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Longest

Longest[p] tries the longest split of a sequence pattern first; the default is the shortest, which is what Shortest[p] asks for explicitly.

$ wo '{1, 2, 3} /. {Longest[x__], y__} :> {{x}, {y}}'
{{1, 2}, {3}}

$ wo '{1, 2, 3} /. {Shortest[x__], y__} :> {{x}, {y}}'
{{1}, {2, 3}}

Around anything that is not a sequence the wrapper is transparent:

$ wo '{{1, 2, 3} /. {Longest[x_], ___} :> x, MatchQ[{1, 2}, {Longest[__], _}]}'
{1, True}