A contender but seldom a champion, he lurked for years behind Maurice Greene -- and sometimes others -- in the race to be the United States' best.
Then on a late summer day in Paris three years ago, Montgomery's world changed.
The small-in-stature sprinter took down track and field's biggest record, the 100-metres mark Greene had held for three years.
Utilising a near-perfect start and an aiding wind at the maximum allowable for record purposes, Montgomery clocked a startling 9.78 seconds, one hundredth of a second faster than Greene's 1999 record.
Montgomery was the first man to better the disgraced Ben Johnson's 9.79 set at the 1988 Seoul Olympics -- a mark wiped from the record books after the Canadian's drugs downfall -- and his time shocked many.
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"You have somebody who has not gotten the respect they deserve and they have quietly crept their way up," training partner and current girlfriend Marion Jones told Reuters after Montgomery set the record.
WIND GAUGE
Greene had other words.
"Luckiest man on earth," the former record holder told friends.
He noted Montgomery never would have received credit for the record had the wind gauge at the IAAF Grand Prix Final been a fraction higher than its 2.0 metres per second reading.
Indeed, fortune seemingly had found her way into Montgomery's life after years of trials and tribulations.
In 1994 the self-described South Carolina-born "country boy" had been denied a world junior 100 metres record of 9.97 seconds because of a slightly short track and a faulty wind gauge. Now not only had he become the king of sprinters, but he was dating sprint queen Jones. They would have a son named Monty in 2003.
A promoter's dream the couple appeared to be -- the world's fastest man and the woman who had left the 2000 Sydney Olympics with five medals, three of them gold.
All did not glitter, though.
Shortly after the world record, Montgomery and then Jones left coach Trevor Graham and they briefly worked with banned Canadian coach Charlie Francis.
The move prompted world-wide criticism for the couple, who are now directed by Montgomery's former university coach, Steve Riddick.
Both have been linked to the BALCO doping scandal, although neither has failed a doping test and only Montgomery has been charged with a doping offence by the U.S. Anti-Doping Agency (USADA).
BANNED DRUGS
The anti-doping agency, in charges Montgomery is appealing against to the CAS, has accused the 30-year-old sprinter of taking a cocktail of banned performance-enhancing drugs, plus human growth hormone and the blood-booster EPO as early as 2000.
Although Montgomery has denied taking banned steroids, the USADA wants a lifetime ban for him. Its case is based on evidence obtained in the federal investigation of the Bay Area Laboratory Co-Operative (BALCO), which is at the centre of an international doping scandal.
The San Francisco Chronicle reported that Montgomery, despite his public denials, admitted to a federal grand jury that he had taken banned steroids.
Montgomery told the grand jury that BALCO founder Victor Conte gave him weekly doses of growth hormone and a steroid-like drug known as "the clear" over an eight-month span ending in the northern summer of 2001, the Chronicle reported.
Even Montgomery's quest for the world record had its genesis in a BALCO office, the San Jose Mercury News reported.
Conte, Graham, Francis and a bodybuilder met the sprinter in late 2000 to map out a strategy for Montgomery to break the world record, the Chronicle reported Montgomery as telling the grand jury.
The plan, called "Project World Record," fell apart in a squabble over money, the Mercury News reported.
But two years later Montgomery had his world record.
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