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I am working with clauses with adverbial meaning, and here is my sentence:

Were I to win the lottery, I would have all (of) that money spent fast.

Keep in mind that I have to express condition.

Which of the following sentences can correspond to one above?

Winning the lottery, I would have all that money ......

Having won the lottery, I .....

By/With winning the lottery, I would ....

In my opinion, I would pick and use last one( with "by/with" preposition).

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I'm sorry to differ with you, Alex, but of the three alternatives you provide, only the second, which begins "Having won the lottery ..." expresses conditionality. You really cannot use "by" or "with" along with "winning the lottery" there to do the job you're wanting it to do.

BUT--even the second option is awkward and overly formal. Well, mostly awkward. Here are some preferable constructions:

  1. If I were to win the lottery . . . [That's just your original sentence with an "if" at the beginning, but it's grammatical English.]

  2. (Colloquial.) If I won the lottery, I'd spend all the money fast. This construction is the one you would be most likely to hear anywhere but at a formal speech or in a formal essay. In other words, even though the subjunctive is proper to use, ("were to win,") often English speakers use the indicative, a breaking of the rules that renders the expression colloquial. ("If I won.")

There are many examples where the subjunctive is proper, but hardly ever used:

  • If I were a millionaire, I'd ... usually you hear

  • If I was a millionaire, I'd ...

  • If you should fall in love with him, you would become miserable. usually you hear

  • If you fell in love with him . . .

Ahh. English nerds like me (should be "like I") are fond of using the subjunctive and using "shall" and "will" properly. Almost NOBODY in the United States uses "shall" where it should be used. In Britain, the use of shall, correctly, is more frequent, but still not very frequent.

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  • I was thinking about using Having won, but I thought it was incorrect since we are using perfect to express meaning of event that occurred before one in main-clause. Now, you have proved that is not the case. Thank you!
    – Alex TheBN
    Jan 14, 2020 at 11:15
  • I have also found in my Grammar that usage "with" will express reason. (=because);
    – Alex TheBN
    Jan 14, 2020 at 11:24

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