A huge lifter at 2.05 m tall, Velichko Cholakov won a bronze medal as a super-heavyweight at the 2004 Athina Olympics. That year he also won the European title, coming back in 2006 to take second at the Europeans. Cholakov won a silver medal at the 2003 World Championships. In 2002 he was World and European Youth Champion.
In 2008 Cholakov had a positive steroid test in an out-of-competition test, along with several other Bulgarians, which caused Bulgaria to withdraw its weightlifting team from the 2008 Beijing Olympics. Cholakov later coached young weightlifters in his native Smolyan. He continued to compete and tried to make the 2012 Olympics, but had heart problems, which eventually caused his early death.