Best World Series Sleepers Entering the 2021 Stretch Run

By Dan Vasta in MLB
| August 14, 2021 5:52 am PDT

The MLB playoffs make the month of October jam-packed with excitement.

The lead up to the World Series brings new moments in baseball we have never witnessed before. The dreams and aspirations of so many teams become a reality, and upsets turn into disappointments and sometimes losses.

Which teams should you put your money on in October? You can certainly target the top 2021 World Series contenders following the MLB trade deadline, but there could be more money to be made.

With an eye on some better prices, here are your best World Series sleepers entering the 2021 MLB stretch run.

San Diego Padres (+1100)

This team is safe to make the postseason over the Reds for the final wild-card berth. The Reds bullpen has been less than stellar for most of the season (bottom five, ERA north of 5), and their offense single-handedly cannot carry them to a spot.

The Padres have a better bullpen and are too potent to take a pass on.

The ability they have shown throughout the season is worth an attempt to roll in the dough. The value was much shorter a month-plus ago, so this is a good time to pounce. We could see the odds get even longer once Labor Day weekend arrives.

Fernando Tatis Jr. is a player that is capable of going bonkers in a series. He’s also finally nearing a healthy return.

With their best player in tow, the Padres are good enough to get past the Brewers or the Phillies in the NLCS.

Getting past the Dodgers and or the Giants along the way will be the challenge. Both teams have proven to have better situational pitching, but the home-run ball has been a true equalizer in October.

Tatis, Manny Machado, and Eric Hosmer have had postseason success over the years.

Machado went all the way to the ALCS in 2014 before getting swept by the Royals. Hosmer was on the Royals squad that was simply flawless with their clutch hitting and lights-out bullpen.

Mark Melancon brings plenty of experience, but other arms in the pen can help bolster any end of game situations. Drew Pomeranz, Tim Hill, and Emilio Pagan are all capable pitchers that can produce.

Yu Darvish and Joe Musgrove are both All-Star caliber pitchers. The ballpark will benefit both as we approach October. Musgrove and Darvish have not gone more than seven innings in many games, but the franchise will have a lead when the tandem takes the mound.

The lineup is capable of exposing top aces on opposing teams. That is why there is value here.

Jake Cronenworth has some Chase Utley in his game from an offensive standpoint. The infielder can play everywhere on the field but has solid pop for the Padres. He can bat anywhere in the lineup and has a knack for driving in runs while the pressure is on.

Throw in the addition of Adam Frazier, and this team has plenty of pieces. Knocking off the Giants and Dodgers in back-to-back matchups will be challenging. Still, they have the goods to do so and are a sleeper to take.

Boston Red Sox (+1500)

The Red Sox are not a mortal lock to reach the postseason, but their lineup can take them to the promised land. Boston has three MVP-like boppers in the lineup; J.D. Martinez, Rafael Devers, and Xander Bogaerts can mash with the best of them.

The trio is up there with anybody in the league.

The ability to hit the long ball will allow them to win the whole ball of wax. Fenway Park is the perfect place to rake in October, and the right-handed hitters have taken advantage of the green monster in left field.

The Red Sox have shown that they can slug their way towards a winning streak, and they are one of the better teams in baseball when they catch fire.

The team has other capable slashers as well. Alex Verdugo, Enrique Hernandez, and Christian Vazquez, and Hunter Renfroe have all made their marks. Hernandez at leadoff has been instrumental towards their success.

The secret weapon for Boston should be their southpaw ace, Chris Sale. Sale was dominant from 2012-18 when he was healthy. Injuries mounted, and he struggled in 2019 before ultimately going through Tommy John surgery and just getting back to baseball this summer.

Sale has been vital to the success of the Red Sox, but he was spinning gems back in his early days with the White Sox.

He was seemingly in the Cy Young race every season:

  • 2012 Cy Young Finish: Sixth
  • 2013: Fifth
  • 2014: Third
  • 2015: Fourth
  • 2016: Fifth
  • 2017: Second
  • 2018: Ninth

Sale will look to take the ball for every showdown that revolves around the AL East competition.

Without Sale, the Red Sox would be in jeopardy of missing the postseason despite leading this division for most of the early stages of the summer.

Nathan Eovaldi, Eduardo Rodriguez, and Nick Pivetta would be able to move down a peg on the staff. Most playoff staffs are only three or four deep throughout the postseason, and most use three until the ALCS.

The value on this team has gotten longer throughout the summer due to others improving their records. The Red Sox may not be the most consistent team, but they have proven they can hang with any team in the American League.

Overcoming low preseason expectations has shown what a chaotic season it has been for the team.

At +1500 at the best MLB betting sites, Boston brings the value you would want on a talented roster. The AL East will be a gauntlet, but it will prepare them for the best when October arrives.

The Red Sox’s have the offense to rock any opposing pitcher in the postseason.

Philadelphia Phillies (+2000)

The Phillies have been one of the best teams in baseball since the All-Star break. Their lineup is shaping up with Bryce Harper and J.T. Realmuto picking up the slack.

Harper’s performance in July was what the Phillies needed.

  • July HR: 3
  • July RBI: 15
  • July OBP: .452
  • July AVG: .333
  • July OPS: 1.023

The power bat that Harper possesses has picked up in August, making the Phillies even more difficult. Rhys Hoskins (thumb) is another batter that will help them hang onto their division lead in the NL East.

Towards the end of July, the Phillies needed to make some pitching moves to help balance their offense. They added Texas Rangers ace Kyle Gibson, who is an innings eater.

Throw in closer Ian Kennedy the Phillies acquired from the Rangers, and their bullpen is no longer disastrous.

The struggles that the Braves and Mets have gone through are also a benefit for Philadelphia.

New York (NL) had one of its classic collapses, at the end of July/early August. The team lost nine of 11 games and saw their four-game lead evaporate. The Mets are now in jeopardy of finishing several games behind the Phillies.

If that isn’t momentum, I don’t know what is. The Phillies are playing their best stretch of the season, and their main competition is plummeting.

My Top Sleeper – Toronto Blue Jays (+1600)

This giant killer of a franchise with their current build is the best 2021 World Series sleeper pick.

The youngsters can rake with the best of them and are battle-tested. Having played in the AL East this entire season has helped.

Vladimir Guerrero Jr. is among the best bets to win the 2021 AL MVP, and he has been crushing the ball in 2021.

Check out his stats.

  • .311 batting average
  • .406 OBP
  • .617 slugging %
  • 35 home runs
  • 87 runs
  • 88 RBI

The pitching is an underrated part of the team. The Jay’s acquisition of Jose Berrios youthful arm has been pleasant thus far. Pitcher Robbie Ray has been the ace the entire season, allowing everybody else to ease into the rotation. And, Alex Manoah has been fabulous thus far as a rookie.

Steven Matz and Hyun Jin Ryu round out the pitching line-up and have flashed as southpaws.

The Blue Jays have been tough to keep off the scoreboard due to their ability to crush mistake pitches. Every inning brings a new scoring threat, especially since there are no easy outs in the lineup.

Take the Blue Jays as your top sleeper to win the World Series. The value is too good to pass up.

Betting on 2021 World Series Sleepers

These 2021 World Series sleepers are all worth wagering on due to the value they possess.

The Padres and Red Sox are trendy teams with potent everyday lineups that can put it on the opposition. The top end of their rotations has postseason experience, and they each have the goods to deliver.

The Phillies bring the most intrigue since they have the longest odds. If you risked $100 on the Phillies, they would give you $2000 if they end up winning it all. Zack Wheeler, Aaron Nola, and Kyle Gibson are a nasty top end of a rotation. Philadelphia brings value, and it may shorten if their competition continues to slide.

The selection to watch out for is Toronto. The AL East does not automatically put them deep into October, but the roster is there for some magic.

The top of the Blue Jays order is lethal. George Springer, Marcus Semien, Bo Bichette, and Vlad Guerrero Jr. have the offensive ability. They all have the pop to take the opposition yard on any pitch, but there are no easy outs in the lineup.

Pitch counts will build in the postseason after a few innings, and starters will get pulled. The value is perfect for a sleeper like the Blue Jays, so be sure to jump on this squad before the odds shorten up.

For more great picks, odds, and analysis, check out our sports betting picks page.



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