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Best Classic Games to Watch With a Cigar

J. Bennett Alexander Alexander's picture

J. Bennett Alexander

Right now, we have the luxury of watching sports from the bubbles of the NBA and NHL playoffs. Major League Baseball struggles with playing a severely shortened season on their teams’ regular fields (with the exception of the Toronto Blue Jays), seemingly regularly interrupted by positive tests for the ongoing virus. As a backstop against these seasons ending soon and others possibly not beginning at all, we thought it would be wise to have a plan. So, we’re picking and recommending three classics. Three classic games to stream and three classic cigars to smoke while watching them. You’ll likely have your own ideas about the “best” games, and there are many more cigars to pair with those. Sorry, no golf matches this time around.

Baseball: Dave Roberts Steals Second Base

You want to argue for the Carlton Fisk home run in game six of the 1975 World Series? The Bobby Thompson “shot heard round the world?” Don Larsen’s perfect game in the World Series? A limping Dodgers’ Kirk Gibson homering against the A’s Dennis Eckersley in the 1988 World Series? Bucky Dent? Those are all fine, but did they help end an 86-year drought? What game and moment in a game match the emotion and magnitude of Red Sox pinch-runner Dave Roberts’ stealing second base on October 17, 2004? Do you remember?

The Yankees were up 3-0 in games in the American League Championship Series, one victory from another trip to the World Series. The Red Sox were down 4-3 in the 9th inning of game four. Mariano Rivera, the greatest closer of all time was on the mound for the Yankees. And he walked Kevin Millar. Boston manager Terry Francona sent in Roberts to run for Millar. Everyone knew why.

Rivera threw to first base three times in a row to hold Roberts close. Didn’t matter. Roberts stole second, sliding safely a split-second before Derek Jeter applied the tag. Roberts scored when Bill Mueller singled. Now the game was tied. Extra innings. You know what happened next. The Red Sox beat the Yankees four straight and did the same to the St. Louis Cardinals in the World Series.

Watch the whole game at

CIGAR PAIRING: This game took nearly four hours, so you’re gonna need a big cigar, maybe two. You could go with a 60 or even 70-ring gauge, but I think one or two Ashton VSG Sorcerers, 7 x 49, about $13, will really give you all the flavor and spice to match this great game. Ashton VSG (Virgin Sun Grown) is blended by Carlito Fuente and made at the Fuente factory in the Dominican Republic. The VSG carries a rare Ecuador Sumatra wrapper over a superb blend of full-bodied Dominican filler tobacco. This is a complex cigar with rich notes of earth, cedar, spice, and leather.

Basketball: Laettner Hits “The Shot”

I might have gone with Reggie Miller, of the Indiana Pacers, scoring eight points in nine seconds to beat the NY Knicks in game one of the first round of the 1995 Eastern Conference Semifinals. That was a great series of moments in action that lasted, actually, 8.9 seconds of playing time. But there is one that sticks out far more in my memory as a great basketball game, the whole game, that culminated in a spectacular moment on March 28, 1992. This was the Duke Blue Devils, the top seed, versus the Kentucky Wildcats, the number two, in the final of the NCAA Tournament’s East Region. The winner would go to the Final Four.

Kentucky had Jamal Mashburn as its biggest star. Duke, the defending champion, had Bobby Hurley, Grant Hill, and Christian Laettner. Laettner was often cited as the reason everyone outside of Durham, North Carolina, hated Duke.

This game was not just one final moment. It went back-and-forth throughout the regulation 40 minutes and went into a five-minute overtime. College basketball is exciting, but it’s often not the most well-played version of the sport. This game was all that. With 2.1 seconds left on the clock in overtime, Kentucky was ahead 103-102. Duke called time. Grant Hill would inbound the ball. No one guarded him. Hill threw a perfect pass to Laettner, standing on the foul line. Laettner dribbled once, turned and shot. Duke won 104-103 and went on to win the national championship for the second year in a row.

Watch at

CIGAR PAIRING: This game went about an hour and 40 minutes. I really like the idea of smoking a Padron 80 Years, 6.75 x 54 for this game. It’s an expensive cigar at about $32, but it’s a perfect Perfecto, beautifully constructed, tapered at both ends. It’s full-bodied and spicy and filled with Nicaraguan tobaccos. There’s a lot of nuts and coffee and cocoa on top of a foundation of earthiness and cedar. It’s available in a Natural and Maduro wrapper.

Football: Stealing Super Bowl XLIX

We’re talking the US kind of football. You could go with Super Bowl XLII in 2008, when the NY Giants defeated an up-to-then undefeated New England Patriots. It’s certainly a game worth looking at if only for what some call the “greatest play the Super Bowl has ever produced.” That was the catch made by the Giants’ wide receiver David Tyree, but only after NY quarterback Eli Manning somehow escaped being sacked. Anyway, Manning managed to throw the ball and somehow Tyree caught it, leaping, stretching himself as much as he could. You could go with that game. But I’m going with another Patriots’ Super Bowl, one many say they should have lost.

This was Super Bowl XLIX in 2015. The game was close and featured two great quarterbacks, Tom Brady of New England and Russell Wilson of Seattle. The game was tied at 14 at the half. The Pats rallied and took the lead 28-24 with 2:02 left in the game. Seattle drove to the Pats’ one-yard line. There were 26 seconds on the clock. Seattle called a pass play. The pass was intercepted. Pats win. Everyone still debates the call.

Watch the whole game here:

CIGAR PAIRING: This is a nearly two-and-a-half-hour commitment. I really like the A. Fuente Don Carlos Presidente, 6.5 x 50, at $11.90, for this game. This line is medium-bodied, but supremely complex. There’s a delicious Cameroon wrapper that encases vintage Dominican filler tobacco. Significant notes of earth and cedar, oak, espresso, and nuts characterize a classic profile. One of my favorite aspects of the Don Carlos line is the light sweetness of the finish. This is a very sophisticated cigar. And you might need two to get through the game! What a pity.

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