I know what you’re thinking. The World Series literally ended last week, Garion. Why should I be placing bets on an event that’s a full year away? Why should I be placing bets on an event that might not even 100% happen due to the upcoming labor dispute?
All great questions. However, you have to remember that uncertainty begets value in betting. There are teams who will see a massive odds shift between now and April. Heck, with a truncated and expedited free agency expected to take place across November, there are teams whose odds will shift massively in the next couple of weeks. Let’s get ahead of it.
Here are three entirely too early World Series best bets to consider, as we all hunker down for the winter.
2027 World Series Odds on DraftKings Sportsbook
Boston Red Sox (+1100)
For the second year in a row, the Red Sox flamed out in the Wild Card round against the rival New York Yankees. However, there were a lot of positives to take from the season, especially when you consider that Boston only got 242 plate appearances from Roman Anthony and six starts from Garrett Crochet.
If those two key pieces can bounce back and stay healthy in 2027, there’s already a lot of room for internal improvement with the Red Sox. That’s not to mention full seasons from deadline additions in Adley Rutschman, Curtis Mead and Erik Miller; and the eventual promotion of Franklin Arias, who is currently listed as the No. 2 prospect in all of baseball after tearing up Double-A and Triple-A as a 20-year-old in 2026.
What will really be interesting is how active Boston and CBO Craig Breslow are in free agency. Tom Werner’s infamous “full throttle” comment from a few years back still rings hallow among most Red Sox fans, even after the organization spent $130 million on Ranger Suarez last winter. Boston had the 10th-highest payroll in MLB this past season, so this isn’t a franchise that’s bereft of financial might. That said, the Red Sox of a decade ago consistently spent like a top five team. Could we see a shift back to that level of frivolousness? If so, this roster could be loaded come Opening Day.
Atlanta Braves (+2500)
After winning 94 games and making the NLDS, I’m a little surprised to see the Braves’ odds sit this low. It’s not like Atlanta is losing a ton of big-name assets in free agency, either. The two players to note would be Raisel Iglesias and Tyler Mahle, yet it wouldn’t exactly be a shock if Alex Anthopoulos brought both of those men back. I also don’t think those would be the Braves’ only significant moves.
Atlanta was unusually quiet during the last free agency period, only bringing in Robert Suarez on a three-year deal. The club was then notably stagnant at the trade deadline, though there were reports that the Braves tried desperately to loosen Jacob deGrom from the Rangers to no avail. This run of apathy can’t continue. In reality, 2027 and 2028 feel like the end of this group’s window to contend. Ozzie Albies’ contract is up after next season. Ronald Acuna Jr. and Chris Sale each have two years left on their agreements, and the latter will be 38-years-old by the end of March. Matt Olson and Sean Murphy aren’t quite as old, but both are reaching the end of their primes, too. Now is the time to push the chips into the middle of the table.
Pitching is the big question mark with this roster. Spencer Schwellenbach and Spencer Strider should be back in 2027, though I don’t know how much I can expect from Strider at this point, nearly three years removed from his peak. On a more upbeat note, flamethrower Didier Fuentes could be ready to make the jump to the rotation, after posting a 2.45 ERA and a 2.60 FIP out of the bullpen in ’26. Still, the Braves bringing in a Sonny Gray or a Michael King would be a massive lift to the floor of this somewhat worrisome unit.
Toronto Blue Jays (+4000)
I’m just having a bit of a hard time wrapping my head around how the market views Toronto.
Coming off a World Series appearance in 2025, the Blue Jays were one of 2026’s most disappointing teams. Toronto ranked dead-last in ISO (.134) and expected wOBA (.298), and there’s now a huge question mark moving forward about the ability of Vladimir Guerrero Jr. after his horrendous campaign. I’m not going to sit here and suggest there are no red flags with this club, or that they don’t play in MLB’s most competitive division. However, these odds seem far too high for an organization that has consistently shown a willingness to spend in recent years.
To that point, is there really that big a difference between the Jays and the Mets (+2200)? Other than the fact Toronto has won more games than New York each of the past two seasons and that it inhabits the league without the Dodgers (+310) and the Brewers (+500)?
Again, I’m not even necessarily suggesting that the Jays are a good pick to win the World Series, just that their odds are off, and now is the time to take advantage of that mistake. With George Springer, Kevin Gausman, Shane Bieber, Yimi Garcia and Myles Straw now off the books, Toronto has a lot of money to spend, and I’d shocked if it didn’t address its floundering offense with multiple additions, headlined by the likes of Seiya Suzuki, Teruaki Sato or Brandon Lowe. The Jays could also be in on the pitching market. Remember, they’ve been a main character of the offseason each of the past two years.
At the end of the day, this is an organization in a massive market that picked up the tab on a top five payroll in both 2025 and 2026. Once it flexes a little financial muscle in free agency, these odds are going to fall. Might as well get in now.
