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Deep Pockets with Glass in the Bottom 

Your so cheap that you can't get to your money in your pockets and if you could you wouldn't because there is sharp glass in the bottom, therefore you won't try to get your money. Cheapskate.
Adam is so cheap he has deep pockets with glass in the bottom.

deep pockets/short hands

A miserly billionaire, especially when it comes to charity
Sure he's loaded, but he, he's just charity-stays-in-the-pocket kind (or unkind!): deep pockets/short hands

short arms and deep pockets with glass in the bottom 

An extremely cheap person. A miser. One who never wants to pay his own way.
Don't ask Adam to buy, he's got short arms and deep pockets with glass in the bottom.

have deep pockets and short arms 

You sir, clearly have deep pockets and short arms.

deep sockets = deep POCKETS 

What you realize must be da case if someone owns both a standard set of ratchet-wrenches and a collection of elongated ones, as well.
Many assorted tools are often available for mere pennies on da dollar at yard sales and online marketplace sites, and so da "deep sockets = deep POCKETS" assumption is not necessarily true each and every time... before you start feeling envious of someone's exTENsive --- and therefore seemingly exPENsive --- array of lengthy tubular six-and-twelve-pointers, look them over carefully to see wheter they are either particularly new-looking or even all of da same brand. If not, then realize dat these collections may merely be da "cream of da crop" from random groupings of tools in jumbled chests and toolboxes dat their present owner had obtained on da cheap from here and there, and then had merely sifted out da best specimens and carefully arranged them into those neatly-sorted sets.

My pockets run deep 

I can pay for it my pockets run deep