I’ve never heard it, but then again, I am not fluent in racist.
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I just hope DeSantis does not try the ‘no monkey, no monkey, you are a monkey!’ defense.
Miiiiiiiiiiiiiight backfire here.
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I believe that or a similar phrase may have occurred in a Three Stooges episode. Because they needed a huge vocabulary of insults for each other.
See my comment in this thread about referring to a stupid chicken, and of course someone replying “or a monkey.”
You know someone is a … when monkey references come up as their first thing.
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I’ve heard “don’t muck it up”.
It was either a deliberate slip or Desantis had “monkey” on his mind when thinking of Gillum.
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Good luck, Miami, getting Amazon HQ 2
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That settles it pretty good.
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https://www.merriam-webster.com/dictionary/monkey%20wrench
But in context the term woukd be avoided by anyone not seeking to send racist dog whistles.
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Mr DeSantis, it is anything but absurd. In this case the “anything” is racist. It cannot be interpreted any other way. Your “logic” is the same as saying it isn’t dark out at night. Or that the Sun doesn’t shine during the day.
And DeSantis is trying to see how many times he can fit “Gillum” and “monkey” into the same sentence by the end of the day.
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I have heard this usage (nonracially). It’s even sort of logical. But then I’m not so young, so it’s probably long fallen out of use. But now it may be the new “macaca” - let’s hope. (see George Allen (American politician) - Wikipedia)
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In a database of 50 major newspapers, including the NYT, WSJ and WaPo, I got zero hits from before today on “monkey this up.” This is an archive (Factiva) that goes back decades for many of the papers.
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One running for office should not use words like “monkey” when referring to one’s opponent when that opponent is African American. But this is today’s GOP. Civility is for losers these days.
In other situations it’s ok … like monkey wrench for example.
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Whats absurd is this candidate defending the indefensible. I’m with MattinPa, this phrase makes no sense and I’ve never ever heard it used. When you realize this guy’s opponent is black, there is only ONE meaning of this phrase. It is ONLY a racist meaning, there is no other meaning. 
AWESOME. Can I have shirts printed up with this on them?? Hilarious…
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Monkey-wrenching is deliberate sabotage. The thing is, politicians above the state-rep level learn to talk in public very, very carefully. He said “monkey” because he wanted to. The chance of a serious politico making that mistake innocently while talking about a black person gets pretty close to zero. Let’s just not even waste our effort here.
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I’m beyond the ‘is this a racist thing to say’ debate (there really is no debate). Now I’m in the phase of asking…‘who the hell talks this way?’ Seriously. Who? Are we in 2018 or 1818? WTF!!!
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I’m sure there are very fine people on both sides of this racist slur.
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The Florida State Dog Whistle Ensemble is warming up.
There was a time when monkey business like this was a firing offense.
Of course, that was West Virginia, which has a considerably lower tolerance for racism than Florida.
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I have heard iterations of “monkey it up” about a million times, in non-racist context. It’s a southern expression, which might have historical racist DNA invisible to old, white, southern men. (Like “cotton-picking” as in “I nearly broke my cotton-picking neck!”) I’m not 100% certain it was an intentional dog whistle.