The music mogul wishes US network Fox had understood why he pushed for his fellow British judge to join the panel on the new American show and doesn't feel the singer realised how hard he fought for her to remain with the programme before she was axed after just four auditions.
Simon's close friend Sinitta said: "Although people see Cheryl more as the injured party, Simon's hurt too. He's hurt that she hasn't appreciated or understood how hard he fought for her.
"He's hurt because he knows that he really stuck his neck out for her. As much as it's been a disappointment for her that it didn't work out, it's a disappointment for me too, because it reflects on his judgement and his ability to know what people out there want."
Sinitta claims Simon feels "helpless" over the situation at the moment but is hopeful it won't ruin his friendship with Cheryl.
She added: "He is definitely rattled, but I also know that he did his best and, for a man, there's nothing worse than feeling helpless.
"Feelings are running so high right now but I sincerely hope they can emerge from all this as friends."
Cheryl was axed from the US show after filming four auditions and then turned down a double-pay offer to return to the UK 'X Factor'.
She was then offered the Stateside job back but declined, and has been replaced on the panel by Nicole Scherzinger.
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