Former Arsenal defender Martin Keown has labelled Manchester United's deadline day dealings "embarrassing".
The club spent £36 million on 19-year-old Monaco forward Anthony Martial and then became embroiled in a dispute with Real Madrid after David de Gea's move to the Bernabeu fell through.
The episode unfolded on the back of United's 2-1 defeat to Swansea in the Premier League on Sunday and Keown believes it has cast the club in a bad light.
"It felt like United were rolling the dice on deadline day," he wrote in his column for the Daily Mail. "It is hard to imagine that kind of soap opera happening under Sir Alex Ferguson and David Gill. It was embarrassing."
New signing Martial has been compared to Arsenal great Thierry Henry, but Keown - who played alongside the striker during his time at the club - said the move is a big risk.
"The signing of Anthony Martial is a huge gamble," he continued. "He has been compared to Thierry Henry and if he is half as good then he will be a decent player.
"Van Gaal likes a pacey ball-carrier — he had Arjen Robben at Bayern Munich and tried and failed to make Angel di Maria that man at United — and Martial fits the bill.
"He might even be the answer to their striker dilemma but it is still a big risk to take on an uncapped youngster."
Keown also offered his thoughts over the transfer saga involving De Gea - whose move to Madrid fell through after the necessary paperwork wasn't processed before the deadline.
"Banishing him to the reserves will have done nothing to encourage him to stay. The international break now means things can start to settle down but De Gea, who stayed professional throughout the saga, must surely play on his return," he added.
"You also wonder whether Van Gaal’s treatment of De Gea and fellow Spanish keeper Victor Valdes had any influence on why one-time target Pedro ended up at Chelsea.
"We do not see what happens in the dressing room but it is a concern when former players queue up to criticise Van Gaal’s ruthless treatment. Once a relationship is broken, there seems to be no going back."
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