Now that Mueller has moved directly against Russians interfering in the 2016 election, the interesting question isn’t why Putin wanted Trump to win – he was probably as surprised as anyone that Trump actually made it – but what was his beef with Hillary. She was singled out as the bulls’eye target. Observers said Putin was personally insulted when Hillary supported protesters in Moscow accusing Putin of having rigged the 2011 election. He suggested she had fomented the demonstrations to undermine his power. He said “We need to safeguard ourselves from this interference in our internal affairs.” So part payback. She had also been on the hawkish end as Secretary of State, sending defensive weapons to Ukraine; was a staunch supporter of NATO, a staunch supporter of the sanctions [against Russia], and criticized Putin’s annexation of Crimea.
Their charts certainly clash. Putin’s Mars opposes Hillary’s Uranus, trines her Saturn and squares her Pisces Moon, for an explosive and aggravated chemistry; both have determined Venus in Scorpio.
Their relationship chart has a composite Sun Mars Neptune – argumentative, competitive, not mutually supportive (only one can win) with a oneupmanship, power-struggling Pluto opposition Jupiter. That relationship has always been bad but will worsen considerably over the next three years – with tr Pluto square the composite Mars now, and moving to square Sun/Mars and then the Sun in 2019/2020.
Putin’s other aim would be to cause chaos, putting the USA off balance and therefore less likely to be interfering in Russian interests. His Uranus is conjunct the US’s Sun and square the US’s Saturn – so a ratchety interface. With his formidably determined and ruthless Mars (trine Pluto) square the US Neptune. That relationship looks downbeat at the moment and through this year; with challenges and frustrations in 2019/2020; and a re-set only coming from 2021 onwards.
My take is that he is an authoritarian and likes other authoritarian leaders, hence his support also for Erdogan in Turkey and the le Pen’s in France as well as Assad.