My father won the lottery..his natal chart has Jupiter, Pluto, and north node conjunct in 2nd house. His progressed chart at the time of winning put Neptune and Venus conjunct in the second house. Squared by the moon and trined by Uranus. Transits to his natal chart he has transiting Pluto zero degree square to his natal venus, Transiting Pluto just leaving his 5th house. And natal venus is in the third ruling the 5th house.
He had transiting Saturn opposing his sun, mercury, and neptune and transiting mars square his Saturn. Sun is ruler of his 2nd.
Hope that helps.
Oh I should say my dad is a twin they were born 11 min.s apart I believe I will have too look but my Aunt has Gem rising my father has Cancer rising, so makes her houses different of course..but 4 days after he won she did get 5 of the 6 numbers on the lotto.