Brewers vs Rays Prop Picks: World Series Game 5

Neil Parker - Analyst at Covers.com
Neil Parker • Betting Analyst 16+ years betting experience
Updated: Oct 28, 2026 , 11:00 AM ET • 4 min read

Milwaukee stars Jacob Misiorowski, Jackson Chourio and William Contreras lead the way to a Game 5 win.

Brewers vs Rays Prop Picks, Milwaukee Brewers, MLB, Jacob Misiorowski, Jackson Chourio, William Contreras
Photo By - Reuters Connect. Custom Image of Milwaukee Brewers teammates Jacob Misiorowski, Jackson Chourio, and William Contreras

The Tampa Bay Rays staved off elimination to extend the World Series to Game 5, and the Milwaukee Brewers are trading as road favorites ahead of tonight's 8 p.m. ET first pitch at Tropicana Field.

My favorite Brewers vs. Rays prop picks and MLB picks for Wednesday, Oct. 28, are headlined by Milwaukee ace Jacob Misiorowski.

Best Brewers vs Rays props

For help understanding probabilities, see our odds calculator.

Pick Probability
 Brewers Jacob Misiorowski Over 15.5 outs 49%
 Brewers Jackson Chourio Over 1.5 total bases 47%
 Brewers William Contreras Over 1.5 hits + runs + RBI 51%
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Prop pick #1: Jacob Misiorowski Over 15.5 outs

Milwaukee Brewers manager Pat Murphy will give ace Jacob Misiorowski his longest leash of the postseason, with the Milwaukee bullpen already up to 21 innings through four games. 

As a result, I recommend this Over prop up to 52%.

Misiorowski has been a touch unlucky this postseason, too. His .361 BABIP is astronomically higher than his career regular-season mark of .255.

I’m also expecting an uptick in strikeouts from the ace, with his 10.3% swinging-strike rate and 25.5% strikeout rate well below his regular-season marks of 17.6% and 37.9%, respectively.

Prop pick #2: Jackson Chourio Over 1.5 total bases

With Brewers star Jackson Chourio primed for statistical correction at the dish, I would target this Over up to 51%.

As good as the 22-year-old outfielder has been with 10 hits during the World Series, his postseason .323 wOBA and .145 ISO are still well below his regular-season marks of .401 xwOBA and .229 xISO.

Chris Hatfield goes a step further, targeting Chourio to go long in his Brewers vs. Rays predictions.

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Prop pick #3: William Contreras Over 1.5 hits + runs + RBI

Even with a 0-for-5 night at the dish in Game 4, Milwaukee catcher William Contreras is 7-for-17 with a run and three RBI during the World Series.

He’s sporting a .454 wOBA for the postseason while hitting in the heart of the lineup, so I recommend this Over up to 55%. Contreras posted a nearly identical .760 OPS against left-handed pitchers and a .756 OPS against righties during the regular season, too.

Neil Parker's 2026 Transparency Record
  • Prop picks: 21-12, +11.58 units
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Neil Parker - Covers
Betting Analyst

Neil Parker is, first and foremost, a sports fan. A huge supporter of the Cowboys, Cubs, and Maple Leafs, he has managed to parlay his passion into writing gigs at some of the top websites in the industry.

Neil takes a numbers-based approach to his handicapping and complements his in-depth statistical analysis with a keen eye on the markets to provide the best available odds. He loves to lean on his rolodex of idioms to offset his inner nerd. When it comes to wagering, he throws down on anything that catches his eye at bet365, Betway and BetVictor. He also keeps a close eye on CoolBet because the polar bear brand often has outlier NHL and NFL moneyline prices.

Neil graduated with honors from St. Thomas University in 2007 before completing his BEd at Acadia University in 2010. After teaching a myriad of courses and subjects, he found a groove delivering fun lessons to exceptional learners in non-traditional classroom environments. If his decade-plus teaching run taught him anything about sports betting, it’s to stay the course and use the summer – or offseason – to refresh and prepare to be better in the year to come.

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