Dreidel seems to be a pleasant, fun-filled and seemingly inconsequential game, reminding us about how the Jews hid in caves to study Torah, playing games at the mouth of the cave to scout for Greek Army troops, right? Yes, for sure. The Bnai Yissoschar adds, however, that those four letters on the Dreidel--Gimel, Shin, Nun and Heh are actually very lofty--for they together have a gematria, a numerical equivalent, of 358--which is also the gematria of Moshiach(!), and also of “Hashem Melech Hashem Malach Hashem Yimloch”--Hashem is, was and will be King. For Torah Jewry, there is profound depth and meaning infused even into what to the world is just fun and games!

Taking this thought a step further...

As we just explained, The four letters--Gimmel, Shin, Nun, Hey add up to 358--which is, of course, the Gematria of Moshiach!
​HaRav Fischel Schachter, Shlita, explains that the Gematria of Satan is 359--which would at first glance indicate that he would have the upper hand. However--by our taking the Dreidel into our hand--by our taking action--we add on five for our five fingers to the Gematria of Moshiach--overcoming the Satan and bring the Yeshuah!r Gematria of the Dreidel Letters