In February 2010, the Spaniard made a £500,000 signing that shaped Liverpool's future.
Brought to the club by Benitez when he was just 15, the now England international has gone from strength to strength after signing from Queens Park Rangers.
This season, his role in Brendan Rodgers' squad will be crucial - and it could well end up the difference between success and failure for the Reds. After all, Sterling's contribution last term was important enough.
|Team||Pos||Goals||Assists||Dribbles Won||Successful Final-Third Passes||Apps||Mins|
As Opta stats show, the forward was his side's fourth-highest goalscorer in the Premier League, also registering five assists and completing 332 final-third passes. Most impressively, however, despite playing 700 minutes less, Sterling won just one less dribble than Luis Suarez.
Indeed, with the ability to play out wide and in the no.10 role, Sterling is one of the main reasons Rodgers believes Liverpool can still challenge at the top without the aforementioned Suarez.
If you took one look at the youngster at the beginning of last season, though, you could not have foreseen such a meteoric rise in such a quick space of time.
Sterling struggled for both pace and strength, with his form taking a serious dip as a result. Rodgers kept faith in him, kept playing him and refused to loan him out. The decision paid off.
In 2014, the 19-year-old was one of the best young players in Europe and now looks like the future for both Liverpool and England. At the World Cup, Sterling was Roy Hodgson's biggest weapon, despite being one of the youngest members of the squad.
But all of this, of course, traces back to Benitez.
In his last season at the club, the Spaniard left the Reds with a parting gift like no other. The 15-year-old boy he brought to Anfield has become one of Liverpool's greatest assets. And this season could be his time to shine like never before.