In Richard Arnold's chat over a pint with Manchester United fans there was one moment where he hinted at some of the mistakes the club has made in recent years.
"Do you want me buying the players? Does that not ring a bell?," Arnold said when discussing transfers with the protestors. The inference was clear and Ed Woodward's desire to try and control footballing issues often backfired.
One of the most significant issues from the Woodward era was United's policy of handing out new contracts as a way of protecting player values. In what is now a challenging transfer market, it has made selling unwanted players difficult and left the club lumbered with some high earners who are on the periphery of the first-team squad.
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Maybe the clearest example is Eric Bailly, who signed a new three-year contract in April 2021 and has played 13 games in 14 months since putting pen to paper. He ended this season behind Phil Jones in the pecking order and will almost certainly leave this summer, but United's hand in negotiations has been weakened, rather than strengthened.
Since taking over from Woodward at the start of February, Arnold has tried to do things differently. He has empowered heads of departments to focus on their strengths and that means greater responsibility for football director John Murtough to make decisions.
This transfer window is a major test of Murtough's skills, with the drawn-out pursuit of Frenkie de Jong already feeling like its success or failure will have a major bearing on the assessment of United's summer.
But how contract negotiations are handled will also be instructive, given United have got themselves into trouble with unnecessary extensions that were rarely earned. The departures of five senior players on free transfers this summer should signal a change in approach.
There are another raft of contracts expiring next summer, although many will have the option for a further year. Players like Fred and Luke Shaw look certain to get extensions, and probably Diogo Dalot too. Marcus Rashford will hope the impact of Erik ten Hag makes a new deal attractive to both parties.
Phil Jones will probably leave this summer and a decision on Cristiano Ronaldo will clearly be made later in the season. Of all the decisions to be made the most interesting might be around David de Gea.
The goalkeeper's contract expires next summer, although United have an option for a further year. He's coming off the back of an excellent season, but there are legitimate questions around his suitability for Ten Hag's system. It feels like the 31-year-old has something to prove going into 2022/23.
The issue around a new contract is complicated by the renewal De Gea was given in the summer of 2019, at a time when his form had been questionable for several months. That deal made him the best-paid goalkeeper in the world, on around £375,000 a week. Giving him an extension into his mid-30s on a similar salary would be a questionable decision.
De Gea will retain his status as United's No.1 next season and Dean Henderson will depart this summer, with a loan move to Nottingham Forest edging closer to completion, but it feels like 2023 will be a decisive date for United's goalkeepers.
That will be the summer to settle on a plan for De Gea, who will have either proved he is capable of playing under Ten Hag, or United can let him go and look at alternatives. Rushing into an extension now isn't necessary.
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