I think NATO's assassination of Gaddafi was a disaster re: relationship with Russia
2011: "Putin blamed himself for letting Gaddafi go, for not playing a strong role behind the scenes" [0]
2012: US threatens military action in Syria: "red line"
2013: Russia gives refuge to Edward Snowden
2013: John Kerry gives Syria a week to destroy their chemical weapons. "(Syria) isn't about to do it and it can't be done". Lavrov immediately negotiates a non-military solution. [1]
2014: Direct Russian intervention following the overthrow of the Ukrainian government (cf Yugoslavia)
2015: Full-scale Russian military props up the Syrian government side in the Syrian civil war (cf Libya)
2016: Russia is accused of manipulating the US election
[0] http://www.nola.com/opinions/index.ssf/2017/04/obamas_red_li... [1] https://en.wikipedia.org/wiki/United_Nations_Security_Counci...