repetitive "that"

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"Any question of whether Trump runs seem to have been answered this morning. His aides have always signaled that if the investigations progressed that he would run for president again."
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Hello to everybody.
Does the second "that" strike you as unnatural in this sentence?
 
It's not necessary. However, I would put commas around "if the investigations progressed".
 
I don't see anything wrong with the original sentence, but I suppose you could delete the second that.
 
Perhaps the versions below will show why the second that must be deleted.

His aides have always signaled that, if the investigations progressed, that he would run for president again."
His aides have always signaled that (if the investigations progressed) that he would run for president again.
His aides have always signaled that that he would run for president again, if the investigations progressed
 
I would delete the second that here, but that doesn't mean repetitive thats are always wrong- we can have two together:

He said that that policy was dreadful. ✅
He said that the policy was dreadful. ✅
 
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I think so too, it's apparantly a typical second conditional type, and you don't put a "that" between the if-clause and the result clause: "if the investigations progressed, that❌ he would run for president again."
 
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