"You're the manager of Liverpool and you've bought Van Dijk for £75million. I'm going to give you £150m for him - would you take it?" he said on Sky Sports' The Debate.
"There would be enough people out there willing to give you £150m now and they'd give you more for Alisson at £67m and Mohamed Salah at £40m. That's a £100m player.
"The point I'm making is them Liverpool signings, not all of them, Keita has it all do, Fabinho still has it all to do, the others have improved. They are worth more money.
"You look to the Man United list now. Which one of them players is worth more money now?
The pundits discussed Man United's transfer situation on The Debate (Image: GETTY )
Mourinho's uner immense pressure this season (Image: GETTY )
"Yes of course Alexis Sanchez as he cost them nothing in the first place but no-one is taking Alexis Sanchez with the money that he earns at Manchester United."
Appearing alongside Sherwood on the show was Chelsea Women boss Emma Hayes who joined the ex-Tottenham manager in highlighting United's flaws.
"The strategy of recruitment in itself is an art," she said. "Liverpool's strategy is clearly well-defined, it involves multiple people and it's done over a period of time.
"Manchester United, I don't know what their recruitment strategy is. It's clearly disjointed.
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Chelsea women's coach Emma Hayes gave her views also (Image: GETTY )
"You can see in the way they play, they don't possess the leaders. You don't know in recruitment what you're going to get.
"You could sign a player, they may not settle, they may not speak the language quickly, lots of things go wrong in recruitment - even though you think you have a fantastic player coming in.
"Manchester United have to start at the top. It's not about Jose Mourinho, it's about everything from recruitment, not just short term strategies.
"Was Sanchez the right signing for Manchester United - regardless of the fact he was a free? Or did they need perhaps a different type of player."