In 2005, he was stripped of his records—including a now-void men's 100-meter world record of 9.78 seconds set in 2002—after being found guilty of using performance-enhancing drugs as a central figure in the BALCO scandal.

Since retiring from athletics, he has been tried and convicted for his part in a New York–based check fraud scheme and for dealing heroin in the Hampton Roads area of Virginia.

Montgomery did not qualify for the 100 meters at the 1996 Summer Olympics, but he did compete in Atlanta in the heats of the 4 × 100-meter relay team that eventually finished second behind Canada.

In 2014, Montgomery relocated to Gainesville, Florida, to start a business focused on general athletic and sports training for youth and adults.

The motto is a reference to both the initial success, extensive life challenges and ultimate redemption reflected in his athletic and business timeline.

While he has not returned a positive drug test, according to press reports he testified to the agency that he, along with a number of other prominent athletes, obtained steroids and human growth hormone from BALCO, a laboratory near San Francisco.

On November 24, 2008, Montgomery admitted to taking testosterone and human growth hormone before the Sydney Games 4 × 100-meter relay, in which he helped claim the gold medal.

[2] After the admission an International Olympic Committee spokesperson said the committee would look into the matter as part of its open file on the BALCO investigation, but as of 2019[update] the United States team continues to be officially listed as the winner of the event[3] and no action has been taken against teammates Jon Drummond, Bernard Williams, Brian Lewis, Maurice Greene, and Kenny Brokenburr.

[8] On May 1, 2008, an indictment was unsealed that accused Montgomery of dealing more than 100 grams of heroin in the Hampton Roads area over the previous year, according to the Virginian-Pilot, the daily newspaper in Virginia Beach.