LORELAI: It’s the title search for the Rachel property. And guess who owns it.
SOOKIE: Tell me it’s not that bastard Donald Trump.
Donald Trump (born 1946), American businessman, media personality, and politician. He became president of his father’s real estate business in 1971 and renamed it The Trump Organisation. Trump expanded the company’s operations to building and renovating skyscrapers, hotels, casinos, and golf courses. He later started various side ventures, mostly by licensing his name. Trump and his businesses have been involved in more than 4,000 state and federal legal actions, including six bankruptcies. He owned the Miss Universe brand of beauty pageants from 1996 to 2015.
Sookie seems to think of Donald Trump as someone who owns so much real estate, any random property could very well be his. Although it seems comically unlikely he would own a rundown inn in rural Connecticut, he did have a history of buying derelict hotels and doing them up.
It’s probably best that Sookie doesn’t know that Donald Trump will later become the President of the United States (2017-2021).