The Boston Red Sox bookended last season with two of the worst losing streaks in recent memory, starting the year 2-10 and then finishing it 7-20 in September. Their miserable stretch only ended because there were no more games to lose. It was the game’s worst collapse in history, coughing up a 9 1/2 game Wild Card lead to miss the playoffs. That paved the way for the entire locker room to be ravaged, gutting many of the team’s personnel, including manager Terry Francona.

And still, they avoided losing 20 games in a row. That kind of a feat takes determination, and ineptitude. Although a longshot, Bovada is offering a juicy +900 payout in MLB Prop Betting Odds if a team loses 20-straight.

You’d have to go all the way back to 1988 to find the most recent 20-game loser when the Baltimore Orioles dropped each of their first 21 games – taking bettors only one game over the minimum to reap their winnings. The Orioles fired their manager before they actually one a game and finished the year with only 54 victories.

The longest losing streak in baseball’s modern era came in 1961 when the Philadelphia Phillies, the game’s losingest team in history, dropped 23 in a row on their way to a 47-107 season.

The only other time a team lost that many games was in the Montreal Expos’ inaugural year. Their historically bad year began early when they started 11-17 before losing exactly 20 games in a row, and losing 110 overall.

The MLB is getting top-heavy lately with a lot of stardom moving to the American League. The Houston Astros have some real potential to be terrible, people. Losing 20 in a row isn’t out of their price range. Seattle lost 14 in a row last year, and have essentially the same team again, so don’t count them out either.