A gambler places his bet without knowing the outcome and under the assumption that there is security behind the gamble, a false self-assurance that makes him a gambler for the thrill.
A chessmaster proceeds with an actual purpose, which it's implied when it comes to Littlefinger.
Littlefinger certainly knew what he was doing by inciting war between the Starks and the Lannisters.
The problem lies with the Chessmaster trope which equates the Chess as a metaphor for politics, when politics is quite uncertain/risky and random in many respects. So I don't see LF as more of a gambler than usual.
Littlefinger is both a Chessmaster, a gambler and plays Xanatos Speed Chess (which means that he is both ready and able to take a risk and make quick moves, while rolling with the punches). He is a gambler in a way that he gambles heavily during tourneys. But it is mostly just for the look of things, for show, to cultivate a certain image. Even when he gambles, whether he wins or loses, Littlefinger has already won by the fact that tourney is happening in King's Landing and he is earning a lot of money on prostitutes and eateries/ inns.
Personally i think Littlefinger has more in common with Heathcliff from Wuthering Heights than Jay Gatsby. Heathcliff is adopted by Cathrine Earnshaw's father Mr. Earnshaw and is sent to live in Wuthering Heights. Heathcliff falls in love with Cathy. She reciprocates but marries someone else with more money; Edgar Linton. Heathcliff leaves Wuthering Heights and gains a fortune through questionable means. When he returns he marries Edgar's sister who has feelings for him but never stops loving Cathy. Cathy is pregnant and dies during childbirth. The child survives and is also named Cathy. Heathcliff has a son with Edgar's sister called Linton then makes Cathy 2.0 marry his son out of spite.
Hasn't anyone else noticed that Littlefinger is more a gambler then an outright chessmaster.
Please allow me to introduce myself, I am a man of wealth and taste. Nice to meet you, hope you can guess my name. Hide / Show Replies