I guess the logic is that some of Nate's strategies helped Richmond get promoted right after relegation which is unheard of (as they even called it Nate's false nine). With how little Rupert probably thinks of Richmond it makes sense that he would be impressed by Nate's work there enough to take him on. The other factor being how much he probably wants to stick it to Rebecca, Ted and Richmond. Putting Nate in is a head game he would enjoy playing with Ted.
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