9 times clubs really regretted letting a star join a rival

Robin van Persie Alex Ferguson

Pig’s heads, Cruyff’s revenge and Coles on the move – what happened when these top players signed for a direct rival

Andrea Pirlo (Milan to Juventus, 2011)

The idea of a club deeming Andrea Pirlo, the most graceful midfielder of his generation, surplus to requirements is faintly ridiculous. But that’s exactly what the powers at Milan thought in 2011 when, after a decade of service, the Rossoneri allowed the 32-year-old’s contract to run down, leaving him free to join Juventus for nothing. Pirlo for free!

The playmaker had been integral to Milan’s success in the 2000s, helping them to two Serie A titles and the Champions League twice. However, in 2011, Pirlo didn't slot into Massimiliano Allegri’s system at the San Siro and, hungry to prove that he could still be an asset to a top side, he joined Juventus when his contract expired.

Juve were on the up. Pirlo joined Antonio Conte’s Turin revolution, with a new stadium and a group of players determined to reach the summit of the Italian game. Pirlo helped them achieve precisely that, notching 13 assists as the Bianconeri finished the 2011/12 league season unbeaten to clinch their first title in nine years.

Juventus went on to win four consecutive Scudetti, with peerless pass-master Pirlo at the heart of the team – all while Milan fell into decline. Milan CEO Adriano Galliani would eventually admit that allowing Pirlo to leave was his biggest mistake in football. Can’t argue with that one.

Andy Cole (Newcastle to Manchester United, 1995)

In January 1995, Kevin Keegan made a decision. The Newcastle boss decided that he no longer wanted Andy Cole, the striker who'd scored 55 goals in 70 league matches for the Magpies. Cole had been force of nature at the head of Keegan’s attack-happy side, but the manager believed that something had changed in his star man. 

When Keegan believed that Cole had been slacking in training, tensions began to simmer. After the striker was dropped, stern words were exchanged – and then, in January 1995, Tyneside was rocked when Newcastle accepted an offer of £6m (plus Keith Gillespie) from Manchester United for Cole.

The fans demanded answers and, to his credit, Keegan answered them face-to-face. He rationalised the sale as a matter of footballing judgement but, on the pitch, it proved to be catastrophic. Cole went on to win five Premier League titles with United, while the Magpies never fully recovered from a spectacular capitulation during the 1996/97 season that allowed United – and Cole – to triumph.

Johan Cruyff (Ajax to Feyenoord, 1983)

Having enjoyed not one but two successful spells at Ajax during his illustrious career, Cruyff would have been forgiven for thinking he was untouchable in Amsterdam. He was 36 in the summer of 1983 but had just helped Ajax win a domestic league and cup double. But Ajax opted not to give their greatest-ever player a new contract.

The man who'd shaped Ajax’s destiny as much as anyone was understandably incensed. His response was an emphatic middle finger in the direction of the club he'd served so immaculately – signing for their biggest rivals Feyenoord.

The Rotterdam giants had consistently underachieved in the decade after winning the league and UEFA Cup in 1974, so capturing Cruyff – albeit in the winter of his career – was a real coup. Ajax thought they’d had the last laugh when they pulverised Feyenoord 8-2 in De Klassieker, but the beaten side – buoyed by the wisdom of Cruyff, the youthful exuberance of Ruud Gullit and free-scoring brilliance of Peter Houtman – weathered that and embarked on a 15-game unbeaten run. In April, they even exacted sweet revenge on Ajax with a 4-1 spanking.

Cruyff, virtually ever-present in the team, helped Feyenoord to their first title in 10 years, a KNVB Cup, and was named Dutch Player of the Year. That’s how you retaliate.