Senator Russ Feingold of Wisconsin nominated him for the medal in 2002 and, following a lengthy investigation, the U.S. Army approved the nomination in February 2010.
A series of late night phone calls by Enyart to the general manager of the Kenosha, Wisconsin station which carried his program but publicly disagreed with Enyart's views prompted Senator Russ Feingold to call for a Federal Communications Commission (FCC) investigation to see if any laws had been broken by the talk show host.
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On January 22, 2010, United States Senators Herb Kohl and Russ Feingold forwarded four names to the Obama White House for consideration to fill the vacancy on the Seventh Circuit Court of Appeals created when Judge Terence T. Evans assumed senior status.
Frequent targets of his commentary include Republicans known for their pork barrel spending, such as Senator Ted Stevens, and both Democrats and Republicans who support campaign spending regulations, such as Senators Russ Feingold and John McCain.