1someone owes a lot of money and is deeply in debt
up to his ears in debt
2registered as unemployed and receiving benefit from the government.
on the dole
3make a lot of money
make one’s pile
4having trouble covering your basic living expenses with your current income
can’t make ends meet
5extremely wealthy, someone whose fortune is excessive or offensive
stinking rich
6to pay a very small or insignificant amount of money
pay chickenfeed / pay peanuts
7having a large amount of money
loaded
9having a comfortable amount of money, good position
well off
10to be in debt or losing money
in the red
11having very little money or being short of funds
strapped for cash
12very wealthy
made of money
14have an excess of money and the freedom to spend it on unnecessary things
have money to burn
15has a lot of wealth but lacks the good judgment
more money than sense
16extremely rich and prosperous
rolling in it
17having little or no money available
skint
18destitute, with no money or resources, or physically incapacitated and weakened
down and out
19having a large amount of money / hot flow
feeling flush