The gambling idea came about during the time of the Greeks. Jews were thought to be lazy and nothing but gamblers so this became a way to fool the soldiers. Since Jews were forbidden to come together and study or pray but somehow gambling was acceptable, that is what they did. When the guards weren’t paying attention, our ancestors could study Torah. The game was an immediate cover. Sometime during the medieval period the dreidel was introduced. At some point it overtook other game forms during Hanukkah and today remains an icon for the festival.
This is idea is uncertain and came about after the fact and still holds controversy.
Regardless of the origin, it’s mnemonic device stands for “A great miracle happened there (here)”. Every time the dreidel is touched, the players are reminded of the events which gave way to holiday. A time of perseverance and of hope and of victory. I guess I also wonder if during the miracle, those involved know it was so. What I mean is that I can’t imagine the Macabees coming to the
But a miracle? They just suffered the destruction of the holiest places they knew and some oil burning longer than expected would elicit the response of miracle? This could be the cynic in me talking or it could be the cliché regarding the clarity of hindsight. I actually like to think that they weren’t really aware of what was in front of them. I am then able to look at my life and the lives of those around me and wonder if this too is a miracle. I contrast this idea of miracle with the parting of the
The little miracles are as entrenched in our history as the big ones. I find this thought to give great comfort in my life and I am able to find appreciation in the most minute things when viewed this way.
For an explanation on why gambling is encouraged during Hanukkah even though the rest of the year it's frowned upon, see this post from hagshama.
Chabad (again I'll save my personal opinions for another time; they have a great website as usual though) has some insight with Kabbalah and Gematria here.

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