This may be a hot and unexpected take from me but it was appropriate in 2000 to take a pragmatic but firm and principled approach to Putin to see what could be accomplished. And in some ways this happened, Putin did attempt to make a half-hearted pivot West and position Russia as a GWOT partner and we did get stuff out of it. A lot of people forget how key the Russia facilitated Northern Distribution Network was to sustaining operations in Afghanistan all the way through the mid-teens. It was never on the table for him to be a democrat.
What happened is that we fell down on the “pragmatic and firm” part in a lot of ways and Putin cannily exploited us by trying to make everything purely an issue of pragmatism. We also scored some own goals by blundering into foreign adventures where Russia could make itself either helpful or harmful at relatively low cost (Afghanistan, Iraq, and Iraq fallout). But even worse we had a bipartisan series of leaders who allowed him to do what he does everywhere: turn Russia relations into a political issue instead of a national security issue.
Russia and how the United States relates to it have been important campaign issues since 2012, with the GOP and Dems switching sides based on how Putin wanted them to. And even before that, we had the very stupid and political reset button whipped out by HRC for a photo-op with Lavrov; thus forcing Obama into either an admission of failure or to keep fucking the chicken long past the point of enjoyment. This was an own goal long after GWB came around to McCain’s view; and then in 2012 you had Obama gleefully pretending like Russia was still a potential partner.
This is all incredibly stupid. Russia should never be an issue in American elections; Russia is a solved but difficult problem that we keep trying to find different solutions for. Only Putin wins when Russia takes up this much oxygen in internal political discussions and its truly a grand strategic masterclass that he has put on by keeping a declining and brittle Russia on the front burner.