If you withdraw your bitcoin from whirlwind in multiple steps of lets say 0.1BTC to different addresses so the individual withdrawals can't be linked together then you don't necessarily need bigger deposits than the one you made yourself right?

Lets take this pool:
Deposit 1: 1,0BTC
Deposit 2: 0,3 BTC
Deposit 3: 0,1 BTC

Now you deposit 0,4 BTC and withdraw in steps of 0,1BTC. Every single withdrawal could have been initiated by any of the 4 (including yourself) deposits.