Football League journeyman Greg Halford made “the biggest mistake” of his career by asking Roy Keane a specific question after signing for Sunderland.

The Hashtag United defender has played for an astounding number of clubs throughout his 20-year career. Now 38 and approaching the latter stage of his career, he has had plenty of time to look back on his highlights and lowlights.

And none were lower than when he first signed for the Black Cats at the beginning of the 2007/08 season, just after they had been promoted to the Premier League. With Roy Keane as manager, Sunderland made the full-back their first signing of the summer by paying Reading £3.5million for the then 22-year-old.

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But Halford immediately put himself in the fearsome Irishman’s bad books by questioning him about the direction of the club in their first meeting. And Halford has now admitted that his question - asked on the advice of his agent - was a huge error on his part.

He told the Undr The Cosh podcast: “Keane was obviously keeping tabs on me for six months. I flew up there, met him, went into his office and I was told by my agent ‘ask him these sort of questions’ like who else are you going to be signing? Because I was his first summer signing.

“I thought ‘if I’m coming from seventh placed Reading I need to know what type of players you’re going to be bringing in, what your dreams and goals are for the next season’. So I asked him that question and oh my God, the daggers that I got.

Do you think Greg Halford's questions were that bad? Let us know in the comments section.

LONDON - AUGUST 23: Sunderland manger Roy Keane gives instructions from the touchline during the Barclays Premier League match between Tottenham Hotspur and Sunderland at White Hart Lane in London on August 23, 2008.
The defender's questions did not go down well with Roy Keane

“I then read his book and he’s got a whole chapter about me, he said ‘I should’ve just pulled the plug [on the transfer] there and then.’ He just over-exaggerates everything and it just wasn’t the case at all.

“Probably the biggest mistake I made in my football career was asking him that question. From that point, he never talked to me.”

Greg Halford called it the "biggest mistake of my football career"
Greg Halford called it the "biggest mistake of my football career"

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Halford made his debut on 15 August 2007 in a 2-2 draw with Birmingham City and played the following three matches before being sent off in the third - a 3-0 defeat to Luton Town in the League Cup. He made three more appearances before being sent off again.

Unsurprisingly, his fractured relationship with Keane meant he struggled for game time and was sent out on loan to Charlton Athletic and then Sheffield United the following season. He was sold to Wolves in July 2009.