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There was a phrase, “surprise on the upside” with specific quotation marks in the Washington Post (June 9) article with a headline, “Trump says he’ll size up Kim Jong Un within the first minutes of summit," followed by the clause:

“Voicing optimism ahead of the summit, the president suggested the North Korean dictator will “surprise on the upside.”

I checked the meaning of “surprise on the upside” on both Oxford and Cambridge online dictionaries, neither of which doesn’t carry definitions of this phrase.

An answer in WordReference to the question on this phrase states:

“surprise on the upside” is a financial jargon and used to indicate a surprise (an unexpected result) which is positive rather than negative.”

GoogleN gram shows that the phrase started to be in use in /around 1980. The usage went up to 0.00000004% level in 1990, and plummeted to 0.000000015% level, which seems to be almost a negligible currency to me.

Does “surprise on the upside” mean unexpectedly positive outcome? Is it really a technical (financial) jargon? Can I use it in daily conversation simply for 'very good news' ?

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    Sorry, but I disagree with that WordReference thing. On the upside and on the downside are idioms in English. On the upside means: when the pros of a thing are considered. On the downside means: when the cons of a things are considered. He will surprise on the upside means: He will surprise us when the pros of the meeting are considered. On the upside and downside are used all the time. That use of it with surprise is not an idiom. – Lambie Jun 9 '18 at 23:00
  • "Upside" and "downside" are idioms mostly relating to the financial markets. Trump's use of the term in this context is a hair confusing, as the term is usually used in reference to risks, and "upside risk" implies some unforeseen danger if the market rises or a company's financial situation improves or some such. – Hot Licks Jun 10 '18 at 0:09
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    But Googling "surprise on the upside" I see it's a common financial phrase, and apparently simply means "perform surprisingly well". – Hot Licks Jun 10 '18 at 0:14
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surprise on the upside TFD

Considering the positive, beneficial, advantageous, etc., aspects of a situation, especially one that is or would be otherwise negative, detrimental, or disadvantageous.

Hoping for the best in the case of K. Korea, a positive outcome could be a pleasant surprise. It cannot get worse. In financial terms though, many companies earnings can go counter to expectations and the surprise can be to the up or downside.

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