Trent Alexander-Arnold’s much-touted move to Real Madrid appears to be edging closer but for a while now many Reds have been expecting it to happen. Most are more optimistic about Mo Salah and Virgil van Dijk and also feel that those two are more important to the club’s short-term success over the next few years.
In Conor Bradley the Reds appear to have a readymade replacement should TAA make the move that most now feel is inevitable. There is even, perhaps, a feeling that Bradley is better defensively, so whilst missing out on a fee for any top player, let alone a homegrown one, hurts, at least the starting XI should not be too badly hit by Trent’s departure.
He will not be the first much-loved, big-name player to leave the Reds. Liverpool are not a selling club but there are few sides anywhere in the world who can fend off Real Madrid when the Spanish giants come knocking. Indeed, as we will see, Alexander-Arnold is far from the first player to swap the Mersey for Madrid.
King Kev Heads to Hamburg

One of the first greats to leave Liverpool for a non-English side was Kevin Keegan. Keegan was signed by the Reds for just £33,000, a real bargain. He joined from fourth-tier Scunthorpe in 1971 and enjoyed six very good seasons with the Reds.
Initially signed by Bill Shankly as a midfielder, the manager soon decided to play the 20-year-old higher up the pitch. The switch came about due to a perceived lack of tactical discipline but the experiment to play the new signing alongside John Toshak soon came to look like a masterstroke.
Keegan went on to play 323 times for the Reds, scoring 100 goals and creating many more. In his final season with Liverpool, he scored 20 times in 57 games and left having won three league titles, an FA Cup and two UEFA Cups. In his final season, 1976/77, he also won the European Cup with Liverpool, alongside that year’s league title.
In 1977 he moved to Hamburg for a British record fee of £500,000 and improved his salary by around 500%! He had three good seasons in Germany and won the title in 1978/79, making the European Cup final the following year (Hamburg lost to Forest in the big game). His exploits saw him named European Player of the Year (essentially the Ballon d’Or) in both 1978 and 1979.
Steve McManaman Starts Spanish Exodus

In 1999, Steve McManaman left Liverpool to sign for Real Madrid on a free transfer. The “Bosman” was the biggest move of that nature since the new transfer regulations had been introduced and the Bootle boy was a brilliant acquisition by the Spanish side.
McManaman won the FA Cup and League Cup with the Reds but was unlucky to play for the club at a time when they were not quite good enough to deliver more. Macca, capped 37 times by England, would have more joy in Spain, playing a big role in their Champions League wins in 2000 and 2002. He also won the La Liga title in 2000/01 and 2002/03 and is fondly remembered in Madrid.
Five years later, and after McManaman had left the club, Real came calling for another Liverpool great, Michael Owen. Owen’s reputation has been tarnished among Reds by his subsequent decision to join Man United but as a youngster he was truly world class.
Owen helped Liverpool to a cup hat-trick in 2000/01, the Reds winning the League and FA Cup, as well as the UEFA Cup (and the 2001 Charity Shield and UEFA Super Cup too) and also won the League Cup a second time in 2002/03. In all, he netted 158 goals for the Reds from just 297 games, and his pace and finishing were second to none at his peak.
Madrid signed the striker for a bargain fee of around £8m but it didn’t work out for him in Spain. He was given few opportunities, though still netted 16 times, despite rarely being a starter. In 2005 Newcastle brought him back to the Premier League for a fee of almost £17m. Since then current Bayer Leverkusen boss, Xabi Alonso, has made the same Liverpool-to-Real move, doing so in 2009. Alonso won two Spanish Cups, the league and the Champions League with Madrid, before winning much more silverware at Bayern Munich.
Not Just Real Though

Real is not the only Spanish club that has taken a shine to Liverpool players though. Javier Mascherano moved to Barcelona in 2010 and the Argentine was a key player under Pep Guardiola. Whilst with Barca, Mascherano won four La Ligas, four Copa del Rey titles and the Champions League twice.
Despite the impressive silverware haul he won with the Catalans, Mascherano’s loss was not as painful as the two other Reds that made the same move. In 2014 Luis Suarez signed for Barca to form the formidable MSN front three, alongside Lionel Messi and Neymar. The Uruguayan netted 31 times in 33 PL games in 2013/14 but it wasn’t quite enough for Liverpool to win the title. He joined Barca for around £65m and was a big hit there, managing 198 goals in 283 games, including 59 in 53 matches in 2015/16. Suarez matched Mascherano’s league and domestic cup haul and also won the Champions League.
The Reds lost another South American to Barca but in the end, the sale of Philippe Coutinho worked out well for the club, even if it hurt at the time. The huge fee Liverpool got for the Brazilian – some £142m – allowed Jürgen Klopp to build the team that would go on to win the Premier League. Moreover, the player struggled to settle in Spain and now 32, has failed to hit the glorious heights he reached with the Reds during his six seasons there and with subsequent teams.
Mane to Munich

Coutinho was loaned by Barca to Bayern Munich but a couple of years after that one Red made the move directly from Merseyside to Munich. Sadio Mane was loved at Anfield and his partnership with Mo Salah and Bobby Firmino was behind much of Liverpool’s success.
Mane was a selfless player and hugely popular and there was little acrimony when he made his £35m switch to Bayern in June 2022. The Senegalese ace went on to play just one season in Germany, netting 12 times in 38 games and claiming the Bundesliga title.