Cy What: How Have the Cubs Fared Against The Best Pitchers in MLB?

Breaking: the Cubs haven’t exactly been the best team over the past few seasons. Big if true.

Still, they’re showing signs of life here and there, despite what will end up being a very pedestrian record. Consistency, however, remains an issue. In this month alone, they’ve managed to fit a 7-game losing streak between 3-game sweeps of division rivals Milwaukee and Cincinnati. Talk about a turd sandwich.

So what better way to top that tasty meal than a matchup with 2-time Cy Young winner (and likely on his way to a 3rd) Clayton Kershaw? Not to mention that opposing the imposing Dodgers ace is fresh-off-the-DL Edwin Jackson. Hooray. You know what they say: a sandwich just isn’t a sandwich without the tangy zip of an ass whipping. Or is it Miracle Whip? Either way.

But just the other day, the Cubs roughed up another Cy Young hopeful in Johnny Cueto, tagging him 6 earned runs over 5 2/3 innings. And that got me to thinking about how the Cubs have fared against other Cy Young-caliber pitchers.

Something seemed to tell me that they had really roughed up a couple of those guys over these past few lean years, like George McFly laying Biff out with a lucky punch. And while I’d prefer to simply make assumptions and let my beer-sodden memories stand as fact, I decided to plumb the depths of the interwebs to see if I was on point.

With that in mind, I looked at all the Cy Young winners from both leagues over the past seven years to see whether they had faced the Cubs in their given award-winning season. Oh, FanGraphs, you make things so easy. Since 2007, the Cubs have had eight matchups with pitchers who would go on to be named their league’s best pitcher that year.

Not surprisingly, seven of those games came against NL pitchers, with a 2010 game against the Mariners and Felix Hernandez representing their only tussle with an AL winner. R.A. Dickey is the only NL winner the Cubs did not face during that time, though they got Tim Lincecum three times.

All told, the Cubs have faced Jake Peavy (5/11/2007), Lincecum (7/3/2008, 7/13/2008, 9/25/2009), Roy Halladay (7/8/2010), King Felix (6/24/2010) and Kershaw (5/2/2011, 8/27/2013). In those 8 games, the Cubs have collected 50 hits, only 3 of which traveled over the fence, and have tallied 15 earned runs. They have walked only 10 times and have struck out 49. Sounds about right.

Things would look a lot worse for the Cubs were we to remove the Halladay game from the ranks though. Back in 2010, the Cubs worked Doc over but good, scoring 5 earned runs and striking out only thrice. Alfonso Soriano and Geovany Soto each homered in the game, which the good guys won 11-6. Maybe that’s what triggered my selective memory.

Despite being outscored 31-25 overall, the Cubs are 4-4 in their 8 games against that year’s Cy Young. They’ve split both games with Kershaw and the Dodgers as well, so the upcoming tilt serves as a rubber game of sorts. Can Edwin Jackson continue a run of three straight masterful pitching performances by the Cubs or will Clayton Kershaw maintain his dominant form?

I’m going to shift into “hope for the best and expect the worst” mode here. And who knows, maybe it’ll end up like the Bears game last Sunday, when I felt the same about their chances against the Niners. But what do you think? Can the Cubs pull it out?