Roy Keane’s time as a footballer was laden with accolades and admiration but it was not without some missteps.
Yet, when reflecting on a playing career which included 11 red cards, boycotting a World Cup and getting pushed out of Manchester United, Keane chiefly regretted not leaving the Red Devils sooner.
“I wish I bloody had!” the Republic of Ireland international seethed. “Part of me is jealous now when I see other lads going abroad because it’s a great experience for your family.”
As the end of each transfer window comes and goes, there are scores of players who are lumbered with the same pang of remorse as Keane. Here are the individuals that may carry the most regret after staying put this January.
In October, Aaron Ramsdale admitted that he was “suffering and hurting” from his sharp slip down Arsenal’s goalkeeping pecking order. Across the subsequent three months, Ramsdale has been afforded four appearances.
Arsenal’s former number one has gotten the nod for a Champions League dead rubber, two cup games and a league trip to Brentford, the latter solely because David Raya cannot face his parent club. With Arsenal out of the Carabao and FA Cups, Ramsdale’s only senior appearance between now and the end of the season will likely be the reverse league fixture against Brentford.
Had the England international secured a January move, he would not be quite so fixated with Saturday 9 March.
Thomas Tuchel’s interest in “a real defensive midfielder”, namely one “who is more concerned with defence than attacking the opposition box”, has existed since his appointment at Bayern Munich but evolved into an obsession as the summer window dragged on.
Joao Palhinha came within a whisker of fulfilling Tuchel’s deepest desires, even posing in the famous red kit before the deal fell through in the final hour. Bayern were still interested in Fulham’s midfielder heading into the winter window but prioritised the arrival of right-back Sacha Boey for £25.6m – presumably to Tuchel’s enduring chagrin.
While comfortable Premier League safety is an impressive level to reach, it remains to be seen whether a genuine European behemoth such as Bayern will be quite so keen on Palhinha this summer, as he turns 29 and still has four years left on his contract.