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There was the following sentence in the article titled, “Vegas. Rove attack ads seal victory for Hillary” appearing in May 10 New Yorker magazine:

“The oddsmaker’s only concern, he added, was that Rove’s involvement in the race will dry up all interest in betting on Republican candidates for 2016: “Right now I’m offering Marco Rubio at ninety thousand to one and I ain’t getting a bite.”

While acknowledging that “there’s no sure thing” in the world of gambling, Mr. Klugian said that for professional gamblers, betting against Karl Rove is “as good as it gets.” “He’s the LeBron James of losing,” he said.”

I understand this is simply a metaphoric joke, and I understand clearly what the oddmaker means.

But “the LeBron James of losing” sounds somewhat farfetching just as saying “the Babe Ruth of losing” and “the Great Alexander of losing” instead of "Darius III of losing"?

Doesn’t this contradiction – ‘the ever-victorious of losing’ - matter?

Does the expression, someone like “the LeBron James of losing,” sound natural and reasonable to native English speakers, simply from the view point of rhetoric and logic?

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Yes, this sounds natural to me. LeBron James has been nicknamed "King James" & is some sort of star basketball player (I don't follow the sporting news, but I've heard the name). The metaphor is culture-bound. It's always better to be specific when one makes comparisons. Being vague and general is boring and often unclear.

Your translation (from English to English) of "the LeBron James of losing" is incorrect. It's as possible to be the king of a rich and powerful country that wins all its wars as to be the king of a poor and weak country that loses all its wars.

All the metaphor means is that Rove is the #1 political loser in the USA, not 'the ever-victorious of losing'.

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