Learn English – “armchair analysis sound”

I've never heard this phrase before, but what it sounds like the speaker is trying to say is that they've never before done whatever "it" refers to. For example if you said "The last time I did [x] was 2002," you'd be stating the last time you did it. "two thousand-never" (instead of "two thousand-two") seems to be a funny way of saying you've never done something. So I'd say the sentence probably has identical meaning if you just remove the "2000-" and say "The last time I did [x] was never."

Now note that this isn't grammatically correct; you can't actually say "The last time I did [x] was never." The correct thing to say would be "I have never done [x]". But the joke still stands, I think.

"CNN's Christiane Amanpour asked Russian Foreign Minister Sergey Lavrov in an interview to comment on the state of the U.S. presidential election. She ended up getting a bit more than she bargained for when she prefaced the question with a reference to the Russian punk band 'Pussy Riot.' Short transcript of the exchange: AMANPOUR: Can I just try one last question? One last question. A bit cheeky but I'm going to ask you. Russia had its own Pussy Riot moment. What do you think of Donald Trump’s pussy riot moment?

"LAVROV: Well, I don't know what this would… English is not my mother tongue, I don't know if I would sound decent. There are so many pussies around the presidential campaign on both sides that I prefer not to comment on this. read more: http://www.haaretz.com/world-news/u-s-election-2016/1.747244"

"Seeing the transcript, I can now address it more clearly. Amanpour is making a play on words. Russia had an incident involving the band Pussy Riot: a literal "Pussy Riot" moment. Donald Trump also recently had an incident involving the word "pussy", which caused a great uproar: a metaphorical "riot about the word 'pussy'" moment."

(All credit for this analysis goes to @stangdon with my thanks.)