1969 Boston Red Sox (87 wins) vs. the 2009 Boston Red Sox (95)
I was a bit surprised the Red Sox snuck onto a top line, but here they are. The '69 Sox had an imposing outfield: Carl Yastrzemski hit 40 homers, Reggie Smith hit .309 with 25 homers and Tony Conigliaro returned from a devasting eye injury to hit 20. (But Yaz, who had won batting titles in both 1967 and 68, hit just .255, and Tony C.'s percentage lines are not impressive.) Rico Petrocelli hit 40 dingers, impressive for a shortstop outside the steroid era. The '09 Sawx won more games; I'm not sure they were a better team.
1969 San Diego Padres (52 wins) vs. the 2009 San Diego Padres (75)
A first year expansion club on one hand, and just a subpar team 40 years later. Both teams got almost all their offense from their first baseman: Nate Colbert in 1969, Adrian Gonzalez in 2009.
1969 Oakland Athletics (88 wins) vs. the 2009 Oakland Athletics (75)
The '69 A's were showing signs of their early 70s dynasty in 1969. Reggie Jackson hit 47 dingers, Sal Bando hit 31, and Rollie Fingers started making a home for himself in the bullpen. The talent was still settling in, The 2009 A's bore no resemblance to the team that reached the playoffs in 2012-14.
1969 Baltimore Orioles (109 wins) vs. the 2009 Baltimore Orioles (64)
There is no wider gap in first round pairings than this: 45 games. The '69 Orioles are a scary good team. The 2009 Orioles are bird food.
1969 Chicago Cubs (92 wins) vs. the 2009 Chicago Cubs (83 wins)
The '69 Cubs are the fall guys to the '69 Mets legend. (So are the Orioles, but the World Series can be seen as a fluke.) Ron Santo, Fergie Jenkins, Ernie Banks, Billy Williams -- four Hall of Famers without a division title, much less a pennant or World Series to their credit together. The '09 Cubs had a winning record, but not that kind of talent.
1969 Philadelphia Phillies (63 wins) vs. the 2009 Philadelphia Phillies (93 wins)
Not as large a mismatch as the Orioles series, but a pretty serious one. I had forgotten until I was going through the '09 cards that Pedro Martinez finished his career with the Phils. It's also difficult to see how I'm going to get him into the rotation. The '09 Phillies lost the World Series to the Yankees; they're a serious threat to win this tournament.
1969 Kansas City Royals (69 wins) vs. the 2009 Kansas City Royals (65)
How bad were the '09 Royals? Zach Greinke won the AL Cy Young for them, and they still won four fewer games than their first-year expansion team counterpart.
1969 Los Angeles Dodgers (85 wins) vs. the 2009 Los Angeles Dodgers (95 wins)
The 1969 Dodgers are the one team I'm tempted to let go with just three starters. Claude Osteen, Bill Singer and Don Sutton averaged more than 300 innings apiece. Nobody else has three workhorses like that. The '09 Dodgers have a really deep outfield: Manny Ramirez, Matt Kemp, Andre Ethier and Juan Pierre,who merely hit .308.