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His aides reassured him that he still would have won had he been able to run for another term and that the next generation had more in common with him than with Mr. Trump.

How Trump’s Election Shook Obama: ‘What if We Were Wrong?’

Can Obama run another term (Like Putin) after Trump? Or Just a joke?

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    If you replace "had" with "if" would it make more sense to you? – Catija May 31 '18 at 1:57
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    As @Catija states, the sentence could be "His aides reassured him that he still would have won if he had been able to run for another term and that the next generation had more in common with him than with Mr. Trump." – holydragon May 31 '18 at 2:06
  • @Catija, Yes, Great! – Zhang May 31 '18 at 2:08
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Two questions there, second one first:

No, Obama could not run again, he was term limited to two terms.

First question: What does "would have won had" mean in this sentence?

Answer: It's setting up a hypothetical with an implied if. Let me reword it this way: "If President Obama had not been term limited, he would have been able to run again. In this hypothetical scenario, the polling indicated he would have won against Mr. Trump."

The "would have" is the "hypothetical case": "would have won (if)" gives the result of the hypothetical case and the "had" leads off the conditional for the hypothetical: "had he been able to run".

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