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I saw the following sentence in today's New York Times:

Despite questions about their coach's outsize personality, the Jets have won three playoff games in two seasons under Rex Ryan.

As the expression 'outsize personality' is quite new to me, I consulted Google and found the following example containing it:

Obregón, Alejandro’s work was widely exhibited in Latin America and elsewhere and in 1956 he won first prize at the Guggenheim International Exhibition in New York. Edward Lucie-Smith described him as ‘an outsize personality'…

Does 'outsize personality' mean outspoken, carefree character? Does it sound positive or negative to the person when he or she was characterized so? What does it mean exactly?

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Something that is outsize (or outsized) is exceptionally large. If used to describe someone's personality, it may mean "larger than life" or flamboyant. It can be positive, but it can also be negative.

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    We use to have a guy around us who is always hilariou and talk big, a kind of big dreamer whom we nicknamed a 'Gokurakucho - paradise bird' in Japanese. Maybe that sort of person? Yoichi – Yoichi Oishi Jan 11 '11 at 2:21
  • 極楽鳥?あの人知ってると思う。。。 – Robusto Jan 11 '11 at 4:13
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It means the same as 'larger than life', which is to say someone that stands out more than the average bear.

Usual characteristics would be as you describe, outspokenness, noticeable character, either in a jubilant happy way or sometimes in a gruff and loud manner. Usually the sort of person that within a group is the one that tends to be making the boldest statements or acting in a way that draws the most attention.

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