He's cheap in the sense he sets his valuations low. Everyone else will pay the going rate, Wenger feels he has some magic formula that lowers this rate and he effectively takes himself out of the active market so he can passively wait for the bargains and leftovers. The Ozil and Alexis signings - we thought - were the exception. Supposedly the start of this big new post-stadium move era. Nope. When it came to stumping up the cash to get that striker we heard the thousand and one names but no bids went in. He has a history of not paying the going price, even when the margin is a couple of million. I don't think he accepts that football is a pretty brash and vulgar business where you kick your cash in and take a gamble on getting a return. Instead he views it as an economic exercise, you calculate all the variables, apply a formula, if you get the right answer back then knock off 10% and make a derisory offer that pisses people off.
He's convinced himself we can't play in the big leagues with the likes of the chavs and the gypos. This is bullshit though because you don't have to go head to head with them, you can find other ways to assemble a good squad but sometimes that means taking a risk by paying that little extra. The joke is, once the panic stage of the transfer window comes around and we only have a few days to act, the clubs we are trying to buy from see us over the barrel and take the piss. Wenger's caution and prevarication often costs him rather than saves him money.
Everybody gets the job is a little more difficult than pressing + and - buttons and clicking the MAKE OFFER button, especially when you don't have the infinite money cheat code. But he's gone from being a prime spotter of talent (e.g. Anelka) to a doddery old git (e.g. the striker we have needed for HOW LONG NOW). And it's because he has an aversion to spending the big money that gets you into the title hunt. We could spent it (look at the 90 mill last window) but he'd rather go for 5 second tier options than one premium solution. He's a multipack, special offers guy, or so he thinks. Because I don't call 30+ mill for Mustafi much of a bargain, for example.