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The 12 Days of Cubsmas, Day 4: Four postseason appearances in a row

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This is the longest postseason streak in the history of the team

The Cubs celebrate after winning the 2016 World Series
Photo by Ezra Shaw/Getty Images

In 2018 the Cubs made their fourth postseason appearance in a row. What may have been lost in the disappointment of a 13 inning loss to the Rockies was that this was the first time in the history of the franchise that the Cubs have played postseason baseball four seasons in row.

I really can’t overstate how many years this is. How many Cubs fans never saw a team play at this level for this length of time. It really requires some visuals, so please indulge me for a bit with a series of screenshots. First, up the last 22 years of Cubs history:

Recent postseason Cubs history
Champs or Chumps

While Cubs fans have had a lot of postseason appearances in the last 22 years, most of them have been quick exits. The last four years stand out as distinct in this category, even before you take a trip down memory lane and realize it contained the greatest moment for the Cubs in over 100 years:

Anthony Rizzo presents the World Series Trophy at the 2017 home opener
Photo by Jonathan Daniel/Getty Images

For years, it wasn’t even just that there weren’t World Series trophies, or that there weren’t playoff victories. From 1926 to 1995 the Cubs were only in the postseason seven times. There just weren’t really playoff games at all, let alone successful ones:

Less recent history of Cubs postseason appearances
Champs and Chumps
Less recent history of Cubs postseason appearances part 2
Champs and chumps
Less recent history of Cubs postseason appearances part 3
Champs and Chumps

I mean, beyond that, there was a stretch from 1946 to 1983 where there were zero postseason appearances for the Cubs. A Cubs fan born in 1946 would have been 38 years old before they saw their team in the postseason. That same person would have been 57 years old before they saw the Cubs win a postseason series.

You need to go back to 1945 and earlier to find an era when the Cubs made frequent appearances in the postseason. I love historical sleuthing as much as anyone on BCB, but it’s worth remembering that the last time Cubs fans saw a World Series on the North Side of Chicago Wrigley Field looked very different:

1945 Wrigley Field
Getty Images

To find the last time the Cubs were in the playoffs three times in a row, you have to go back to the West Side Grounds:

It was over 100 years ago the last time the Cubs went on a postseason run like this
Champs and Chumps
west side grounds
West Side Grounds saw the last golden age of Cubs baseball
Chicago History Museum

So on the fourth day of Cubsmas, let’s take a moment to celebrate some of the incredible moments from the last four years of Cubs playoff baseball. Here are my favorite moments from each year:

2015: A Schwarbomb

There were a few possible Kyle Schwarber shots that I could have used for 2015, but this moonshot that still lives on the video board in right field (or as I like to call it, the Schwarboard) was not only a towering home run. It was a dagger in the hearts of Cardinals fans and in retrospect signaled a sea change in the NL Central [VIDEO].

2016: The drought is over

There are so many brilliant moments from the 2016 postseason, but in the end it’s all summed up by this one [VIDEO].

2017: Jake wins his last start as a Cub

There were a few contenders for me for this moment, including some wild moments from the Cubs and Nationals NLDS, but ultimately my favorite memory from 2017 is that Jake Arrieta came through in the postseason again. In his final start as a Cub, without his best stuff, with a little help from two monster HRs from Javier Baez and a solo shot from Willson Contreras, he kept the Cubs in the postseason [VIDEO].

2018: Pedro Strop pitches through pain

The Wild Card Game had a lot of moments we would have looked back on as incredible if the game had gone the Cubs’ way. But it didn’t, and so rather than celebrating Terrance Gore’s incredible baserunning, or Javy hugging Nolan Arenado at third, I wanted to turn #HatsLeft for a moment and celebrate the one and only Pedro Strop, who managed an incredible performance through pain keeping the Cubs in the game in the ninth. The 2019 Cubs will start the season without Brandon Morrow and I have a hunch we’ll be seeing a lot more of ninth inning Strop [VIDEO].

And so, on the fourth day of Cubsmas let’s celebrate four postseason appearances in a row.

On the fourth day of Cubsmas my true love gave to me, four postseason appearances in a row, three epic relief performances, two walkoff grand slams, and a Javy MVP candidate.