There is one question that seems to be on the mind of Major League Baseball fans around the country, and maybe even in Chicago.
Was winning the 2016 World Series worth any potential future failures.
Most fans, and anyone who had wagered on the Cubbies to win its first title in over a century, would of course answer yes. The curse was broken, the North Siders got a title to celebrate, and in all honesty, it looked like the Cubs could contend for years with the roster intact.
But it did not work out that way, and Chicago’s momentum fell apart over the next couple seasons. Joe Maddon left as manager, and after the recent 2021 trade deadline was done, the whole team had been gutted and traded away to contenders.

This is where the question that was asked will come into play in earnest: the Cubs are now in rebuilding mode in the National League Central (and the National League), at a good time. The 2020 World Series champion Los Angeles Dodgers are set up to contend for the next half-decade (at least), the San Diego Padres look formidable, and so do the San Francisco Giants: and that is just the NL West.
So how can you make money betting on a team that looks to be in rebuilding mode? Pick your spots.
How can I make money betting on the Chicago Cubs?
For the rest of 2021, 2022, and maybe even into 2023, the Cubs might struggle. After they traded away Javier Baez, Kris Bryant, and Anthony Rizzo, all stalwarts on the title team, there will be a period of rebuilding through the newly replenished farm system.
But when you can back Kyle Hendricks on the mound, even if the odds are a little shorter, you might have to pull the trigger. Also, if the Cubs lose the first two games of a series at home, take them in the third game: even bad teams do not get swept at home very often.

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Which sports books can I use to bet on the Chicago Cubs?
- BetRivers
- DraftKings
- FanDuel
- William Hill
- PointsBet
- Barstool
Illinois betting sites and offers:
- BetRivers Sportsbook: get up to $250 matched with your first deposit
- DraftKings Sportsbook: welcome match up to $500 plus $500 risk-free first bet
- FanDuel Sportsbook: risk-free wager up to $1,000 on your first bet
- PointsBet: get up $250 matched with your first deposit
- William Hill: get up to $300 risk free wager
Where to watch/stream the Chicago Cubs
There are multiple ways to watch Chicago play every night on TV and/or your mobile device. The first way is on Marquee Sports Network, and also on multiple radio stations listed on the link. MLB Extra Innings and MLB.com also allow you to stream, as well as Fubo.TV.