ランスキーとキューバの関わりは、「アメリカ大陸のモンテカルロ」としてハバナが人気を博していた1950年代、ハバナで多くのカジノ事業を成功させたことによる。また、ハバナを代表するアールデコ調のホテル「ハバナ・リビエラ」の開発など、さまざまなリゾート開発で手腕を発揮し、後に『ゴッドファーザー PART II』（1974年）で描かれた最新鋭のカジノを備えた。ハバナ滞在中に莫大な富を築いたと言われるランスキーだが、ハバナ時代に築いた資産の総額は誰も知る由もない。

Lansky’s association with Cuba came in the 1950s, at the height of Havana’s popularity as the “Monte Carlo of the Americas,” when he built many successful casino businesses in Havana. He also demonstrated his skills in various resort developments, including the development of one of the most iconic art-deco hotels in Havana known as “Havana Riviera” which had a state of the art casino that was later depicted in The Godfather Part II” (1974). While Lansky was in Havana, he said to have realized enormous wealth, but no one ever came to know the total amount of his assets that he amassed during his Havana years.