Chelsea: 288 Million in Spending / 92 in Income (-196mil)

Man City: 582.25 Million in Spending / 97.1 in Income (-485.15mil)

Barca: 305 Million in Spending / 129.5 in Income (-175.5mil)

Madrid: 460.5 Million in Spending / 181 in Income (-279.5mil)

Juventus: 257.65 Million in Spending / 96.4 in Income (161.25mil)

Inter: 227.35 Million in Spending / 172 in Income (-55.35mil)

Milan: 127.2 Million in Spending / 138.5 in Income (+11.3mil)

So every big club you mentioned has lost millions in transfers over the last few years while Milan hasn't lost anything. That should speak for itself as to some of the problem. Berlusconi can afford to spend more, but owning a soccer club is not a good business, they almost always lose money over time. Cutting the salary costs of a lot of our older players this year will allow for more spending this summer compared to last summer as Milan does spend the most on salaries in the Serie A. Basically it's about being smart. Sure we could have spent 25 million to sign a m'vila and isla for our midfield (just an example) but instead we got MVB and Nocerino for a wopping .5 mil and they were amazing. Berlusconi and Galliani are looking for these types of deals. You could view it as them being "cheap" but I personally see it as being frugal and spending their money wisely.

A possibility is that B&G were simply waiting for this day, when the team would lose 5+ of the older players before spending the money to rebuild the team. It seems very likely that this is the case, up the start of this most recent season a lot of the old players were still getting regular playing time, so rather than kick them out, B&G waited until it wasn't worth keeping them around anymore. I think we will see a focus on youth players and free agents in the next few years. The older free agents would provide experience and depth, while spending on younger players <24 would allow Milan to build a squad that would last another 10 years.

I realize I rambled a bit, but these are just my thoughts.