n. The qualities or characteristics that make a person a winner.
Why it's big if Cruz beats Trump, says Nicole Wallace on MSNBC: "His central BEING for being in this race is his WINNERLINESS…"
—Shinan Govani, “Why it's big…,” Twitter, February 01, 2016
And while Tebow is very good, his strengths are mostly to do with unquantifiable "intangibles" like "winnerliness" and "composure."
—TheElusiveKyleOverton, “Elway deal finalized, Harbaugh is #1 choice, per schefter” (reply), The Orange Mane, January 02, 2011
Fictive worlds are different, though: as I said above, their characters' worlds are not ours. Moreover, with fiction, especially contemporary fiction, we have no guarantees as to the winnerliness or loserliness of its characters.
—John B, “"Why read something made up . . . ?": On unknowableness in fiction,” Blog Meridian, October 21, 2007
2005 (earliest)
Believe me, there are many, many people out there who will try to stop you on your long and tiring journey to greatitude and winnerliness.
—blue car, “How To Win At Life,” Kuro5hin, July 04, 2005
For the candidates, a win in Iowa, or even a strong showing, will provide the increased press coverage that those now dwelling in crowded obscurity need. It will provide what is commonly referred to as momentum. The candidate who looks like a "winner" will get more money and other forms of help.

One's "winnerness" may be more important in the process than what one stands for.
—Elizabeth Drew, “A Reporter In Washington, D.C.,” The New Yorker, January 01, 1976
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