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1.
to take, steal or lose someone's money or investments without a care or apparent concern especially when the sums are by the multi millions or billions.
to "madeoff" with somebody's pensions fund. A pun on Bernie Madoff the world's most notorious ponzi schemer who is accused of losing $50billion of OPM or other people's money.
by vson60 January 11, 2009
 
2.
Being ripped off by unscrupulous people, due to

your own complacency and being TOO LAZY to

pull out a $2 calculator. See: Embezzlement
Looks like someone in eBay is doing a "Madeoff":

December "New fees": $14.55
Line Item actual amount: $14.43 (1%)

November "New Fees" = $24.56
Line Item actual amount: $24.31 (1%)

Ebay customer support agrees there is a
computer error, has existed since 2004!

So this particular scam: SIX YEARS!

Grocers do the MADEOFF:
1 gallon milk: $3.98
half gallon: $1.98 (cheaper to buy 2 of these!)

By being a businessman: I do the Madeoff everyday!
by Kill_the_Bill January 08, 2010