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I'm familiar with this sentence

He is a tough guy to deal with.

And I understand why there should be a with after to deal. My teacher used to say that you could un-shorten the infinitive to an attributive clause like

He is a tough guy which you will deal with.

But this sentence is confusing to me,

He has enough money to buy a racing car (with).

First, the infinitive can be unshortened to

He has enough money with which he can buy a racing car.

But it could also be unshortened to

He has enough money so that he can buy a racing car.

Does that mean I can use ....to buy a racing car and ...to buy a racing car with?

  • Never use a preposition to end a sentence with: He has enough money to buy a racing car. – Hot Licks Nov 7 '17 at 1:37
  • This is a rule with which I'm not quite familiar. – Barry Nov 7 '17 at 1:41
  • Parse it carefully. – Hot Licks Nov 7 '17 at 1:42
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    Another teacher who hasn't gotten the news that the rule about not ending a sentence with a preposition is long gone and was never a good rule. (Also consider "deal with" as a phrasal verb.) – Xanne Nov 7 '17 at 3:26
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    Xanne, Hot Licks is broadly correct, and IMHO his worst failing there was not to add unless you’re sufficiently comfortable with the language that you can happily justify your choice. I think He is a tough guy to deal with is a fine example, and works far better than He is a tough guy with whom to deal but more usefully, He has enough money to buy a racing car is just fine by itself. The other examples have their own challenges to resolve, prolly somewhere such as ell.stackexchange.com before any of them is ready to do a job here. – Robbie Goodwin Nov 12 '17 at 18:52

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