It’s easy to forget that at one stage Lionel Messi could have joined Manchester City , while Erling Haaland could have ended up across town at Manchester United . Would the entire course of Premier League history have changed if Cristiano Ronaldo had moved to Arsenal instead of United in 2003?
Here we pick the top transfer “what ifs” for the biggest clubs in England that could have had major ramifications — good or bad — on the future of each side in recent years.
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MAN CITY : What if they had signed Messi in 2020?
Five titles in six years (and the treble this season) suggests that City have done OK without signing Messi, but the club were ready to spend £100m to bring him to the Etihad from Barcelona in 2020 — a year before he begrudgingly had to leave his boyhood club to join Paris Saint-Germain on a free transfer. Messi is arguably the greatest player of all time and would have surely kept City in titles, perhaps even making the difference in the elusive Champions League a bit earlier.
The club wouldn’t have moved for £20.8 million winger Ferran Torres , but could also have missed out on £61.6m defender Ruben Dias due to financial limitations that year, which would have been a huge mistake given he has been one of the best defenders in the Premier League. Jack Grealish also wouldn’t have made a £100m move from Aston Villa in 2021.
Messi could have flourished under Pep Guardiola and City’s brand (which has suffered against their rivals globally) would have had a massive shot in the arm. But as much as it would have been a joy to see Messi test himself in the Premier League, City probably made the right call on this one.
ARSENAL What if Ronaldo had joined instead of Man United in 2003?
This one could have changed the entire course of the Premier League as we know it. While Ronaldo won three back-to-back titles (2006-2009) at United and forged a father-and-son relationship with manager Sir Alex Ferguson, it’s easy to imagine him doing the same with Arsene Wenger and Arsenal. And he could have done!
The Gunners were “one step” away from landing the teenager from Sporting CP before Ferguson snapped him up for £12.24m after spotting his talent during a preseason encounter against United in 2003. But, since their “Invincibles” season in 2003-04, the club haven’t won another title.
The Portugal international would have hastened the end of Freddie Ljungberg’s career on the right wing, but it’s also possible Wenger could have turned him into a central striker to replace Thierry Henry in 2006. Is it possible he could have scored even more goals in his career from that position? Either way, he still would have ended up at Real Madrid eventually.
CHELSEA : What if Steven Gerrard had joined in 2005?
Liverpool legend Steven Gerrard playing in the blue of Chelsea? It seems hard to imagine, but it was close to happening before the England midfielder made a U-turn and opted to stay at Anfield.
Chelsea (bankrolled by the millions of owner Roman Abramovich) made a reported £37.5m move and Gerrard was tempted after picking up the Champions League following that incredible comeback in Istanbul. Arguably the greatest Premier League player never to win the Premier League, Gerrard would surely have lifted more silverware at Chelsea and, playing with Frank Lampard, could have formed one of the best midfields ever with Claude Makelele behind them. Jose Mourinho’s 4-3-3 would have certainly got the best out of the pair, unlike their efforts in a 4-4-2 with the England national team.
Chelsea won back-to-back titles in 2004-05 and 2005-06 without Gerrard, but if they had signed him then they may not have had lifted only one more in the next eight years. They would have been dominant. And he wouldn’t be able to walk the streets of Liverpool anymore.
MAN UNITED : What if Ole Gunnar Solskjaer had landed Haaland in 2018?
Solskjaer managed a teenage Haaland at Norwegian side Molde before he became a superstar with FC Salzburg , Borussia Dortmund and now Man City, whom he joined for £52m last summer. But the former United manager says he told the club to sign the striker for £4m in 2018 before he took charge at Old Trafford that December, only for them to refuse. Haaland’s 52 goals in 53 games this season at City (plus 86 in 89 at Dortmund and 29 in 27 at Salzburg) suggest he would have made quite an impact at United, even at a young age.
Perhaps Haaland did exactly what was needed for his development by choosing a gradual increase in quality, rather than being thrown into Premier League life at 18, especially as Mourinho would have been his first manager. Life in the Old Trafford pressure-cooker has proven too much for many a young player and Haaland’s City connections (his dad Alfie played for them from 2000-2003) wouldn’t have afforded him much time to settle from the fans. Would he have won the treble in his first season though? Unlikely.
LIVERPOOL : What if Philippe Coutinho had stayed in 2018?
Coutinho would surely have been happier if he had never left Anfield in January 2018. The Brazil midfielder hit double figures for goals in his final three seasons (2015-2018) and was considered one of the best around before his £135m move to Barcelona ruined his career — in spite of the fact he picked up the silverware (2x LaLiga titles, 1x Copa del Rey at Camp Nou; 1x Bundesliga, 1x DFB Pokal and 1x Champions League on loan at Bayern) he left for.
Liverpool used the money to bring in Virgil van Dijk (£75m), Fabinho (£40m) and Alisson (£56m). Without the strength in depth from those players, the club wouldn’t have ended their long Premier League title drought or probably have won the 2019 Champions League either. Coutinho was class in a red shirt, but it was the right decision to let him go.
Still, Liverpool boss Jurgen Klopp told Coutinho in May 2017: “Stay here and they will end up building a statue in your honour. Go somewhere else, to Barcelona, to Bayern Munich , to Real Madrid , and you will be just another player. Here you can be something more.” So perhaps he would have had a statue outside Anfield if he had stuck around.
TOTTENHAM What if Harry Kane had joined Man City in 2021?
In this alternate reality, we’re assuming that City haven’t signed Messi a year earlier, and instead they choose to spend £150m to bring in Kane from Tottenham Hotspur instead of £100m to sign Grealish. City could have missed out on Haaland the following season if they had chosen Kane, but let me float this possibility too: they play them both together. Kane in a No. 10 role, where he has often drifted in recent years anyway, and Haaland ahead of him.
Tottenham lose their star but use the £150m burning a hole in their pocket to sign Tammy Abraham from Chelsea (before he joins Roma), or perhaps Ollie Watkins from Aston Villa, both for around £40m. Plus they have another £100m to strengthen their depth around the rest of the squad and while 2021-22 was dominated by the quality of Liverpool and City, Spurs would have put themselves in a much better position to mount a top-four challenge this season.
Yes, they lose a legend. Their greatest-ever goal scorer. But Kane would have a Premier League title in his trophy cabinet (he might have actually bought a trophy cabinet) and Spurs would have set themselves up to be less reliant on one player.
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