The France legend, who won the World Cup in 1998 and the European Championship in 2000, moved to the Premier League in 1998, ending five-year stay with Italian giants Milan.
During his time at the San Siro, Desailly won two Serie A titles, a Champions League and a Coppa Italia in a golden era for the club where he played alongside Paolo Maldini, Franco Baresi, Roberto Baggio and George Weah.
Approaching his 30th birthday, Desailly was keen for a new challenge and looked destined to join compatriot Gerard Houllier at Anfield.
Speaking to BoyleSports, Desailly said: "I was interested in joining Liverpool in 1998, they made a good proposal.
"But the area didn't have a French school for my kids and the lifestyle was a problem compared to London.
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Man United wanted me then Spurs made a move but I had a crush on Arsenal and wanted them
I joined dream club Man United after being angry Tottenham move collapsed
"The lifestyle is probably why I joined Chelsea over Liverpool, yes.
"My wife made a real statement that she didn't want me to drive between London and Liverpool while she stayed in London and my four kids did not have a French school.
"It's one of the reasons at the time I chose Chelsea.
"Footballers are human beings, we have to deal with the internal elements that help us make decisions.
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"And small things like that sometimes make the difference, because the money will be good wherever you go.
"You are trying to make the best deal out of the proposal, but at the end of the day you don't really care.
"What you care about is also the lifestyle you are going to have on top of your football."
Arriving for £4.6million, Desailly played 221 times for Chelsea, helping the club to win the European Super Cup, Community Shield and FA Cup.
During those six years in west London he played alongside some legendary figures, including France captain Didier Deschamps and Italian football royalty Gianluca Vialli, Pierluigi Casiraghi, Gianfranco Zola and his former Milan teammate Weah.
He also formed a formidable partnership with Frank Lebeouf in his early days at the club, before taking a young John Terry under his wing as he adapted to life in Chelsea's first team.
Now one of the most decorated players in the Blues' history, how different things could have been had he ended up on Merseyside.