Shaun Custis told the Sunday Supplement Arsenal must win the Premier League or face reflecting on the January transfer window as a mess.
The Gunners were strongly linked with a move for the Schalke attacking midfielder Julian Draxler and were said to be in talks with the Bundesliga club over the German international's £37million buy-out clause, but rebuked their interest on deadline day and instead brought in Kim Kallstrom on loan from Spartak Moscow.
Custis, of The Sun newspaper said: "I think Julian Draxler was rather hoping he would sign.
"There are certain people at Arsenal who believed he could well have been got, but Arsene Wenger - who they've always said will ultimately make the decision and he's earned the right to make that decision - clearly just felt he was overpriced.
"The thing is it's not actually Arsene's money if you like, it's not coming out of his pocket and I don't really know what the problem was.
"He clearly does rate the player, anybody at Arsenal will tell you that he knows that player, knows him well, has evaluated him and looked in to his background and stats and he is a player that can do a good job for Arsenal. He's just not wanted to do it now."
To make matters worse for Arsenal fans, new arrival Kallstrom picked up a back injury in a pre-season beach game with Spartak and now looks set to spend six weeks on the side-lines and Custis believes the failed attempt for Draxler might haunt them in what could be a 'mess' of a transfer window.
He said: "You thought a big signing like that (Draxler) could have helped them push on. I accept he's only 20 and untried in some respects in the Premier League, but it looked like it would have been another big statement of intent and it looks doubly worse that they didn't get him but the fact they bring in Kim Kallstrom - who we all think is past his best anyway and turns out he couldn't even play to prove he's past his best."
"He's not going to play much of a part now until the end of the season it would seem. It doesn't reflect well on the Arsenal medical set-up.
"It doesn't look like very good business and if Arsenal don't win the Premier League at the end of this season, we will look back on this January transfer window and say that it was a mess."
Daily Telegraph Football Correspondent Henry Winter made it clear he felt Arsene Wenger should have been more active in the market to provide more depth to an already shallow pool of strikers.
Winter said: "Giroud has been fantastic this season, he's looked sharp and is quick around box, intelligent and has been scoring goals but if anything happens to him - who plays up there?
"I remember when Podolski burst through in 2006 and he can play through the middle and has scored goals for Arsenal since he's been back from injury, but Wenger sees him as cutting in from the left, so who is there? Nicklas Bendtner - he's not going to win you a title, whereas a fully fit Giroud will, but at some point he will need a break - I know he's had one or two games rested recently - you'd hate this to happen, but if he got injured Arsenal look incredibly light up front."