Frontline did a good piece on Putin a while back. Putin played both Bush Jr (with the "grandmother's crucifix"), and Trump. He didn't know how to handle Obama (in large part because he was black, and he couldn't understand how we would elect a black man). Plus the VP (Biden) and Putin actively disliked each other (Biden was on the Senate Foreign Relations committee). Biden becoming POTUS was not in his plans. Biden was an old cold warrior, like Putin.

Putin's worst nightmare is a POTUS/Congress that will continue support for Ukraine. That means his armed forces will be mired in Ukraine for at least another 4 years, when he was expecting a victory in less than 4 months (back in 2022). Harris will have decent advisers, and keep Putin busy for years. Putin already has pushed two new members into NATO, his navy has suffered several significant losses, his army has suffered grievous casualties, his stockpiles are dwindling (e.g. they've pulled T62 tanks out of mothballs because he can't make enough new tanks...those are Vietnam era), etc.

Vlad has dreams of reestablishing the USSR, and the convict would help him greatly in that task, due to his easy manipulation. Vlad's own actions have been disastrous for those plans. If the US continues support for Ukraine, along with European support, Putin will be tied up for a decade or more. He won't have the resources to meddle elsewhere, nor the economy to support it, while strengthening alliances against him.