The Spanish boss brought the emerging star to Anfield as a teenager but left his post months later and didn't get the chance to introduce him to the Reds' first team
Rafael Benitez's shrewd assessment of emerging talent could be the undoing of his Real Madrid team when they face Raheem Sterling and Manchester City on Friday.
Liverpool signed a 15-year-old Sterling from the youth academy of Queens Park Rangers in February 2010, five months before the six-year reign of Benitez at Anfield came to an end.
Kenny Dalglish handed the fleet-footed forward his debut in 2012 and he became a regular under Brendan Rodgers the following season, before taking the Premier League by storm alongside Luis Suarez and Daniel Sturridge as Liverpool came close to winning the title in 2013-14.
Sterling was sold to Manchester City for reported fee of £49 million this month and made a goal-scoring debut in the 2-2 draw with Roma in the International Champions Cup at the Melbourne Cricket Ground on Tuesday.
Up next for the 20-year-old is a meeting with Liga giants Madrid.
And while Benitez can call on a host of superstars, including Cristiano Ronaldo and Gareth Bale, he may allow himself a wistful moment of wondering what might have been should the England international hit the back of the net against the Blancos.
"Obviously you know we [Liverpool] signed Sterling when he was a kid," Benitez told a press conference on Thursday.
"At that moment I was really pleased with the signing, but I had to go.
"Now, at this moment, he's not our player. I could see him the other day, he was quite good. You know how good he is. I wish them [City and Sterling] all the best, though not tomorrow. "
Madrid, City and Roma have heavily rotated their teams during the exhibition tournament in Australia, with big draw cards such as Francesco Totti and David Silva playing little more than 45 minutes or less at a time.
Quizzed on how strong a line-up Benitez is likely to pick, the former Valencia, Inter and Napoli boss sought to manage the expectations of the 90,000 fans due to attend the final game.
"I'd like to make a concept clear this morning," he said.
"We are talking about the pre-season. If I can just define that, we are talking about the preparation for the season to come.
"We have a team good enough to win, we want to keep preparing for the competition that is to come in the actual season.
"We will have a good team, you can be sure of that. But we can't guarantee how many (star) players will be in the team."
Liverpool signed a 15-year-old Sterling from the youth academy of Queens Park Rangers in February 2010, five months before the six-year reign of Benitez at Anfield came to an end.
Kenny Dalglish handed the fleet-footed forward his debut in 2012 and he became a regular under Brendan Rodgers the following season, before taking the Premier League by storm alongside Luis Suarez and Daniel Sturridge as Liverpool came close to winning the title in 2013-14.
Sterling was sold to Manchester City for reported fee of £49 million this month and made a goal-scoring debut in the 2-2 draw with Roma in the International Champions Cup at the Melbourne Cricket Ground on Tuesday.
Up next for the 20-year-old is a meeting with Liga giants Madrid.
And while Benitez can call on a host of superstars, including Cristiano Ronaldo and Gareth Bale, he may allow himself a wistful moment of wondering what might have been should the England international hit the back of the net against the Blancos.
"Obviously you know we [Liverpool] signed Sterling when he was a kid," Benitez told a press conference on Thursday.
"At that moment I was really pleased with the signing, but I had to go.
"Now, at this moment, he's not our player. I could see him the other day, he was quite good. You know how good he is. I wish them [City and Sterling] all the best, though not tomorrow. "
Madrid, City and Roma have heavily rotated their teams during the exhibition tournament in Australia, with big draw cards such as Francesco Totti and David Silva playing little more than 45 minutes or less at a time.
Quizzed on how strong a line-up Benitez is likely to pick, the former Valencia, Inter and Napoli boss sought to manage the expectations of the 90,000 fans due to attend the final game.
"I'd like to make a concept clear this morning," he said.
"We are talking about the pre-season. If I can just define that, we are talking about the preparation for the season to come.
"We have a team good enough to win, we want to keep preparing for the competition that is to come in the actual season.
"We will have a good team, you can be sure of that. But we can't guarantee how many (star) players will be in the team."
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