This question was asked by Kt Boehrer, astrologer, on November 9, 2000, at 5:46:48 PM EST, in Arlington, Virginia, USA.
This is an interesting question, quite hard to analyse correctly previous to its outcome.
George W. Bush is represented by the 7th house ruler Jupiter.
His chances to become President are shown in the turned 10th house from the 7th, that is the radix 4th house, ruled by the Sun.
We're looking for an classical ptolemaic aspect between these two significators, to show him winning the elections, but there is none.
However, there is a connection by antiscia ! This is a quite subtle connection between the significators, "by shadow" (antiscia), therefore in an obscure, hidden way: the Sun at 17°50' Scorpion is in applying trine with Jupiter's antiscion at 21°29' Cancer.
The horary chart depicts the whole situation quite clearly: the Sun is in the same degree as the nodes (critical situation for this election) in his turned 12th house and Scorpio (weird stuff). Mars (ruler of radix 12th house) applies by trine to Jupiter = he's being helped by some unknown/secret persons. The Moon is applying by trine to Venus (ruler of the turned 12th house), then by square to Lilith (at 28°16' Capricorn, not shown in the chart, this is highly revealing for fraud!) and finally by trine to the Part of Fortune (he gets the Presidency).