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In In the Midst of Alarms (1894) by Robert Barr, Yates was talking to his old friend about another old friend that had caused Yates to be expelled from the academy:

But what I detested was the way the principal worked the thing. He allowed that villain Spink to turn evidence against us, and Spink stated I originated the affair, whereas I could claim no such honor. It was Spink’s own project, which I fell in with, as I did with every disreputable thing proposed. Of course the principal believed at once that I was the chief criminal. Do you happen to know if Spink has been hanged yet?”

“I believe he is a very reputable business man in Montreal, and much respected.”

“I might have suspected that. Well, you keep your eye on the respected Spink. If he doesn’t fail some day, and make a lot of money, I’m a Dutchman.

  1. How can he "fail while making a lot of money"?

  2. Does "might have suspected" = "perhaps I should have guessed"?

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To the first question: the intended meaning is indeed "fail + make a lot of money". Yates is not a Dutchman, so he is saying that he expects Spink (a) to "fail" and (b) to make a lot of money. How that might work is illustrated by the example of Brown, who had also been expelled from the academy, just like Yates. Yates says to Renmark,

Well, Brown, by his own exertions, became president of the Alum Bank in New York, wrecked it, and got off to Canada with a clear half million. Yes, sir. I saw him in Quebec not six months ago. Keeps the finest span and carriage in the city, and lives in a palace.

Yates has a similarly low opinion of Spink and expects him to do something similar, which is why he asks Renmark whether he has been hanged yet and later adds, "you keep your eye on the respected Spink" (in which "respected" is presumably spoken in an ironic tone). His low esteem of Spink is a consequence of being expelled from the academy because evidence from Spink that got Yates expelled from "Scragmore's academy".

To the second question: your interpretation is basically correct. It is something Yates could have expected (hypothetically) but apparently didn't.

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    Many thanks, but shouldn't have he said "if he fails, then I'm a dutchman" to show that he will not fail? – Ahmed Samir Feb 28 at 9:18
  • So, it simply means "if he doesn't fail and doesn't make a lot of money", I'm a Dutchman, because he evidently don't like him, and even thought that he had been hanged! – Ahmed Samir Feb 28 at 12:20
  • Thank you so much, yet it's still a bit obscure for me, because I can't capture his opinion of Spink: Did he expect that he should have been hanged, or should have suspected that he has became a very successful businessman? – Ahmed Samir Feb 28 at 12:29
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    Since Spink had lied during the "affair" at the academy, which had led to Yates's expulsion, Yates had either hoped or expected that the man would not end up well. ("Hoped" if he had wanted some sort of vengeance, or "expected" because his lies would cause serious problems some day.) Based on what Renmark tells him, Yates realises that Spink is smart enough to be successful financially. – Tsundoku Feb 28 at 12:48
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    Thanks for pointing that out. Based on that, I have completely rewritten my answer! – Tsundoku Feb 28 at 15:08

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