1969 New York Yankees (80 wins) vs. the 2009 New York Yankees (103).
There are many worse teams in this tournament than the '69 Yankees, but they will be decided underdogs in the first round. The '09 team won the World Series and has the second-highest regular season win total in this tournament. The 2009 Yankees, as the top seed with the most single-season wins, will have home field advantage in any series they play.
1969 Cleveland Indians (62 wins) vs. the 2009 Cleveland Indians (65 wins).
Two bad seasons, which is how you wind up with an eighth seed. The '69 squad does have Sudden Sam McDowell and Luis Tiant. The '09 team doesn't even have Victor Martinez; he was traded in midseason and is on the Red Sox roster.
1969 Cincinnati Reds (89 wins) vs. the 2009 Cincinnati Reds (78)
The '69 Reds outfield is pretty imposing. Pete Rose, Bobby Tolan and Alex Johnson each hit well over .300. Add in the power of Johnny Bench, Tony Perez and Lee May, it's an imposing lineup (until you see the middle infielders). The '09 Reds have Joey Votto and little else. Both teams were a year or two away from emerging.
1969 Washington Senators (86 wins) vs. the 2009 Texas Rangers (87)
The only winning record in Washington Senators history, right here. Frank Howard hit 48 homers. Dick Bosman led the American League in ERA. This is the closest of any first round pairing in terms of wins.
1969 Detroit Tigers (90 wins) vs. the 2009 Detroit Tigers (86)
The '69 Tigers were a distant second in the AL East to the juggernaut Orioles, but Denny McLain did cop a share of the Cy Young Award. The '09 team will be remembered for its late fade -- the Twins beat them in a Game 163 for the AL Central title -- and for Miguel Cabrera's drunken spree in the final weekend that landed him in jail. Somehow Miggy's reputation has survived that.
1969 Houston Astros (81 wins) vs. the 2009 Houston Astros (74)
The '69 Astros are part of the backdrop for Ball Four, which, as I said in introducing this tournament, is part of my interest in the 1969 season. The '09 Astros don't do much for me, and I can see, looking back, why the new management decided to do a complete teardown.
1969 Seattle Pilots (64 wins) vs. the 2009 Milwaukee Brewers (80)
And the Pilots were the other part of the backdrop for Ball Four. Theoretically, Jim Bouton could start against Jim Bouton if the '69 Pilots and the '69 Astros should both advance to the third round. Not real likely, but if they do play each other, Bouton will face Bouton.
1969 Atlanta Braves (93 wins) vs. the 2009 Atlanta Braves (86)
Henry Aaron, Phil Niekro and Orlando Cepeda from the '69 Braves are all in the Hall of Fame. Chipper Jones from the '09 version will be, but it's a low-grade, near-the-end-of-the-line version of Chipper.