What are the three ages at which to sample a wine to best understand its progression?

Yeah, you read me correctly.

Here’s what I would do with the bottom portion of your post, if opening this year:
Region Vintage Orientation for 2025

Region Varietal 1 2 3 4
Bordeaux (Left Bank) Red Bordeaux Blend 2014 or 2019 2000 or 2001 '89, '90, '95, or '96 1982
Germany Riesling (Kabinett) 2023 2019 2013 or 2015 2001 or 2010
Germany Riesling (Spatlese) 2019 2009 or 2010 2001 or 2002
Champagne NV 2023 2021 or 2022 2019 2012 or 2013 or 2014

I hand-picked particular vintages for tasting this year — tried to pick vintages that would both be showing well now and would provide meaningful contrast to the other three or two bottles. I didn’t do a 4th bottle for Spatlese not because there shouldn’t be a fourth bottle — there should (moreso than Kabinett and NV Champagne, imo) — but rather because my pre-2001 experience is so limited that I don’t feel comfortable making general vintage calls as I did elsewhere in this chart. But definitely find yourself an old Spatlese to try. Columns 3 and 4, in particular, kind of require a fairly high-quality wine; Columns 1 and 2 will see you have success with a wider range of selections.

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