Liverpool star’s transfer decision that terrified his boss before he made dramatic U-turn

Rafael Benitez once feared he’d be remembered as the Liverpool boss who let Steven Gerrard slip through the club’s fingers. In the summer of 2005, mere weeks after guiding the Reds to a miraculous Champions League victory in Istanbul, the unthinkable happened: Gerrard submitted a transfer request amidst strong interest from Chelsea.

Benitez, who had succeeded Gerard Houllier a year earlier, had swiftly endeared himself to the Anfield crowd through that unforgettable European campaign. But as the euphoria of their triumph faded, turmoil and tension took its place.

Tempted by Chelsea’s financial muscle and growing dominance under Jose Mourinho, Gerrard turned down several contract extensions from Liverpool, and a switch to Stamford Bridge looked all but certain. Then, in a stunning reversal, Gerrard changed his mind, bringing widespread relief across Merseyside – and, no doubt, in the Benitez household too.

“There was a point where Rafa Benitez thought he was [going to be known as] the manager who had sold Steven to Chelsea,” former Liverpool striker Emile Heskey told Prime Casino. “But it didn’t go through in the end.”

Just as fans had mixed reactions to reports linking Trent Alexander-Arnold with Real Madrid earlier this year, Gerrard became something of a pariah in certain Anfield circles. Chelsea’s interest was widely known, and with Liverpool struggling to challenge for top domestic honours, Gerrard, understandably, began weighing his options.

In the end, Chelsea’s efforts came to nothing. Gerrard reversed his transfer request and penned a new, high-value deal, pledging the peak of his playing years to the Reds. At the time, he famously declared: “If I win a couple of trophies at Liverpool, it would mean an awful lot more to me than to win 10 at Chelsea.”

In the end, Gerrard got his wish – at least in part. He added two more pieces of silverware to his cabinet with Liverpool: the 2006 FA Cup and the 2012 League Cup. However, the Premier League title – the one honour he craved most – remained agonisingly elusive.

Meanwhile, Chelsea continued reaping the rewards Gerrard knowingly sacrificed. Over the next several years, the London outfit accumulated an impressive haul – multiple league titles, domestic honours, and the coveted Champions League trophy in 2012.

Though Gerrard ultimately followed his heart, the price he paid was steep. Heskey, however, firmly believes his former team-mate made the correct call in staying.

“He’s a local lad, and he’s become a legend. It’s difficult when you’re leaving your local team, especially when it’s Liverpool or you’re leaving a Manchester club, and you’re such a big legend within the city,” said Heskey, who spent four-and-a-half seasons at Anfield.

“Going to, say, Chelsea or Arsenal or someone like that is going to be tough when you come back with a London team. If you’re going abroad, it’s not as bad, even if Trent was getting grief recently.

“But as we saw with Michael [Owen], as we saw with [Steve] McManaman, and players like that, it’s not as bad. But when you go to Chelsea, like Steven almost did, that’s tough. I believe it was right for him to stay even though he probably would have won league titles if he left.”

Despite his dedication, the Premier League crown continued to evade Gerrard’s grasp, though not without a couple of agonising near-misses. Under Benitez in 2008/09, they pushed Manchester United all the way, ultimately finishing just four points adrift.

Then came the 2013/14 season – perhaps the most gut-wrenching of all. With Brendan Rodgers at the helm, Liverpool mounted a thrilling and unexpected title charge, powered by Gerrard’s veteran leadership and the attacking brilliance of Luis Suarez, Raheem Sterling, and Philippe Coutinho.

But with only three fixtures remaining, a fateful slip against Chelsea of all teams – an infamous moment now etched into football folklore – allowed Manchester City to leapfrog Liverpool and pip them to the post. As such, Gerrard’s dream of capturing the Premier League with his boyhood club, thus justifying his Chelsea rejection years before, slipped away again, for what would be the final time.