Donald Trump celebrated Cinco De Mayo last week with a meal decidedly outside of traditional Mexican cuisine, and a Twitter message that many found wince-worthy — especially considering his labeling of Mexican immigrants as “rapists” early in his presidential campaign.

Happy #CincoDeMayo! The best taco bowls are made in Trump Tower Grill. I love Hispanics! https://t.co/ufoTeQd8yA pic.twitter.com/k01Mc6CuDI

— Donald J. Trump (@realDonaldTrump) May 5, 2016

Trump has unprecedented low popularity with Latinos, likely due to the aforementioned “rapists” comment, and for his twin promises to begin mass deportations of immigrants and to build a giant wall along the U.S.-Mexico border. But he isn’t the first U.S. politician to stumble when attempting to reach out to Latino voters.  

Brent Wilkes, the national executive director of the League of United Latin American Citizens said in an email that cultural outreach wasn’t enough.

“Serious candidates running for our country’s highest office understand that 
in order to win the Latino vote they must address issues that matter to 
Latinos, such as the need for comprehensive immigration reform, and improved 
educational opportunities for all. Disingenuous attempts to relate to 
Latinos only serve to expose a cultural ignorance that will alienate the 
Latino community,” Wilkes said. 

Gerald Ford learns about Mexican food

In fight for the ’76 nomination, President Ford ate a tamale w the husk on. Furthered his (unreserved) rep as klutz. pic.twitter.com/2gsdPBDBZt

— R Juarez (@GovJuarez) April 26, 2016

Ford also wore a sombrero in the White House — a hat he’d received on a presidential visit to Mexico.

#NotMyAbuela

Abuelita mexican chocolate now available in white chocolate #HillaryClinton #notmyabuela pic.twitter.com/UiZMxjU1TX

— David del 956. (@bombassdave) January 17, 2016

In a Buzzfeed-style article, “Seven things Hillary Clinton has in common with your Abuela ,” the Clinton campaign tried to make the case in December that the Democratic front-runner was just like a Latina grandmother. It backfired spectacularly, with many seeing the effort as pandering. It was immediately met with a torrent of mockery on social media, under the hashtag #NotMyAbuela.

(1/4) To get the #latinovote @HillaryClinton was “just like your Abuela” #hispandering #notmyabuela

— Shayma (@ShaymaHadid) April 20, 2016

The hashtag has been used since then to tag any Clinton effort seen as pandering, including when she played dominoes in the Bronx in the lead-up to the New York primary.

Seriously .@HillaryClinton that’s another example why your #notmyabuela #hillaryfails pic.twitter.com/PmTN3BBFEO

— Fernando A Quezada (@FernandoAQuezad) April 19, 2016

In Texas, Clinton also tested out the lines  “La Hillary” and “Tu Hillary” (“The Hillary” and “Your Hillary” in Spanish), which garnered a similarly uncomfortable reaction from some voters.

Rick Santorum makes up English-only law

In March of 2012, Rick Santorum traveled to Puerto Rico to campaign ahead of the island’s Republican primary. Instead he managed to lob an insult at Puerto Ricans and invent a federal law in an interview with the self-governing U.S. commonwealth’s El Vocero newspaper.

“Like any other state, there has to be compliance with this and any other federal law. And that is that English has to be the principal language. There are other states with more than one language such as Hawaii but to be a state of the United States, English has to be the principal language.”

Both English and Spanish are official languages in Puerto Rico, and no law exists that would require a new state to declare English as an official language. In fact no federal law gives English any precedence as a national language over any other language.  

Santorum placed second with 8 percent of the vote in the Puerto Rico primary, to Mitt Romney’s 80 percent.

Mitt Romney loves Che

Mitt Romney thought he was quoting anti-Castro dissidents when he delivered this line to Latino Republicans in 2007.

“Hugo Chavez has tried to steal an inspiring phrase — ‘Patria o muerte, venceremos.’ It does not belong to him. It belongs to a free Cuba.”

In fact, the line — which means “Fatherland or death, we shall overcome” in Spanish — was made famous by Che Guevara, the communist revolutionary and major figure in the Cuban Revolution that brought Fidel Castro to power.

Romney would rather be Latino

Romney managed to land himself in hot water with Latinos again in his second presidential campaign. In 2012, in the same secretly recorded video that exposed his assertion that 47 percent of Americans were so dependent on government largesse they’d vote for Obama no matter what, he also made a less-noticed joke .  

He lamented the fact that his father was born to “Americans living in Mexico,” rather than “Mexican parents”.

“I say that jokingly, but it would be helpful to be Latino.”

George H. W. Bush and the “little brown ones”

In 1988, Vice President George H. W. Bush earned some ire from the Mexican-American Political Association when he described his son Jeb’s 3 children with his Mexican-born wife Columba as “the little brown ones.” Bush defended his choice of words, saying his heart knows nothing but “pride and love” for the children.  

“Just saying that means he knows they’re different. He didn’t say, ‘Those are my grandchildren.’ He didn’t just refer to the kids by their names,” said Al Belmontez, then a vice president of one of the association’s local chapters. “That just shows that he’s … insensitive.”  

Get breaking news alerts and more from Roll Call on your iPhone or your Android.