I don't think he will flop either, I reckon he could get 40+ goals a season in all competitions for us, considering the amount of chances we make. But Wenger will over analyse every negative possible outcome and bottle it. He is just afraid of spending big money, it doesn't help that some of his most expensive signings (Reyes, Wiltord, Arshavin, Giroud, Jeffers, Gervinho, Van Bronckhorst, Eduardo) have not worked out either.
To be fair, out of those players you mention, Reyes was a really good buy but he couldn't handle the ****ty weather. Wiltord scored plenty of goals and some really important ones for us, he was part of a great team and his goal won us the league at OT. Arshavin was decent player to buy too, but turned out to be a lazy ****, Eduardo was another good buy, Arsenal career ruined by a bad tackle. Even Van Bronckhorst, although he didn't stay long was a quality addition by Wenger. The only turkey in there is Jeffers, bit of an obvious one though.
I'm not saying all (or any) were Wenger's fault. More to say that most of his big money buys have not worked out for one reason or another and it could put doubt in his mind.
