History will be made in the next two weeks.
Neither the Tampa Bay Rays nor the Milwaukee Brewers has ever won a World Series before, but one of these teams will finally break that streak at the end of this World Series. It’s been a longer wait for the Brewers; Tampa Bay is playing in the Fall Classic for the first time since 2020, and Milwaukee reached its only World Series in 1982.
Game 1 of this World Series is set to begin at 8 p.m. ET at American Family Field, not too far from the shores of Lake Michigan.
The Brewers are -192 favorites at DraftKings Sportsbook to open up a 1-0 lead with likely National League Cy Young Award winner Jacob Misiorowski set to take the mound. The Rays (+158) have a Cy Young candidate of their own in Drew Rasmussen, but they’re opting for Nick Martinez instead.
Below, I’ll break down my favorite prop bets from tonight’s much-anticipated matchup, focusing on one player from each team.
Rays at Brewers Best Prop Bets Tonight for Friday 10/23/26
Jacob Misiorowski O16.5 Outs Recorded (-103)
Misiorowski hasn’t had the greatest postseason so far, as he lasted just four innings against the San Diego Padres in the NLDS and 4.1 against the Los Angeles Dodgers in the NLCS. In each circumstance, the opponent managed to get his pitch count up, as he threw 88 pitches against the Padres and 94 against the Dodgers, issuing three walks in the latter start. Still, despite recording 16 or fewer outs in each of his last five starts combined between the regular season and the playoffs, he did so in 18 of his 30 regular season starts despite averaging just 88.2 pitches per game.
Unlike Los Angeles and San Diego, who swing relatively infrequently and, especially in the latter’s case, whiff a lot, Tampa Bay employs a relatively aggressive plate approach. The Rays swung at about a league-average rate and had a whiff rate 1.5 percentage points lower than any other team, so they faced the second-fewest pitches per plate appearance. Misiorowski should be able to mow through Tampa Bay’s offense quickly as long as his fielders are making plays behind him, and Milwaukee ranked fourth in Defensive Runs Saved. Misiorowski’s completing the sixth inning, as he did in his lone regular season start against the Rays, would allow Pat Murphy to save one of DL Hall, Aaron Ashby, Abner Uribe, and Trevor Megill to pitch in Game 2 with a fresh arm.
Chandler Simpson 2+ Hits + Runs + Stolen Bases (+116)
The problem with choosing one player from each team is that I have to choose either Martinez against one of baseball’s hottest offenses or any batter to get to Misiorowski, but I like Simpson, an old-school player who very nearly won the AL batting title this season. The 25-year-old had a strong ALCS, slashing .294/.316/.476 with two stolen bases, and he had at least two combined H/R/SB in three of his five starts. Simpson also had an excellent finish to the regular season, batting .344 and scoring 27 runs after the All-Star break.
Misiorowski’s velocity might actually work in Simpson’s favor. Despite an xBA of just .270 against such pitches, Simpson batted .350 against right-handed four-seamers, largely because his blazing speed turns outs for most batters into hits. He slaps a lot of grounders down the third-base line, a hit type that Misiorowski is elite at inducing. It’s not hard to imagine Simpson hitting a dribbler and out-running David Hamilton’s throw. Once he’s on base, only a subpar jump can stop him from getting a steal, as he led the American League in that stat. Tampa Bay ranks second among playoff participants in RBI’s with runners in scoring position.
