With the wild-card games out of the way, the eight remaining postseason teams can produce 16 possible World Series matchups. Six feature pairs that have squared off before, producing memorable Fall Classic moments. Some of the other 10 matchups feature people who have seen life from both sides, while others require a deeper dive into the history books to find a common thread.
What follows here is an admittedly subjective ranking when considering those connections between pairs. This isn’t about which squads are the longest shots to come out of each league or whose weakness against lefthanded pitching would be exposed by their opponent, it’s about those historical hooks.
1. Red Sox vs. Dodgers: The Centennial
While these two teams paired up for a jaw-dropping 2012 blockbuster trade from which only Los Angeles first baseman Adrian Gonzalez remains in place, that’s hardly the primary hook. This year marks the 100th anniversary of these two teams squaring off in the Fall Classic, which would be the longest gap ever between World Series matchups. When Brooklyn got to the World Series in 1916 by winning its first pennant in franchise history, it was known not as the Dodgers but as the Robins, after popular manager Wilbert Robinson. Boston won in five, highlighted by a 14-inning, one-run complete game in Game 2 by a 21-year-old southpaw named Babe Ruth. A century later, Robin Span Jaffe—the daughter of Sports Illustrated senior baseball editor Emma Span and this scribe—was born in Brooklyn, her name inspired both by Jackie Robinson and by this anniversary.
2. Indians vs. Cubs: The Drought-Ender
This would pair the teams with the two longest championship droughts in baseball. Chicago's, of course, dates to 1908—as our most recent magazine cover reminds the world—and Cleveland hasn't won the World Series since 1948. These teams do have an important connection, however: A 1984 trade that sent struggling righthander Rick Sutcliffe from the Indians to the Cubs, where he turned his season around to the point of winning the NL Cy Young Award and helped Chicago return to the postseason for the first time since 1945. We can’t possibly jinx both teams at once, can we?
3. Red Sox vs. Cubs: The Theo Epstein (Double?) Cursebuster Special
This one is a marketing dream, likely to produce the highest TV ratings of any potential matchup. These two teams squared off in 1918, a date that should ring a bell: It was Boston’s last World Series win for 86 years and the third of Chicago's seven straight World Series losses. The star of the Series was Ruth, whose hitting and pitching exploits carried the Red Sox to a six-game win. Epstein, of course, was the Red Sox' general manager when the team ended the Curse of the Bambino in 2004—the first of two championships he won in Boston before jumping to the Cubs in late 2011 to become their president of baseball operations and lead their rebuilding effort.
4. Rangers vs. Dodgers: The Adrian Beltre Cooperstown Express
Closing in on 3,000 hits and 450 home runs (he has 2,942 and 445, respectively), Texas third baseman Adrian Beltre has become a lock for the Hall of Fame and belatedly emerged as one of the game’s most popular players. A matchup with Los Angeles would reunite him with the team that signed him out of the Dominican Republic as a 15-year-old (the Dodgers claimed he was 16) in 1994. Beltre was just 19 when he debuted in June 1998, and while he struggled that year, he developed into a standout defender with impressive power. He bashed 48 homers and racked up 9.5 Wins Above Replacement in 2004, his final season in Los Angeles, and after free agency carried him to Seattle and then Boston, he landed with the Rangers, whom he helped reach the 2011 World Series. He's flourished with Texas, as appreciation for his talents on both sides of the ball—not to mention his quirkier facets—has grown.
5. Blue Jays vs. Nationals: Oh, Canada
This one has an easy hook: Toronto—Canada's lone remaining major league team—against the team that descended from Montreal to move to Washington after the 2004 season. The Blue Jays put the "world" in World Series by winning back-to-back titles in 1992 and '93, but the Expos' bid to follow up a year later was cruelly cut short by the players’ strike. The game's changing economics eventually forced the team to become the wards of the other 29 major league clubs before being moved south.
6. Rangers vs. Nationals: A First Time For Everything
This is the only pairing guaranteed to produce a first-time champion. Such a matchup hasn't happened since 1980, when the Phillies beat the Royals, and prior to that it hadn't occurred since 1920 (see below). Texas lost its two previous Series appearances in 2010 and '11, and the Nationals have never made it that far, either in Washington or in their previous incarnation as the Montreal Expos. It's also the only matchup among these teams featuring an expansion team that has already changed cities. The Rangers began life as the Senators in 1961 and moved to Texas after the '71 season; the Nationals were originally the Expos, formed in '69 and transplanted to D.C. in 2005.
7. Indians vs. Nationals: Here's to You, Mr. Robinson
Frank Robinson was at the tail end of a Hall of Fame-bound career when the Indians traded for him on Sept. 12, 1974. A few weeks later, after the season ended, they named him player-manager, making him the game's first African-American skipper. He held that job for two-plus seasons, and later managed in San Francisco (where he became the NL's first black manager), Baltimore, Montreal and Washington, where he became the first manager of the Nationals. Despite the handicap of the team's uncertain business situation during its last days in Montreal, Robinson managed the Expos to 83 wins in both 2002 and ‘03, and led the Nationals to 81 in 2005, their first season after the franchise relocated.
Longest World Series Championship Droughts
8. Blue Jays vs. Cubs: Touch 'em All, Joe
One of the most dramatic endings to a World Series has its roots in this pairing. With the second pick of the 1981 draft, Chicago chose Wichita State outfielder Joe Carter, who would play just 23 games for the team in late '83 before being traded to the Indians in the aforementioned June '84 blockbuster that sent Sutcliffe to Chicago. Two trades later, Carter landed in Toronto in December 1990. He earned All-Star honors in each of his first four seasons there, not only helping the Blue Jays to back-to-back World Series titles but also becoming the second player to hit a championship-clinching–walk-off homer via his Game 6 shot off the Phillies' Mitch Williams in 1993.
9. Indians vs. Giants: Say Hey, Let’s Go Down That Dusty Rhodes Again
While this matchup could be a TV ratings nightmare given that it would feature the smallest markets in each league from among the remaining teams, there’s a cool history here. In 1954, a powerhouse Cleveland team won 111 games in the regular season with a pitching staff featuring a quartet of future Hall of Famers (Bob Feller, Bob Lemon, Hal Newhouser and Early Wynn), but the Indians were swept in four straight by a 97-win New York team. Game 1 featured Willie Mays's legendary over-the-shoulder catch of Vic Wertz's long fly ball—widely considered the greatest in baseball history—and was decided on a three-run walk-off homer by pinch-hitter Dusty Rhodes. Rhodes, who started just 32 games all year, came off the bench in Games 2 and 3 as well, going 3-for-5 in those games with another home run and four more RBIs. The World Series MVP award was first given out the next year, but had there been a winner in '54, it might well have gone to James Lamar Rhodes.
10. Red Sox vs. Giants: The Return of Snodgrass's Muff
These teams both reached their second World Series in 1912, and it was a classic, won in eight games (Game 2 ended in a 6–6 tie) by the Red Sox. Overshadowing the pitching heroics of Boston's Smokey Joe Wood and New York's Rube Marquard (a 0.50 ERA and two wins) and Christy Mathewson (a 0.94 ERA and three complete games, although he went 0–2) was an error by Giants centerfielder Fred Snodgrass in the 10th inning of Game 8. With New York ahead, 2–1, and three outs from the title, Snodgraff couldn't hold onto pinch-hitter Clyde Engle's routine fly ball, opening the door to the two-run rally that gave Boston the championship. In the annals of infamous plays that cost the early-20th-century Giants dearly, "Snodgrass's Muff" joined "Merkle's Boner" a base-running blunder by Fred Merkle that helped the Cubs win the NL pennant en route to their 1908 championship.
11. Rangers vs. Cubs: The Kyle Hendricks Experience
One of the first pieces in assembling this year's roster was a trade Epstein made four years ago. On July 31, 2012, the Rangers acquired Ryan Dempster from Chicago to bolster their rotation as they aimed for a third straight AL pennant. To get him, Texas gave up prospects Christian Villanueva, a third baseman ranked 100th on Baseball America's prospect list that spring, and Kyle Hendricks, a righty chosen in the eighth round in 2011 out of Dartmouth. Villanueva never panned out, but Hendricks cracked the Cubs' rotation in mid-2014, settled in as the team's fifth starter last year and broke out in a big way this year, leading the NL in ERA (2.13) and wedging his way into the Cy Young conversation. The Dempster-Hendricks trade was actually the first of two midseason deals between the two teams in as many years; in 2013, Chicago sent Matt Garza to the Rangers in a four-player swap that included current Cubs relievers Carl Edwards Jr. and Justin Grimm.
12. Blue Jays vs. Giants: Franchise Follies
Here’s a strange one: Had the Giants not been prevented from moving to Toronto in 1976, the Blue Jays wouldn’t exist! In January 1976, the Associated Press reported that the Giants had been bought by a group of investors that included Labatt’s Breweries, but the city of San Francisco went to court to prevent the franchise from breaking its lease on Candlestick Park. Bob Lurie stepped in to buy the Giants and keep then from moving, and Toronto was awarded an expansion franchise to pair with the one to which the AL had already committed in Seattle to begin play in 1977, with Labatt’s as owners.
13. Indians vs. Dodgers: The Ray Chapman Memorial
On Aug. 17, 1920, Cleveland's star shortstop Ray Chapman died of injuries sustained when he was hit in the head by a pitch from the Yankees' Carl Mays the day before. The stricken Indians, with 21-year-old callup Joe Sewell at shortstop, nonetheless held on to win their first pennant and faced the Dodgers (again, actually the Robins at the time). Though Sewell made six errors in the Series, Cleveland's stingy staff held Brooklyn to just eight runs (six earned), winning the best-of-nine in seven games.
14. Blue Jays and Dodgers: Anthopoulos and Them
Toronto's current roster was built in large measure by Alex Anthopoulos, who spent seven seasons (2009–15) as the club's general manager. The Blue Jays finished higher than fourth in the AL East just once in his first six years, but in 2015, they won 93 games and reached the postseason for the first time since 1993. Anthopoulos's bold July blockbusters to acquire shortstop Troy Tulowitzki from Colorado and lefthanded starter David Price from Detroit helped Toronto pull away from the pack and win the division title. The Jays reached the ALCS, but Anthopoulos, who was in the final year of his contract, rejected an extension after the team brought in Mark Shapiro as president and CEO. In January, he became the Dodgers' vice president of baseball operations, making him one of four former GMs (along with Josh Byrnes, Ned Colletti and Gerry Hunsicker) working under president of baseball operations Andrew Friedman.
15. Red Sox vs. Nationals: The Sandy Leon Invitational
He has been overshadowed by the performances of many of his teammates this year, but 27-year-old catcher Sandy Leon has been a big part of Boston's success. He began his career with the Nationals, for whom he played 34 games over three seasons from 2012 to '14 and hit an anemic .187/.258/.225 with one home run in 235 plate appearances. Despite that showing, Boston acquired him in March of 2015, and when he came up from Triple A Pawtucket this June, he quickly seized the starting catching job that had been made available by Christian Vazquez's struggles and Ryan Hanigan's injuries. Even with a season-ending 4-for-44 slump, Leon finished the year at .310/.369/.476 with seven homers in 283 PA.
16. Rangers vs. Giants: Didn't We Do This Already?
Of all the World Series pairings that have previously occurred, this isn't just the only one that's already happened in this millennium; it's also the only one that's happened in the past 60 years. These two teams squared off in 2010, and if you can't remember it, you're forgiven. San Francisco's five-game triumph kicked off their run of even-year voodoo and included gems by Madison Bumgarner and Tim Lincecum, but Game 1 was the only contest in which the lead changed hands. As many as nine players who appeared in that series could be part of the rematch.