Ready for October? A weird season has produced an even weirder postseason, with 16 teams vying for the title, including two (!) clubs that finished with a losing record. The road to the fall classic begins this week with all eight wild-card series beginning on Tuesday (AL) or Wednesday (NL) and wrapping up by Friday. The postseason has never been more of a crapshoot, meaning World Series predictions have never been more difficult to pin down.

Will the best squads from July to September keep rolling? Will the wild-card round result in jarring upsets? SI's MLB experts predict the World Series matchup and winner, make a bold prediction and select a dark horse candidate to win it all. Here we go.

Tom Verducci

World Series Prediction: Dodgers over Rays (seven games)

Nothing happened this season to get me off my preseason World Series pick. The deepest pitching staffs in baseball proved their worth. No team has won more games using five or more pitchers than the Dodgers and Rays. The postseason format only enhances that strength; no off days in the first three rounds means depth of pitching is more important than in a typical postseason.

Dark Horse World Series Contender: Indians

Their pitching staff leads the majors in strikeout to walk ratio. They are an above-average defensive team. They are playing well down the stretch. (That’s a nice confidence boost, but history tells us there is no big advantage to being hot or not down the stretch, though it makes for a nice narrative.) They just don’t score a lot of runs, so their margin of error is small.

Bold Prediction

Like John Elway, Phil Mickelson, David Price and other athletes whose big game “legacies” were written prematurely, Clayton Kershaw, with his increased velocity and use of analytics (he throws the highest rate of breaking pitches in baseball, 59%), will have his signature postseason.