Regarding Bordeaux, would you rather have a second wine from a fantastic vintage (eg 2010) or the grand vin from a less heralded vintage such as 2013, 2007, or 2004?
I think there was a time when second wines had some value but it seems like those days have past us by, so I’ll take the lesser vintage.
I know it wasn’t your original question but, I’d rather buy the top wine from a lesser estate in the great year, every time
+1 to the bolded statement.
I’ve been enjoying some second wines lately such as comtesse de lalande, dame de Montrose, Josephine de Boyd… just a thought
I’d take Latour over Forts every time, the only wines I can think of that may apply to your rule are Croix de Beaucaillou or Dame Montrose where I may take the great vintage.
Is neither an option?
I’d rather have a wine like Pichon Lalande from a very solid vintage – like 2014.
Forced to choose between the two alternatives, I’d certainly take the first in most “less heralded vintages.” In every vintage, the first is “the best wine we can make.” The second wine is always “stuff left over after we’ve made the best wine we can make for someone else.” When they were cheap, they could be decent values. Don’t much consider them now.
However, I’d rather have a great wine regardless of vintage. And in nearly every vintage (including the ones you named) there are outstanding wines outside the first growths, and frankly I’d rather have 3 of them than one bottle of the first.
Hard to say generally- it depends!
I would always take a Dame de Montrose 1990 or 2010 instead of a 1991 or 2011 or 2013 Montrose … or 2010 Forts de Latour for 2013 Latour …
some more examples … but usually I´d prefer the Grand Vin … some 2nd wines are really not immensly interesting!
If someone (you didn’t mention this, but I’ll say it) like you would subsidize the higher priced wine, I’d be all over it every. single. year. Otherwise, I’ll take the wine I can afford to a “hypothetical” any day. 
I remember reading once that Les Forts was actually better than Latour in 1973. More recently, I found Moulin Riche 1999 to be as good as Léoville-Poyferré - understandably since most of the blend came from LP parcels and the cellar master at the time told me he thought they got the blend wrong. But otherwise, I’m with Neal on this - why choose second best? In comparative tastings against CBs, I’ve never seen second wines come out on top. But each to their own - it’s true that some second wines offer great drinking experiences.
2013 Montrose for $82 vs 2009 Dame de Montrose for $75 or 2010 Dame de Montrose for $70?
Apparently I have to be more specific so people don’t recommend village burg from a good vintage or something of the like. Also I wasn’t specifically talking about first growths if it wasn’t obvious.
delete
2013 Montrose. Easy decision. I’ve had and liked Dame in multiple vintages but it is a $30-40 wine in my view. Indeed, for $30-40 I think I could do much better buying the very best wine a producer could make from that vintage.
It’s a rare 2nd wine that lives up to the newly inflated pricing. Of course one could say the same thing about the Firsts, but I’ll go top wine, except in the case of truly train wreck vintages (e.g. 1991).
They were still experimenting then with how much they could and would F up Poyferre. By 2000 they had perfected it. The rest is history.
You can still find older, more mature vintages of Montrose for $80-100 if you look around. So I’d pass on it all.
Interesting. I would much rather have the 2nd wine from the better vintage.
This. I suspect that is our drinker’s mentality. We migrate to quality and value over label.
No, reg. Montrose the 2013 is not an outstanding and very interesting wine, easy pass for me, while Dame de M. 2010 IS outstanding indeed, and moreover cheaper.
However I agree that there are older (more mature) vintages available for less money …
In the past week I have opened the Cos d’Estournel and Montrose from vintage 2002. Both were drinking beautifully, and we did not ruin their experience by pouring comparatively better wines next to them. I do not own any Pagodes or Dame, from heralded or panned vintages, but based on many prior tastings of second wines I am confident they would not achieve the finesse or complexity we found in those first wines.
So for me, vintage characteristics notwithstanding, it should be first wines always. Never seconds. To back that position up, I bought heavily in seconds with the 2000 vintage. I sold them all years ago.