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If there is one area in which Donald Trump succeeds, it’s coming up with controversial things to say.

Trump’s recent inflammatory comments about Mexican immigrants were not the only insensitive remarks he’s ever made in an attempt to generate attention. The entrepreneur has a long and storied history of flapping his lips before using his curiously-coiffed noggin.

Here are some of his more offensive remarks, in no particular order (except for maybe that last one).

1. “The U.S. has become a dumping ground for everybody else’s problems. When Mexico sends its people, they’re not sending their best. They’re not sending you. They’re sending people that have lots of problems, and they’re bringing those problems with us. They’re bringing drugs. They’re bringing crime. They’re rapists. And some, I assume, are good people.” — June 16, 2015

2. “I’ve read hundreds of books about China over the decades. I know the Chinese. I’ve made a lot of money with the Chinese. I understand the Chinese mind.” — May 2011

3. “Sadly, because president Obama has done such a poor job as president, you won’t see another black president for generations!” — Nov. 25, 2014

4. “I have people that have been studying [Obama’s birth certificate] and they cannot believe what they’re finding… I would like to have him show his birth certificate, and can I be honest with you, I hope he can. Because if he can’t, if he can’t, if he wasn’t born in this country, which is a real possibility…then he has pulled one of the great cons in the history of politics.” — April 7, 2011

5. “All of the women on The Apprentice flirted with me — consciously or unconsciously. That’s good to be expected.” — March 24, 2004

6. “I have a great relationship with the blacks.” — April 14, 2011

7. “While @BetteMidler is an extremely unattractive woman, I refuse to say that because I always insist on being politically correct.” — Oct. 28, 2012

8. “I think the only difference between me and the other candidates is that I’m more honest and my women are more beautiful.” — 1999

9. “It’s Friday. How many bald eagles did wind turbines kill today? They are an environmental & aesthetic disaster.” — Aug. 24, 2012

10. “I am officially running for the President of the United States.” — June 16, 2015