It seemed a deal was signed, sealed and delivered for Gerrard to move to west London in 2005, but at the last minute, it hit a snag and was abruptly called off.
The reasons are many, but ultimately, Gerrard got cold feet and it was English football that suffered.
A year later, Chelsea signed Michael Ballack and in the process, we missed out on witnessing one of football's (potentially) greatest midfield partnerships of a generation play out.
Gerrard and Frank Lampard, individually brilliant for their clubs, never hit it off on the international stage. They rarely found the combinations that made them so lethal domestically, remaining two players at odds with each other.
Collectively, they were poor.
That fact hadn't deterred Jose Mourinho, his pursuit of Gerrard a clear indicator he was confident of achieving where Sven Goran Eriksson had failed.
With weeks and months on the training ground to drill his players, the Portuguese had a plan. Unfortunately, we've never bore witness to it.
On paper, that Gerrard-Lampard combination had it all. Goals, endeavour, energy, leadership—indeed, with his track record, it's difficult to imagine Mourinho wouldn't have made it work.
Had he, Eriksson's job would have been done for him. England would have flourished.
Now Lady Time has caught up with both players, the debate is officially over. Lampard is off to New York in May to play out the remaining days of his career, while Gerrard has confirmed this season will be his last in a Liverpool shirt.
Unless Gerrard becomes New York City FC's third Designated Player in their inaugural MLS campaign, the Gerrard-Lampard partnership will be confined to the history books once and for all.
The pair are arguably the Premier League's finest midfielders, and while English fans can only imagine what could have been on the international stage, Gerrard himself must be thinking about what would have happened had he followed through on his decision to quit Liverpool.
"This has been the toughest decision of my life and one which both me and my family have agonised over for a good deal of time," Gerrard said this week in a statement on the Liverpool website, announcing his departure.
"[...] My decision is completely based on my wish to experience something different in my career and life and I also want to make sure that I have no regrets when my playing career is eventually over."
It's almost as if that statement was written 10 years too late.
For sure, a big regret on Gerrard's part will be leaving Anfield without a Premier League winners' medal. Gerrard came close last season but failed, and this year the Reds are already out of the race, trailing Chelsea and Manchester City by 17 points.
Ironically, it was the club he snubbed that snatched Premier League glory from Gerrard's grasp. To add salt to the wound, it was Gerrard's slip that allowed Demba Ba in on goal to put Chelsea ahead at Anfield in a game they went on to win 2-0 in April.
That was supposed to be his moment. He was close, but not close enough it proved. From there, Liverpool's title challenge crumbled.
He must regret not making that Chelsea move.
In the time since, Gerrard had to watch on in envy as Chelsea lifted trophy after trophy. There have been four FA Cups, the League Cup, two Premier League crowns, Europa League and Champions League glory since he turned his back on Mourinho.
Chelsea have arguably been England's most successful club in the last decade.
By contrast, Liverpool have lifted silverware twice—the League Cup and FA Cup, struggling to live with their tag as favourites in each of those finals.
Footballers at the height of their profession earn huge salaries, but as the cliche so rightly tells us, they play for the glory of it all. Every player, elite or otherwise, wants to win.
By that measure, Gerrard would be lying if he didn't look back on his career with the hint of regret he says he is trying to avoid.
Gerrard wanted to leave Merseyside in 2005 as he had outgrown the club. His ability and ambition weren't matched by Liverpool and of all the teams interested in him, it was Chelsea who could deliver his dreams.
His head was turned, but that shouldn't be a mark against his name in the same way he shouldn't be lauded as the quintessential one-club man that he so often is.
Gerrard was chasing success and as time has shown, Liverpool couldn't deliver it.
His legacy should be so much greater. It should be one defined by silverware and success, instead the plaudits coming his way since the announcement of his Liverpool departure are that he has carried the club throughout his career.
Lampard went through similar emotional turmoil when he left Chelsea last summer. He's remembered for much more in west London, though.
Would he rather Gerrard's legacy?
Garry Hayes is Bleacher Report's lead Chelsea correspondent. All quotes were obtained first-hand unless otherwise noted. Follow him on Twitter @garryhayes