San Diego Padres v Seattle Mariners
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An MLB postseason like none other -- four rounds involving 16 teams determined by a 60-game regular season -- is in the immediate offing. To leaven something so roundly ahistorical, perhaps we need apply a light application of history. That's what we're here to do. We'll briefly run down the relevant postseason accomplishments for each of the 16 teams left standing and then put their 2020 postseason efforts to come in perspective. Best of all, we'll do so quite briefly in most instances. 

In our tabulations of playoff appearances and pennants, we're including anything as far as back as 1903, when the American League and National League first played the World Series and when we generally mark the onset of modern major league baseball. As well, we're also including each team's entire 1903-and-onward franchise history -- i.e., the Philadelphia and Kansas City A's are included with the Oakland iteration, the first Washington Senators are included with the Twins, and so on. 

Now let us meander. 

Atlanta Braves

  • Postseason appearances: 26
  • Pennants: 9
  • World Series titles: 3
  • Last World Series title: 1995

The Braves come in having not won a postseason series since 2001. That span includes eight NLDS losses and one loss in the NL Wild Card Game. Also, the Atlanta Braves once again have an opportunity to surpass the Milwaukee Braves and Boston Braves. Yes, the Braves' three titles have each come in a different city. The next Braves title means Atlanta takes the presumably permanent lead in this particular contest that's never been mentioned before now.

Chicago Cubs

  • Postseason appearances: 21
  • Pennants: 11
  • World Series titles: 3
  • Last World Series title: 2016

For the first time in franchise history, the Cubs have qualified for the postseason in five out of six years. And after going 108 years without winning a World Series, they have the opportunity to win their second title in just the last five years. Beyond all that, let's give a nod to civic supremacy. The Cubs have three World Series titles in total, which is precisely how many the crosstown White Sox have won. Should a Chicago team prevail in the 2020 postseason, then the tie will be broken. 

Chicago White Sox

  • Postseason appearances: 10
  • Pennants: 6
  • World Series titles: 3
  • Last World Series title: 2005

See just above for the Chicago municipal implications of the these playoffs. The White Sox are presently one of just 15 franchises to win three or more World Series. Get one this year, and they'll become one of just 12 franchises to win four or more. 

Cincinnati Reds

  • Postseason appearances: 16
  • Pennants: 9
  • World Series titles: 5
  • Last World Series title: 1990

The Reds are presently one of just seven franchises to have a winning record in postseason series while also winning at least 10 postseason series. Right now, they're 11-10 all-time in postseason series, so they'll need to prevail in the best-of-three wild card round to remain in such elite company. 

Cleveland

  • Postseason appearances: 15
  • Pennants: 6
  • World Series titles: 2
  • Last World Series title: 1948

As has been amply chronicled, Cleveland hasn't won a World Series since 1948, and at 71 years that's the longest current title drought in MLB. Overall, it's the fifth longest title-less stretch in MLB history. Here are the four ahead of them: 

  1. Cubs, 107 years (1908-2016)
  2. White Sox, 87 years (1917-2005)
  3. Red Sox, 85 years (1918-2004)
  4. Phillies, 77 years (1903-1980 -- Phillies' drought begins with the first AL-NL World Series in 1903)

Obviously, Cleveland wants to climb no higher on this list. 

Houston Astros

  • Postseason appearances: 14
  • Pennants: 3
  • World Series titles: 1
  • Last World Series title: 2017

For Houston, you've got a number of notable subplots. First, going all the way post-sign stealing scandal would provide a measure of validation and lay waste to the facile arguments that the Astros' recent triumphs were almost solely attributable to their rule-breaking. Second, an Astros World Series title in 2020 probably ensures that Dusty Baker will one day make the Hall of Fame for his managerial career. He's already the first skipper in big league history to lead five different teams to the postseason. As well, the Astros are vying to become just the fifth team to make four or more straight trips to the LCS. If they pull that off, they'd join the Braves (1995-99), A's (1971-75), Yankees (1998-2001), and Cardinals (2011-14). 

Los Angeles Dodgers

  • Postseason appearances: 34
  • Pennants: 22
  • World Series titles: 6
  • Last World Series title: 1988

The Dodgers not long ago secured their eighth straight NL West title, but as you see above they haven't won the World Series since '88. The "record" for most consecutive playoff appearances without a World Series title belongs to the Braves, who went to 10 straight playoffs (1996-2005) without winning it all. The Dodgers are obviously at risk of drawing closer that unfortunate mark. 

Miami Marlins

  • Postseason appearances: 3
  • Pennants: 2
  • World Series titles: 2
  • Last World Series title: 2003

While the Marlins have never won a division title, they do have two of something far more important -- World Series trophies. Indeed, the Marlins won both belt and title in 1997 and 2003 as a wild card team. In 2020, they'll once again be trying to win it all without a division title in tow. The Marlins enter the 2020 postseason with a 6-0 record in playoff series. They're the only current franchise to have never lost a postseason series, and that perfect record is hereby on the line. 

Milwaukee Brewers

  • Postseason appearances: 7
  • Pennants: 1
  • World Series titles: 0
  • Last World Series title: Never

Technically, MLB has had a losing team make the playoffs before. In 1981, when the season was shortened because of labor strife, playoff bids went to the winners of the first and second halves in each division. The Royals won the AL West in the second half with a record of 30-23. However, add their first half record of 20-30 into the mix and you get a final record of 50-53. This year, the Brewers and Astros have joined the club that is at once exclusive and quite the opposite of exclusive. 

For the Brewers, who have never won a World Series, this raises the question of whether they're the biggest underdog ever among MLB playoff teams. They finished the regular season 29-31, and across 60 games their opponents outscored them by 17 runs. That's despite the fact that the Brewers ranked near the bottom of the league in strength of schedule. Now take away their emergent ace Corbin Burnes, who's out with an oblique injury, and pit them against the Dodgers, who played at a 116-win pace this season. Now make the Brewers play those wild card round games on the road two time zones away. If they're lucky enough to escape against the heavily favored Dodgers, then the Brewers still must fight through three additional rounds to win the first World Series trophy in franchise history. Given the Brewers' dubious quality, the strength of their first-round opponent, and the breadth of the 2020 postseason, yes, Milwaukee may be the longest of playoff longshots. 

Minnesota Twins

  • Postseason appearances: 17
  • Pennants: 6
  • World Series titles: 3
  • Last World Series title: 1991

There's no denying the leading subplot for the Twins going into the playoffs: they've somehow managed to lose a record 16 straight playoff games. Need more? Thirteen of those losses have come against the Yankees, and the Yankees at this writing have won every playoff game in the history of Target Field. Lucky for Minnesota, they'll duck the Yankees in the wild card round, but regardless the pressure will be heavily on Minnesota to win a postseason game for the first time since 2004. 

New York Yankees

  • Postseason appearances: 56
  • Pennants: 40
  • World Series titles: 27
  • Last World Series title: 2009

Ah yes, the Yankees' embarrassment of baseball riches. What's further remarkable is that the Yankees didn't win their first pennant until 1921. That means the Yankees have won 40 of the last 99 American League pennants. Framing their dominance another way, just three teams -- the Dodgers, Cardinals, and Athletics -- have as many postseason appearances as the Yankees have World Series titles. Need more? Across their history, the Yankees have made the postseason 47.5 percent of time. In second place for this particular measure are the Diamondbacks, all the way back at 26.3 percent. 

Oakland Athletics

  • Postseason appearances: 29
  • Pennants: 15
  • World Series titles: 9
  • Last World Series title: 1989

The A's once again have an opportunity to join the Yankees and Cardinals as the lone teams to win 10 or more World Series. Oakland hasn't won it all since 1990. They haven't won a playoff game since 2013, and they haven't won a playoff series since 2006. 

San Diego Padres

  • Postseason appearances: 6
  • Pennants: 2
  • World Series titles: 0
  • Last World Series title: Never

The Padres are one of just six franchises to never win the World Series. The Rockies, Rays, Brewers, Rangers, and Mariners have also never hoisted the trophy. You can argue, though, that this is the best Padres team ever. The 2020 Padres put up the highest win percentage (.617) in franchise history, and if you look at their run differential their "deserved" win percentage (i.e., their Pythagorean record) was easily the highest in franchise history. To be sure, getting through four postseason series is a task not faced by prior squadrons, but this year's model is perhaps better equipped than any Padres team before it.

St. Louis Cardinals

  • Postseason appearances: 30
  • Pennants: 23
  • World Series titles: 11
  • Last World Series title: 2011

The Cardinals have won the most pennants of any National League franchise, but the mighty Dodgers are only one behind them. The Dodgers, by the way, are solid favorites to win their 23rd pennant in 2020. The Cardinals can obviously ensure they remain atop the historical heap in the senior circuit by winning the pennant themselves this season. 

Tampa Bay Rays

  • Postseason appearances: 6
  • Pennants: 1
  • World Series titles: 0
  • Last World Series title: Never

As noted above, the Rays are one of the six teams to never win a World Series, but since they've been around since just 1998 that's not exactly a grave indictment. The Rays this season are the No. 1 seed in the AL. Over in the NL bracket, two teams -- the Padres and Brewers -- have never won titles, as noted above. So if the Rays wind up paired with the Padres or Brewers in the World Series, then it'll be just the eighth time in MLB history that two teams to never before win it all have met in the World Series. Really, though, it's rarer than it sounds, as five of those World Series took place within the first six years of its existence. The last time was in 1980, when the Phillies prevailed over the Royals. 

Toronto Blue Jays

  • Postseason appearances: 8
  • Pennants: 2
  • World Series titles: 2
  • Last World Series title: 1993

The upstart Blue Jays had the youngest lineup in the majors this season with an average age of 26.0. The last team win a World Series with a lineup that young? That would be the upstart 1969 Mets with an average of 26.0.