The former England captain played 717 times for the West London outfit, and went on to win five Premier League titles, five FA Cup crowns, and indeed the Champions League in 2012, with his final piece of major silverware of course their league triumph under Antonio Conte last term.
Redknapp has never made any secret of his admiration for Terry, but his hopes of finally signing him in an ambitious swoop could be dented by local rivals Aston Villa.
"Terry has been there 20 years", said Di Matteo via The Mirror.
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John Terry is now without a club after his 22-year stint with the Blues came to an end last season.
Redknapp joined Birmingham at the tail end of last season and saved them from relegation, despite a disastrous spell under the previous manager, former Chelsea legend Gianfranco Zola, report The Telegraph.
The Italian was controversially installed by the club's Chinese owners in December past year replacing the sacked Gary Rowett, who had taken them to play-off contention, but the club went into freefall winning just twice in 22 matches and led to Zola resigning.
The 36-year-old has given no indication as to where he will be playing football next season, and he even admitted that retirement was an option.