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But the former Liverpool captain stands by his career choices.
The legendary Liverpool figure explained his feelings, claiming he has had a relationship from afar with Mourinho for many years.
I know we would've added more trophies to what I've already won," Gerrard told Rio Ferdinand's FIVE.
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Gerrard was touted as the final touch to Mourinho's midfield in 2005 after Liverpool's historic UEFA Champions League triumph in Istanbul.
"I'm happy with the decision I made."
Despite ultimately missing out on the Premier League, Gerrard will forever have a deep connection with Liverpool Football Club, where he is widely regarded as one the best players of all time.
He said that winning a few trophies with Liverpool is much more special to him than winning lots more somewhere else, echoing Trent Alexander-Arnold's recent comments about the rivalry with Manchester City.
"The connection I've got with Liverpool, my hometown club, maybe underachieved at times in certain years with Liverpool," said Gerrard.
Me winning four or five trophies at Liverpool means an awful lot more to me than if I won 10 or 11 at Chelsea."
He then remembered the amazing 2006 FA Cup final where he scored a brilliant goal to help Liverpool win against West Ham.
Another Academy product, and now the vice captain, Alexander-Arnold is on the same path.
He's also lucky enough to be in a Liverpool team more than capable of winning the biggest honors, even if Manchester City serves the 'Chelsea' role of being able to win more.
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