2
  1. By stealing that money he can pay all his debts

Or

  1. With stealing that money he can pay all his debts?

I think with is correct here.

Cz that'd mean

With the help of stealing that money, he can pay all his debts

  • 2
    Your first example is correct. The preposition phrase by stealing that money acts as a 'means adjunct'. It expresses the means by which he can pay all his debts. – BillJ May 25 '17 at 14:34
  • You may exlude the preposition and say, "Stealing that money he can pay all his debts" – SovereignSun Sep 29 '17 at 18:39
1

In this case it would be #1 because this use of by is on, as a means of conveyance:

They arrived by ship.

  • What if i use with? That wont sound wrong though – user55625 May 25 '17 at 15:05
  • 1
    @user236989 - With sounds wrong. By means "by means of" or "through using". With doesn't mean that. – stangdon May 25 '17 at 17:40
1

The correct answer is the first one. The preposition "by" indicates that the purpose of stealing that money is to pay all his debts.

See http://www.learnersdictionary.com/definition/by

c - used to indicate an action that is done for a particular purpose
    * You can reset the machine by pressing this button. [=you can press this button to reset the machine]
    * He began his speech by thanking the President and ended it by telling a joke.

The preposition "with" indicates what he can use to pay all his debts. There is no sense of him performing an action to pay them.

With that money he can pay all his debts.

or

With the stolen money he can pay all his debts. [The money was already stolen.]

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