Gambling, anxiety about reality, and the wish to find a way of contolling chance, of experiencing it as part of a rational universe, or of playing with inner anxiety in order to control it are a strong feature of Pascal and Hume. Where would philosophy be without their interest in gambling?
Mention is made of Hume's talk of backgammon in Treatise 1.4.7, but one important instance of Hume's use of the trope of gambling is in Treatise 18.104.22.168:
If we want another parallel to these affections [involved in curiosity or love of truth], we may consider the passion of gaming, which affords a pleasure from the same principles as hunting and philosophy. It has been remark'd, that the pleasure of gaming arises not from interest alone; since many leave a sure gain for this entertainment: Neither is it deriv'd from the game alone; since the same persons have no satisfaction, when they play for nothing: But proceeds from both these causes united, tho' separately they have no effect. 'Tis here, as in certain chymical preparations, where the mixture of two clear and transparent liquids produce a third, which is opaque and colour'd.