue, these two have been at the department since almost the beginning. And, they hold key roles.

Cunningham came with Duncan from Chicago and was the guy who handled some of the trickiest political and policy issues—from a scandal in Chicago over admissions into top schools when Duncan was the district’s leader to whether common core equaled a national curriculum. And, he was probably instrumental in one other thing: getting Arne Duncan on Rolling Stone’s hot 100 list in 2009 of folks changing America, in which the secretary placed ahead of singer Taylor Swift.

In a goodbye email today to colleagues, friends, and others, Cunningham wrote: “It has been an eventful and rewarding four years working for a great President and a great Secretary on an issue of critical importance to our economy and our future.”

Taking his place as acting assistant secretary will be Massie Ritsch, who is the deputy assistant secretary for external affairs and outreach.