It is mind-boggling to think how the footballing landscape may have looked had Gerrard ended up joining Jose Mourinho at Chelsea. The local boy who had come through the club's ranks told Liverpool in July 2005 that he wanted to leave. Fans did not take the request well, burning Gerrard's number 17 shirt just over a month after he had captained the Reds to a famous Champions League triumph in Istanbul.
Having turned down a new deal, the midfielder revealed it had been "the hardest decision" for him to tell the Reds he needed to move on. The lure of working with Mourinho at the Blues appeared too great to ignore, or so it seemed. Instead, Gerrard changed his mind. "He wants to stay. I couldn't be more delighted," chief executive Rick Parry said in a news conference, echoing the feelings of Liverpool fans around the world. 'Stevie G' ended up sticking around at Anfield for another decade, eventually departing for MLS in 2015.
Ronaldo has made a habit of suggesting he is ready to move on after winning the Champions League. The Portuguese superstar got his wish after lifting the trophy for a third straight year with Real Madrid in 2018. He teased his departure in a post-match interview not long after the final whistle against Liverpool, before the confetti was even cleaned up, paving the way for a sensational switch to Juventus.
However, Manchester United were not so forthcoming to Ronaldo's wishes in 2008. So strong was the Red Devils' stance in the face of interest from Madrid, Alex Ferguson claimed United's owners, the Glazers, would rather sit a player in the stand "just to prove a point", rather than be forced to make a sale. The English club made a complaint to FIFA concerning Madrid's public pursuit (no action was taken, by the way) as they stood their ground. Having little option but to stay put, Ronaldo said in October he could see himself staying at United beyond the 2008-09 season. Yet when Madrid came calling again the following year, the forward finally got his move. United cashed in on their prized asset for a then world-record fee of £80m.
Rooney sensationally declared his intention to leave Manchester United (for the first time) in October 2010, citing a concern over the club's unwillingness to spend big in the transfer market. Following a meeting with the then-chief executive David Gill, the England international released a strongly worded statement that said: "He did not give me any of the assurances I was seeking about the future squad". Citing a desire to win trophies, Rooney suddenly appeared to be heading for the Old Trafford exit.
Manchester City seemed his most likely destination, too. However, it turned out he just needed to sleep on it. Well, for two nights anyway. Having initially baulked at signing a new deal at United, the striker made a stunning U-turn and penned a five-year contract. "I've spoken to the manager and the owners and they've convinced me this is where I belong," he said, while adding his intention to win back the trust of the fans. It may also have helped make up his mind that the Red Devils reportedly doubled his wages.
In the 2013-14 season, Suarez was sensational for Liverpool, a one-man wrecking ball who so nearly fired them to the title. The Uruguayan scored 31 Premier League goals to win the competition's Golden Boot, while he was also named the Professional Footballers' Association Player of the Year. Yet it is easy to forget that the same player had wanted to leave the Reds prior to the campaign.
Suarez believed the club had failed to deliver on a promise to let him leave after they failed to qualify for the Champions League, with Arsenal appearing his next destination. The player felt, in such circumstance, his contract included a release clause set at £40m - and the Gunners duly put in an offer £1 above that amount. "They gave me their word a year ago and now I want them to honour that. And it is not just something verbal with the coach but something that is written in the contract. I'm not going to another club to hurt Liverpool," Suarez said at one stage. In the end, he had to wait 12 months to eventually get his move elsewhere - and Liverpool pocketed considerably more than £40m when the striker, serving a four-month ban at the time from all football-related activity after biting Italy defender Giorgio Chiellini at the World Cup - headed to Barcelona.
Liverpool had barely finished typing out a statement to confirm he was not for sale when Coutinho e-mailed a transfer request to the club in August 2017. Barcelona - with money to burn after Neymar had moved to PSG - had seen two bids rejected for the Brazilian playmaker, who had signed a new long-term deal in January but made clear his desire to move on just six months later.
The Reds, however, refused to budge - "maybe we are not a selling club," said Jurgen Klopp, who integrated the player back into the squad when the window closed. However, when it ticked into 2018, the rumours started again. Having stood their ground previously, Liverpool changed their minds and negotiated a reported £142m price for Coutinho - a huge profit on the £8.5m they spent to bring him in from Inter. "It is his dream and I am now convinced there is nothing left at our disposal to change his mind," Klopp admitted. In an added twist, Coutinho found himself suggested as a makeweight in a deal to bring Neymar back to Barca before joining Bayern Munich on loan.