Barry was courted by the Reds in consecutive summers, 2008 and 2009, but snubbed them in favour of Manchester City on the latter occasion.
After four successful seasons at the Etihad Stadium, during which time he won the Premier League and FA Cup, Barry finally made the switch to Merseyside with Liverpool's city rivals Everton.
And ahead of Wednesday night's fixture against his former suitors, the 35-year-old revealed why he never became a Red.
"I met the City manager Mark Hughes in a hotel. He emphasised the ambition of the owners. He described it as a speeding train and his advice was to jump on," Barry told the Mail.
"I also spoke to [then manager] Rafa Benitez at Liverpool but he didn't completely convince me. He said he wanted me to come in, play left-back, left-midfield, centre midfield. That's what I'd done at [Aston] Villa, it wasn't for me any more."
The previous year, Liverpool had failed to meet Villa's £18 million asking price for Barry, but later spent £21 million on Tottenham's Robbie Keane.
And the former England midfielder admitted: "That didn't personally go down well with me."
According to Barry, not even a phone call from legendary Liverpool captain Steven Gerrard could convince him to change his mind upon leaving Villa Park the following year.
He added: "Steven had heard I'd agreed terms with City and called me up. 'Are you sure you've made your mind up? Is there anything that can change your mind? Tell me it isn't the money.'
"I took it as a huge compliment Steven wanted me at Liverpool. I said it wasn't just the money, my mind was made up and Manchester City was the right one. In hindsight, it was the right decision."
Since being snubbed by Barry, Liverpool have won only one piece of silverware - the 2012 League Cup - but remain in the hunt to win this year's Europa League.