Earlier this week I passed the afternoon with a Cohiba Esplendido from 1999 accompanied with Van Winkle Family Reserve Rye (an "F" bottle).
What I found interesting about this combo is the VWFR displayed much more rye characteristics than I've previously experienced. The whiskey was more firery with a very pronounced mintiness. There were other herbal elements I don't recall detecting before as well. I also found the barrel to be more prominent during the initial intake. I figure to some, the experience described above might be a turn off as it might be quite a contrast to what one expects from this whiskey - a whiskey which to me could blindly pass for rye formula bourbon.
I'd add that the Esplendido also was altered during this session in my opinion. Typically stronger some of the flavors seemed to play background to the orchestra of the Van Winkle ensemble.
To me, this was a classic example of why you never know what to expect with cigar & whiskey pairings. I selected the Esplendido for strength with significant complexity thinking that the Van Winkle would play second fiddle with enough strength of it's own to match but not the kind of strength that would over power or conflict with the cigar at hand. Instead the whiskey took the lead and the cigar receeded somewhat into the shadows. Go figure.