Before Wednesday morning, Bobby Rush was best known as the one politician to ever have beaten Barack Obama in an election. The congressman from Chicago’s South Side made headlines for wearing a hoodie while speaking on the chamber floor in support of Trayvon Martin, and getting himself booted from the podium for not adhering to the dress code.

Rush is both a longtime Washington insider and a well-liked representative of Chicago’s South Side, an overwhelmingly Democratic district that boasts the country’s highest percentage of black voters (65 percent). Those two characteristics helped Rush rout the current president when he was challenged as an incumbent in the 2000 election, and also seemed to influence his Wednesday stunt that included a pair of oversized sunglasses.

“He was blinded by his ambition,” Rush said of Obama in the New York Times in 2007, when the then-senator had just launched his campaign for the White House. “Obama has never suffered from a lack of believing that he can accomplish whatever it is he decides to try. Obama believes in Obama. And frankly, that has its good side but it also has its negative side.”

The 65-year-old Rush himself bursts with confidence, boosted by 10 terms in Congress, winning nine of them with 80 percent of the vote. The drubbing of Obama in 2000 was his closest contest since winning office in 1992, still doubling his opponent, 61 percent to 30 percent.

But while Rush has ingrained himself as the “only man to ever beat Obama” in the minds of many Americans, he had been rather quiet on the issue of Trayvon Martin prior to Wednesday. His Twitter account—one place where the Trayvon case gained steam on the national stage—did not mention Trayvon until Wednesday, when Rush spoke on the floor of the House.

Yet Rush has championed civil rights for much of his career, last year penning a column honoring the late Martin Luther King Jr. In honoring King, Rush scolded the country for not moving forward on the issue of minority rights. “If [King] were alive today, I believe he would demand that the nation take a hard look at the mass incarceration of young black and brown men and women that has eviscerated too many communities in our nation.”

Strong identification with the Trayvon case could also come from a tragedy in Rush’s own life. In the fall of 1999, his 29-year-old son Huey was shot and killed in Rush’s district in Chicago as the incumbent waged his campaign against Obama. The killer got 90 years in prison.

While beloved by many in his district, Rush is facing challenges by six others for his seat this fall. He has also been criticized for his ties to top communications companies, including AT&T and Verizon, that are among his largest donors. Last year the Color of Change group called out Rush for his coziness with the industry, a claim he shrugged off.

Before the Georgia native became an ordained Christian minister in the 1960s, he served in the U.S. Army and later helped found the Illinois chapter of the Black Panthers, a group Rush later said was “glorifying thuggery and drugs,” but didn’t regret his involvement.

Rush’s display on Wednesday was not out of the blue. In February, he cohosted an event with the Discovery Channel and the NAACP about unsolved hate crimes. He also used headline-grabbing language in the fall of 2011 when he likened the NCAA to the Mafia: [it] “would make the mob look like choirboys … I have this innate understanding of the NCAA, and I think it is one of the most vicious, most ruthless organizations that was created by mankind.” Rush was holding a roundtable to discuss recruiting, financial compensation for athletes, and scholarship terms.

After claiming that “racial profiling has to stop” while sporting his hoodie on the House floor, Rush took to the TV cameras outside the chamber, wearing hoodie, sunglasses, and all. “Just because someone wears a hoodie does not make them a hoodlum.”