Was there ever going to be a scenario in which the then 20-year-old would come into the team? Jose Enrique would have to get injured—Aly Cissokho and Glen Johnson too—and even then Liverpool could play Raheem Sterling or Steven Gerrard at full-back.
But he got his chance, much to everyone's surprise, when Brendan Rodgers gave him a starting place for Liverpool's Premier League encounter with Arsenal at the Emirates—his first Premier League start since the back end of 2011-12.
Flanagan came in for the ill Johnson at right-back and didn't look back.
A solid performance against Arsenal in that 2-0 defeat was soon followed by Rodgers putting his trust in him at left-back, filling in for the out-of-form Cissokho.
Fast forward 15 appearances later and Flanagan has been one of the many highlights of Liverpool's successful season.
According to Squawka, in his 14 Premier League appearances this season, Flanagan is winning 46 percent of his tackles and 56 percent when taking on players. His pass accuracy record stands at 81 percent, and he's created eight chances.
His Roberto Carlos-esque strike for his first goal for the club against Tottenham at White Hart Lane was met with a celebration of pure bliss and emotion. Even the most cold-hearted of football fan would have found it hard not to find some joy for Flanagan that day.
Part Of The Future
His rise from young Anfield flop to first-team regular has been meteoric, and Flanagan deserves all the praise and rewards that will be heading his way.
A new deal looks to be in the pipeline and he's completely won over Rodgers, who now sees the 20-year-old as part of his long-term plans at Anfield.
Speaking to Chris Bascombe of The Telegraph, Rodgers said this week:
He has been outstanding. He reminded me of Steve Nicol against Manchester United on Sunday – a right-footed player on the left side, steady, aggressive, no fear; he’s been a revelation, and particularly in the big games.
He has made himself an important member of the squad.
If he keeps his focus and keeps working well he can do that [be a fixture in the side for years].
Flanagan has upset the odds, surprising everyone, and forced his way into a Liverpool team at a time when confidence and performance is sky high.
From a player who looked almost certain to be told to find a new club, Flanagan has worked hard to become an intelligent and key member of Rodgers' setup.
His character, drive and passion to improve himself and be part of the team is wonderful—and a delight for the Kop to see from a player who was Liverpool born and raised.
There's elements to his game he will continue to work on—pace and positional awareness being the two key areas for improvement—but Flanagan has showed he has the potential to be a very good full-back for the club.
The way Rodgers has improved a number of players at the club is phenomenal, and there's a fair argument to suggest that Flanagan, nicknamed "the Scouse Cafu," is the biggest success story of them all.