Donald Trump’s affront against the Latino community reached new heights last week after Mexican-American journalist Jorge Ramos was forcibly removed from the presidential candidate’s Iowa press conference. But it wasn’t the first time Trump has offended Latinos.

His anti-Latino remarks have cost him several business partners since the launch of his campaign in June, including NBCUniversal, which aired Trump’s reality show “The Apprentice” and co-owns the Miss Universe Organization. Several prominent figures in the Latino community have also spoken out against Trump; actress America Ferrera and singer Ricky Martin published scathing op-eds condemning Trump’s actions and rallying Latinos to unite against him.

Even though only 18 percent of Hispanics take Trump seriously as a presidential candidate, the Republican has vowed that he “will win the Latino vote” if nominated.

If Trump wants to win the Latino vote, he might want to learn from past mistakes. Here are 9 of the most outrageous things the presidential candidate has said about Latinos.

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