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I was always told that the former order is the only grammatical one, however, in one of the videos on Youtube (https://youtu.be/qXXZLoq2zFc?t=7m6s) I encountered the latter order:

"The only winning move is to not play"

instead of

"The only winning move is not to play"

Can this order be used in some instances? When can you do this? What is the meaning of such order?

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tobruk, either structure is grammatically acceptable and expresses the same meaning: in both cases, the action is negated. Your first rendering negates the infinitive "to play"; your second rendering negates the verb "play". You may be a victim of the imposition of an entirely silly "rule" about split infinitives. In English, a split infinitive occurs when a word intervenes between the to and the verb of an infinitive (as in "to not play"). Beginning in the early 1900s, some prescriptive grammarians decided that, because Latin infinitives were never split, English infinitives should also never be split. This rule is silly for two reasons: First, Latin infinitives are always single words (unlike the English two-word structure), so Latin infinitives can't be split. Second, English speakers have been splitting infinitives since at least Old English times (see the Beowulf poem for some hearty examples), with split infinitives the preferred structure when adverbs modify the infinitives. Perhaps the most famous split infinitive of modern times appears in the opening monologue of Star Trek, when Captain Kirk says that the mission of the Starship Enterprise is "to boldly go where no man has gone before". This resonant phrase would limp badly if it were revised "boldly to go" or "to go boldly". Bottom line, take it as your mission to boldly split infinitives to your heart's content. Lune

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  • I would say that there is a difference. In the case of "not to play" one merely refrains or omits to play, possibly even by mistake: in the case of "to not play" one has made a very definite decision to avoid playing. If the sentences refer to gambling then the first might refer to a player passing on a turn, the second could relate to a principled refusal to gamble.The difference is that the 'not' negates the verb 'to play' in the first case but in the second the 'not' becomes part of a compound verb 'to not play'. This is a personal opinion but I believe it to be correct.
    – BoldBen
    Commented Jan 23, 2018 at 0:13
  • BoldBen, the word "not" is an adverb of frequency, and as such it never becomes coupled with a verb to form a compound verb (nor do any other adverbs). Compound verbs (relatively rare in English) emerge only from the compounding of verbs with verbs or of verbs with nouns (never with adverbs). The semantic meaning of the two phrasings are identical, so a choice between them is purely stylistic. To my ear, "not to play" expresses more of a willful stress ("I choose not to play his silly games."). Lune
    – LuneKeltkar
    Commented Jan 23, 2018 at 0:28
  • I would dearly love to see supposed split infinitives in Old English or any other Germanic language, or, for that matter, any concern with split infinitives in English before the latter half of the 19th century. merriam-webster.com/words-at-play/to-boldly-split-infinitives
    – KarlG
    Commented Jan 23, 2018 at 1:14
  • As the inflectional case system of Old English began to transmogrify into an analytic grammar (still imperfectly realized), the Old English one-word infinitive shifted onto the current to + verb structure (not consistently realized until Middle English times). You'll find this developing infinitive structure in the Beowulf poem and in some of Alfred's writings. You might study these works for the examples that you would dearly love to see. (more to follow) Lune
    – LuneKeltkar
    Commented Jan 23, 2018 at 10:56
  • For split infinitives in Germanic languages, study any of the Scandinavian languages (German, not so much). As for the history of the prescriptive rule against splitting English infinitives, the rule found its efflorescence in the latter half of the nineteenth century, but this flourishing came at the end of at least a half-century of growing fulminations against split infinitives. Even your cited source points out that an early diatribe appeared in an 1803 publication. Lune
    – LuneKeltkar
    Commented Jan 23, 2018 at 10:57

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