The Cubs Enter Spring Training As Defending World Series Champs … And It Still Seems Weird

The Chicago Cubs won the World Series in 2016.

After a lifetime of being reminded about 1908, that lead sentence is worth repeating again. Yet, it still seems surreal – three months later – that the World Series champion Cubs is still a thing.

My mother recently asked me if at any point I thought the Cubs would never win the World Series in my lifetime. And my answer surprised her.

“Yep.”

Allow me to explain.

In 2008, I had a come to Jesus meeting with baseball as I watched a Cubs team that ran through the rest of the National League get swept in convincing fashion by the Los Angeles Dodgers, while surrounded by Cardinals fans. It was only then – between swigs (chugs?) from the Jack Daniels bottle purchased earlier that evening – when I realized how difficult it was to actually win the World Series … especially when compared to other sports.

For example, FiveThirtyEight gave the Cubs a 77% chance of making the playoffs before the 2016 season started, but only an 11% chance of winning the World Series. That’s quite a disparity. Compare that to the NBA, where the Warriors currently have a 99% chance of making the playoffs, but a 54% chance to win the NBA title. Minimal disparity, comparatively speaking.

Maybe you’re a Yankees or Cardinals fan reading this and laughing with your 38 combined World Series titles. But if you’re laughing, it probably means you haven’t had that moment. And when you do, it’s not going to be pretty.

Because here’s the thing about winning a World Series, as I explained to my mother. From 1909-1968, winning the World Series was relatively easy. It involved the simplest of plans: Win the most games in your league (thus, capturing the pennant) and win a best-of-seven series and take home the World Series title.

Simple enough. Be the best team in your league, beat the best team in the other league. The Yankees won 20 of their 27 World Series titles under that format, the Cardinals won eight. Be the best. Beat the best. It’s a formula as old as sport itself.

What made the Cubs drought so frustrating was that in those simplest of times, they only made seven World Series appearances in those 59 years, with the last being in 1945.

Things became a little more difficult in 1969 with the addition of divisions and the League Championship Series. Even still, we’re talking about a relatively simple formula. Be the best team in your division, win the pennant by beating the other division winner in a series, and win the World Series.

This was your format from 1969 until 1993 – a 24-year stretch in which the Cubs made the playoffs just twice.

The Cubs wasted 84 years of the the most straight forward path to a World Series, while their longest-standing rival thrived.

Can you see how a long championship drought manifested itself?

The Wild Card era added a new wrinkle and another team to the mix and the Cubs found their way into the playoffs four times from 1994 to 2011, but managed one playoff series win.

So there I am on a couch in Carbondale in 2008, drinking and thinking about how the best teams don’t always win the World Series.

The 1984 Cubs had the best shot of them all, but had to play three road games in San Diego despite having the NL’s best record. Nice league set up, gents.

The 90s had the dynasty Yankees, but also the Braves who won a bajillion division titles with three Hall of Fame pitchers in their prime – but only one World Series win and an Indians team that probably should have won a title or two, as well.

So, leave it to the Cubs to figure it all out when the odds are the longest. Check out this road map to a World Series:

• Win your division with the best record in the league as to avoid playing in a one-game playoff and start your postseason on the road against the best team in baseball in a short series.
• Win your LDS series, which is a tough enough challenge on the surface, made more difficult in that if you’re a Wild Card team, your best pitcher throws only once in a five-game set, twice if you’re lucky. But if you’re truly lucky, you win in four to leave your best starter to start LCS Game 1.
• Win the LCS. Simple enough. But if you’re a Wild Card winner that happens to have more wins than a division winner, you get to start on the road again. Fun times.
• Win the World Series, where prior to 2017, home-field advantage was decided by whichever team won the All-Star exhibition game.

I don’t have to squint to see a Cubs dynasty in the making. Two MVP candidates at the corner infield spots, a steady defensive shortstop with 20-homer pop, an All-Star caliber utility player, and a World Series/postseason legend with fewer than 300 plate appearances at the big league level — all under team control for at least the next five years.  Defenders who can back-up hurlers who pitch to contact and a catcher who can shut down the running game. And a front office with money to spend and intelligence to find and exploit the next trend and/or loophole before anyone else.

The Cubs should be among favorites to win the World Series for the next few years, but it’ll never be easy — statistically speaking.