The wild-card game is the first (and sometimes only) "go big, or go home" spot for a team looking to win the World Series. It's a one-game play-in to the division series with the loser headed home for the winter. As such, it should come as no surprise that teams are known for rolling out their absolute best starter in order to try and get the job done. They're also not likely to be afraid to ride their best bullpen arms -- or even other starters if need be.
This year is a bit different, however, as both teams also tied for the in-season divisional crown and, as such, had to play their rivals in a one-game tiebreaker on Monday. So theoretically, what we should actually see is both teams' second-best starter. That is certainly the case for the Rockies and Kyle Freeland.
Strangely, though, it's not even remotely true for Chicago. Joe Maddon has a reputation as being a "mad scientist, genius-type manager" who is always thinking one step ahead and making outside-the-box moves that other managers don't even consider. However, this reputation could not be more unwarranted. The number of clear and obvious errors (to any sabermetrician, at least) that Maddon made in the Cubs' 2016 World Series run was astounding. The Cubs actually won in spite of Maddon, not because of him.
If Chicago is to make it to the NLDS this year, it will once again have to do it in spite of him. That's because the choice of Jon Lester robs the Cubs of roughly 7 percent of their chance of winning this game.
Here are some more thoughts on Tuesday night's game:


Colorado Rockies (Freeland) +125 at Chicago Cubs (Lester) -135
Lester is a bad choice for two primary reasons. The biggest is that not only is he not the Cubs' second-best pitcher; he's actually their second-worst stating option, ahead of only Mike Montgomery. There's a pretty significant drop-off between the team's top three starters and Lester.
Despite competing for a Cy Young just two seasons ago, Lester has rapidly fallen off over the past couple of seasons, becoming no more than an above-average pitcher at best. His 3.32 ERA may still appear to be great, but he was helped out significantly by a very lucky 80 percent LOB rate. When you look under the hood, you see that he's coming off his second consecutive season with a FIP and SIERA over 4.00. THE BAT projects him as a true 4.14-ERA pitcher in a neutral context, which is considerably worse than Jose Quintana, Kyle Hendricks, and Cole Hamels -- all of whom project out in the 3.50-3.75 range -- and barely better than the 4.20 league-average ERA this season for starting pitchers.
The second reason Lester is a bad choice is because he's left-handed. He projects for a smaller platoon split than your typical left-handed pitcher, yes, but he's left-handed nonetheless. Four of Colorado's five best hitters (Nolan Arenado, Trevor Story, Matt Holliday, and DJ LeMahieu) are right-handed and will hold the platoon advantage. Charlie Blackmon is the lone LHB in this group, while David Dahl ranks sixth. Leveraging platoon advantages is one of the best ways for a manager to have an impact on a game, and Maddon's choice of Lester completely fails in this effort.
If the Cubs lose this game, you can place no less than 7 percent of the blame on Maddon's shoulders -- which is far more impact than any manager ought to have on an outcome before a game even starts. Using Hendricks instead, both a better pitcher and a right-hander, would give the Cubs back that extra 7 percent chance of winning. It would also put my projection for this game much more in line with Vegas' assumption that the Cubs are a solid favorite at -135. As it stands, though, I have this game projected much closer to a pick' em.
This Vegas line actually looks very out of whack to me. I have to think a big part of it is just the perception that Lester is a good pitcher (which he simply is not anymore) and that Freeland is a generic one (which is also not true). Freeland is a significantly better pitcher than Lester and a legitimately good one overall. He posted better peripherals across the board this year, despite playing half of his games in Coors Field, baseball's top hitters' park.
Like Lester, he's a left-hander, and he'll face a potentially righty-heavy Cubs lineup, but he sets up way better than Lester does. Three of Chicago's four best hitters are left-handed (Anthony Rizzo, Daniel Murphy, and Kyle Schwarber), which will force Maddon to either deal with not having the platoon advantage or to start lesser hitters like Albert Almora Jr. and David Bote. For those wondering, starting the lesser hitters is the correct mathematical choice, given that Freeland's projected split is pretty extreme, but the quality of the lineup diminishes either way.
This is, of course, the exact opposite of the situation Lester faces and it gives the Rockies a true fighting chance here, despite having both a weaker offense and a weaker bullpen than Chicago does overall. The Vegas line projecting the Cubs as a clear favorite looks far too aggressive, hence the following pick.