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When given the following problem:

A) Bill took the money.

B) That shows his character.

Turn clause A into a nominal clause or phrase and make it the subject of b.

I came up with three grammatical possibilities:

1) That Bill took the money shows his character.

2) For Bill to take the money shows his character.

3) Bill's taking the money shows his character.

None sit well with me. One and two don't seem to work just 'cause I wouldn't say either. Number three, the one that turns clause A into a gerund phrase, is better except for it's possessive subject in bold.

Does the subject of a gerund phrase have to be in the possessive in standard English?

"Bill taking the money shows his character" sounds more natural to me.

William
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    "Bill took the money, and that's a clear reflection on his poor character. But the fact that my teacher is making me combine those statements in a awkward way is even worse." – Hot Licks Oct 11 '15 at 19:09
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    @HotLicks "The fact that Bill took the money..." is what I would say, but we aren't supposed to add any nouns. – William Oct 11 '15 at 19:13
  • @William Failing to use the possessive with a gerund still sends some teachers to the fainting couch, but in simple cases (like your examples) either one is acceptable. Some people detect a slight difference in meaning, and more complicate phrasings will require abandoning the possessive. Check here for a good discussion and pointers to more: http://english.stackexchange.com/questions/2625/when-is-a-gerund-supposed-to-be-preceded-by-a-possessive-pronoun – deadrat Oct 11 '15 at 20:39
  • Both the first and the third sentences sound OK to me. (So does "Bill showed his character by taking the money," but that's not what the problem asked for.) The second sentence, with "For," sounds to me as if Bill hasn't (yet) taken the money but might do so. In that situation, I'd say "For Bill to take the money would show his character." – Andreas Blass Oct 11 '15 at 20:50
  • Bill Stickers is innocent. – Edwin Ashworth Oct 11 '15 at 23:21

2 Answers2

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You're right -- none of those sit right. They have heavy subjects, and English doesn't like that.
There are a lot of syntactic rules that fix this; the most common are Extraposition and Clefts, of one kind or another.

In this case, here are some sentences that sit better, all from the prescribed clauses, all synonymous:

  • It shows his character that Bill took the money. (Extraposition)
  • What shows Bill's character is that he took the money. (Wh-Cleft)
  • It's Bill's taking the money that shows his character. (It-Cleft)
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John Lawler
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  • Oh, as for the subject of a gerund -- it can be either possessive (Bill's, his) or it can be objective (Bill, him). But it can't be nominative (*he). – John Lawler Oct 12 '15 at 00:39
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Introduce an expletive to the sentence:

If Bill took the money, that shows his character.

As for your question concerning the subject of gerund phrases, they must certainly be genitive.

Bill's taking of the money shows his character.

'of' serves as the objective genitive, which follow verbal nouns.

Trying is a gerund; the verb phrase taking of the money serves as a noun, the subject of the main verb shows.

other examples include, "Bill's hatred/love/dreams etc., of (that specific) money..."

Also, do not confuse present particles with gerunds.

If its a participle, it can readily take an adverb:

Bill quickly taking the money, shows his (true) character.

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