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Reading "Trumpery - A Twitter meme caused lookups to spike" on M-W got me wondering about Trump and Trumpery. I meant about the words itself and not about candidate Donald Trump's qualities.

Trump

a dependable and exemplary person

Trumpery

worthless nonsense

How did they develop such opposing meanings?

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    Etymonline's entry for trump just about covers it. The difference between sense 1 and sense 2 (which is the sense the entry for trumpery defers to) on that page corresponds to the difference you noticed between trump and trumpery. And explanation / history is given for both exemplary (i.e. trump) and deceitful (i.e. trumpery). The ultimate origins are murky, but interestingly both trace back to the instrument (and the onomatopoeia for the instrument).
    – Dan Bron
    Mar 4, 2016 at 16:30
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    Just a guess: trumpery from French tromper - to deceive?
    – David Garner
    Mar 4, 2016 at 16:31
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    @DanBron Add to that, the fact that in Britain, trump has, since the sixteenth-century, been a euphemism for breaking wind, and the poor (sic) man does carry an unfortunate surname for a possible presidential candidate.
    – WS2
    Mar 4, 2016 at 16:32

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The Merriam-Webster pages that you link to actually give the etymologies of the two words (though I don't blame you for missing it; the Merriam-Webster page structure is a bit hard to follow).

According to those pages, trump is an

alteration of 1triumph

whereas

Trumpery derives from the Middle English trompery and ultimately from the Middle French tromper, meaning "to deceive." […]

so they're actually unrelated, and the similarity of appearance is coincidental.

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