11 players who regretted leaving Liverpool as Trent Alexander-Arnold exits

Leaving a club the size of Liverpool is a huge decision for any footballer – and this lot all came to regret their choice to leave Anfield.

As Trent Alexander-Arnold announces his decision to move to Real Madrid, many former Reds will be reflecting on their own decision to leave prematurely.

We’ve picked out 11 players who should’ve stayed at Liverpool with the benefit of hindsight.

Philippe Coutinho

Little did they know it at the time, but the formation of Jurgen Klopp’s great all-conquering Liverpool team can probably be traced back to the sale of Coutinho in 2018.

Having received £200million for Neymar six months previously, Barcelona panicked and splurged a huge proportion of that world-record fee on signing Coutinho.

Liverpool reinvested the cash they received far more wisely by using the cash they received for the Brazilian playmaker to bring in game-changers Virgil van Dijk and Alisson.

Coutinho was a wonderful player, capable of producing extraordinary moments, during his time at Anfield.

But he was never able to recapture that at the Camp Nou.

The fact that he’s currently on loan, back in Brazil, from Aston Villa speaks volumes about how things have gone for him.

Georginio Wijnaldum

Wijnaldum was a key cog in a Liverpool midfield that won the Champions League and Premier League in successive seasons, notching 97 and 99 points respectively.

Part of a wider theme here with players Jurgen Klopp got the best out of, Wijnaldum sought a new challenge when his contract expired in 2021 and reportedly rejected Ronald Koeman’s Barcelona for better wages at PSG.

He failed to impress in Paris and was loaned out to Jose Mourinho’s Roma after just one season. But he suffered a broken leg and failed to kick on at the Stadio Olimpico.

Nowadays, he’s turning out as the captain of Al Ettifaq in the Saudi Pro League. Surely he’d have been better served staying at Anfield?

Fernando Torres

On the one hand, Torres left Liverpool and went on to win the Champions League, scoring one of the most iconic goals in Chelsea’s recent history at the Camp Nou and sealing their spot in the 2012 final in the process.

While that’s undeniably true, El Nino was never the same player in Chelsea blue as he was in Liverpool red.

Struggling for confidence and consistency, he looked unrecognisable to the fearless forward who used to bully Nemanja Vidic for sport.

You only need to look at the numbers. Torres scored 81 goals in 145 appearances for Liverpool, but only 45 goals in 172 outings for the Blues.

Michael Owen

For the record, Owen still defends both his decision to leave Liverpool for Real Madrid in 2004 and his goal tally during his short-lived time in Spain.

Sixteen goals from a season in which he saw limited game time isn’t as bad as you might think, to be fair.

But Liverpool won the Champions League immediately after the striker departed and you can divide Owen’s career into two distinct categories: his time at Anfield and his time after.

The first where he was one of the world’s best strikers and scoring goals for fun, and the latter where he was serviceable at best for Madrid, Newcastle, Manchester United and Stoke City.

To be fair, recurring hamstring injuries probably have more to do with that than the team he happened to be representing, but the trajectory nevertheless coincides.

Robbie Fowler

For Liverpool fans, Fowler wasn’t just a player; he was ‘God’.

Over a 17-year stint, the striker became an unquestionable Liverpool legend, netting a whopping 120 Premier League goals in just 236 appearances.

But a falling out with Gerard Houllier, who preferred the more prosaic Emile Heskey as Owen’s strike partner, saw Fowler leave for Leeds in 2001.

His time at Elland Road was followed by a spell with Manchester City, with Fowler not quite recapturing the magic of his Liverpool days.

A return to Anfield in 2006 was an admittance from the player and perhaps the club that ‘God’ should never have been allowed to leave.

Peter Crouch

Crouch has previously confessed that leaving Liverpool for Portsmouth in 2008 was the ‘biggest club regret’ of his career, admitting he would’ve loved to have been a ‘one-club man’.

“It would have been brilliant to be a one-club man or to spend 10 years at a particular place,” the former England striker told the Daily Mail in 2020.

“My biggest club regret is leaving Liverpool too early, but circumstances meant I had little option.”

Seeing the likes of Andriy Voronin and David Ngog lead the line 18 months later stung.

“Watching them getting chances, I couldn’t help but think I left too early,” Crouch admitted.

READ NEXT: Where are they now? The 17 Liverpool players who left after winning the 2020 title

TRY A QUIZ: Can you name Liverpool’s top 25 Premier League appearance makers?

Sadio Mane

Mane is only three months older than Mohamed Salah.

But, while the Egyptian King continues to tear it up for Liverpool, Mane soon dropped off the footballing map completely after leaving Anfield in 2022.

His move to Bayern Munich was nothing short of a disaster, and after coming to blows with Leroy Sane, he was unceremoniously shipped out to the Saudi Pro League.

The Senegal international might be pottering along for Al-Ittihad, but surely he could’ve played for Liverpool for a few more years at least.

Jordan Henderson

Informed by Jurgen Klopp that he would no longer be one of the first names on the team-sheet after an indifferent 2022-23 campaign, Henderson decided it was time to seek pastures new.

Those pastures turned out to be in the Middle East, as Henderson moved to Saudi Arabia to reunite with Steven Gerrard at Al-Ettifaq.

The move would be a disaster for the midfielder, shredding his previous reputation as an LGBTQ ally and only lasting six months before scampering back to Europe.

Henderson now plays for Ajax and is on the verge of captaining the Dutch giants to the Eredivisie title.

READ: Jordan Henderson & 7 other footballers that absolutely f*cked it with ill-advised transfers

Emre Can

Despite being offered a new contract at Liverpool in 2018, the German midfielder rejected the extension and signed a bumper deal with Juventus instead.

“I had a lot of offers from very good teams,” Can said at the time.

“I decided to come to Juventus because I think the project here is very big. They have very big aims. I want to be part of the project here.”

Ultimately, the move didn’t really work out and Can had to watch from afar as the Reds won the Champions League and Premier League over the next two seasons.

Ian Rush

Rush never really settled at Juventus, although that famous “it was like living in a foreign country” line is by all accounts apocryphal.

Liverpool’s all-time top goalscorer believes that his short stint in Italy actually improved him as a footballer for his second wildly prolific spell on Merseyside.

“At Juventus I learned to be a better all-round player,” Rush told FourFourTwo.

“I went to Italy as a goalscorer and came back a better footballer. At Liverpool, because we had such a great team, my job was just to be in and around the box.

“In Italy I was around the pitch more, getting back to the halfway line and everything.”

That’s fair enough. But he only scored seven Serie A goals, never won anything with Italy’s most dominant force, and surely wouldn’t have returned to Liverpool so soon if he’d delivered in Turin.

If you’re not counting Juve, you can count Leeds after his second Anfield farewell.

He only scored three Premier League goals for the Yorkshire club in an instantly forgettable footnote to a remarkable career.

Nick Barmby

With 23 England caps under his belt, Barmby was part of that golden Liverpool era around the millennium when the Reds won an unprecedented cup treble.

In 2002, at the peak of his powers, Barmby swapped Anfield for Elland Road, inking a deal with Leeds United.

He’d joined Leeds at just the wrong time; the bankrupt Yorkshire outfit were relegated two years later with Barmby having made just 25 appearances.