Ex-Portsmouth, Sheffield United and Charlton winger training with League Two strugglers
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The 33-year-old has been without a club following the expiry of his short-term contract at Northampton in January.
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Hide AdBut the 2014 News/Sports Mail Pompey Player of the Year could be set for a new chapter in his career by linking up with the League Two strugglers.
Southend are in need of some of inspiration as the battle for survival. They currently sit second-bottom after a surprise 1-0 win at Newport on Tuesday night.
Holmes could be someone manager Mark Molesley turns to in order to keep his side’s Football League status.
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Hide AdThat’s despite the former Blues favourite announcing his intention to retire with a back injury last summer – a problem which plagued his time at Sheffield United.
Holmes made 62 appearances for Pompey between June 2013 and December 2014, scoring three goals.
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Hide AdIf he links up with hometown club Southend on a permanent basis, they will represent his ninth team during a career spanning 14 years.
He's also represented the likes of Charlton, Oxford United, Barnet and Gillingham after being plucked from non-league.
Should Holmes win a deal at Roots Hall, he will become the third player with Pompey links to sign this season.
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Hide AdBlues winger Reeco Hackett-Fairchild is currently on loan at Roots Hall and has scored once in six appearances.
Ex-Fratton favourite Greg Halford is also presently representing the Shrimpers.