Cover Challenge: Churchill Vs. JFK

Cover Challenge: Churchill Vs. JFK
Cigar Aficionado’s Cover Challenge has come down to Sir Winston Churchill, left, versus John F. Kennedy.

We have our finalists in Cigar Aficionado’s 25th Anniversary Cover Challenge, and oh what finalists they are.

Two legendary statesmen are squaring off in the final round of this challenge: Sir Winston Churchill, the former Prime Minister of the United Kingdom, is taking on John F. Kennedy, the 35th President of the United States.

Churchill made his way to the final round by getting more votes than the Fuente family. Before that, Churchill eliminated Michael Strahan in the opening round, then outdid actor Matthew McConaughey before facing down cigar smoking icon George Burns in the Sweet 16. He then took on The Sopranos before his showdown last week with the Fuentes in the Final Four.

JFK took down R&B star Usher in the opening round of voting, then supermodel Claudia Schiffer. He faced down Jeff “The Dude” Bridges in the Sweet 16, took on Tom Selleck the week after that and last week outgunned legendary actor Jack Nicholson in our Final Four.

Voting has already begun for this final round, which ends on Sunday. Cast your votes now for your favorite cover. Every time you vote, you are entered into a  sweepstakes where you can win a box of specially aged cigars from the humidor of Marvin R. Shanken that are nearly as old as Cigar Aficionado magazine itself.

The winner of the sweepstakes and the winning cover will be announced here at

Vote Now!