Chris Hero started his wretling career in the summer of 1998 in Ohio and other places arounf the country throughout the end of the 90's. His first nring name was "The Wifebeater", inspired by the white wifebeater t-shirt he would wear to the ring to wrestle in. This was short lived until a women's group was offended by this and he changed his name to Chris Hero. He debuted in IWA Mid -South where in his first year, he defeated Colt Cabana, Ace Steel, and American Kickboxer and challenged Sabu for the NWA Heavyweight Championship, in which he was not successful. He won the IWA Mid-South Heavyweight Championship four times during his time there, even facing CM Punk on a few occasions.

He moved to Chikara, where he teamed with CM Punk, and CZW where he found great success winning the CZW Heavyweight title, the Tag Team titles with Claudio Castagnoli and becoming their longest reigning Ironman Champion. He also teamed with Castagnoli in Chikara becoming their first Campeonesde Parejas. During this time, he was also feuding with Ring of Honor on behalf of CZW where he lost a title match against champion Bryan Danielson. The war between the two promotions was eventually won by ROH but CZW put on a good showing.

After the CZW vs. ROH feud, Hero returned to ROH and feued with Nigel McGuiness and the Briscoe Brothers. He was unsuccessful in obtaining the ROH World Title and the Tag Team titles. At Survival of the Fittest 2007, Hero eliminated Austin Aries, Roderick Strong, Claudio Castagnoli, and the Human Tornado to win the tournament and pick up a title shot against McGuiness once again. He made McGuiness submit but the matchwas restarted when the referee saw McGuiness reachd the ropes and he won the restart. Hero continued to run through the ROH roster even defeated Lance Storm in a grudge match but lost to ROH champion Jerry Lynn May 2009.

In December 2009, Hero once reunitied with Castagnoli to reform "The Kings of Wrestling" and jumped The Briscoe Brothers and posed with their Tag Team belts.