Ed Woodward is preparing to finally leave Manchester United at the start of February, when he will be replaced by Richard Arnold.
Many United fans would say he should have plenty of regrets about his tenure but ESPN have reported one that Woodward has.
They say that one of his biggest regrets as his time at the club comes to an end is not bringing England captain Harry Kane to Old Trafford.
Because Kane is a world class player and the best English striker of his generation, Woodward has apparently viewed him as a prime target.
Sir Alex Ferguson tended to make a point of signing the best English talent, splashing out big fees on Rio Ferdinand and Wayne Rooney when it was clear they were going to be Three Lions mainstays for years to come.
But the wealth in the Premier League now means that plucking players from divisional rivals is harder than it was in the early-to-mid 2000s, when both those deals got done.
Ferguson poached Tottenham’s centre-forward in September 2008 when they landed Dimitar Berbatov after a long, drawn-out negotiation.
United also dealt with Daniel Levy over signing Michael Carrick in July 2006 and has spoken about how hard it is to do business with him.
“We must say that negotiations were very difficult and lasted for years. Typical Daniel Levy! It was very difficult to negotiate, but in the end we got over it and he has had a great career since he joined us.”
On the Berbatov deal, he added: “The whole experience was more painful than my hip replacement!”
Negotiating with Tottenham and Levy has only got harder and he convinced Kane to sign a six-year deal in 2018, which has left him out of reach for any club since.
That is acknowledged in the ESPN report, and while United have been linked with Kane at times during Woodward’s tenure, it has never seriously looked close.
It would probably have taken a club record fee to land Kane in recent years, but United did commit to spending £75 million (BBC) on Romelu Lukaku in July 2017 before the Englishman had signed his latest Spurs deal.
Perhaps that summer, when United spent big on a striker to replace Zlatan Ibrahimovic, was the sliding doors moment.
But as Woodward prepares to step aside, there are plenty of other failures for him to reflect on.
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