MLB Friday mega parlay (+1118 odds) today 9/23: Aaron Judge eyes 61, but Red Sox aim for upset

Red Sox hitters Devers, Bogaerts, Pham
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Since graduating from Davidson (The College That Stephen Curry Built), I have been writing about sports -- just about any and all you can think of! -- and coaching tennis in Atlanta, GA. Beyond the four major sports, I am an avid tennis fan and cover the ATP Tour on a daily basis. If I'm not busy writing, you can generally find me on a tennis court or traveling the world wherever a sporting event takes me. For Ricky Dimon media enquiries, please email
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We are getting the Major League Baseball weekend started with a full 15-game slate on Friday night. The Boston Red Sox and New York Yankees are continuing a 4-game series, with first pitch of their showdown set for 7:05 pm ET on Apple TV+. Another Apple TV+ game has the St. Louis Cardinals and Los Angeles Dodgers wrapping up the schedule at 10:10 pm ET. In a National League East battle between one definite playoff team and one hopeful playoff team, the Atlanta Braves are going up against the Philadelphia Phillies at 7:05 pm ET on ESPN+.

For this parlay we are going with two plays on the money line and one favorite on the run line. Let’s break down each of the three legs one by one.

Chicago Cubs ML over Pittsburgh Pirates (-110)

There’s no real ace on the mound for either NL Central team today; there’s also no real depth to either lineup. Therefore, it’s no surprise that this contest is relatively evenly priced. The Cubs should be able to take advantage of a Pirates team that just gave up a bunch of runs to the Yankees in back-to-back games. Obviously the Cubs aren’t the Yankees, but Pittsburgh’s bullpen is already the worst in the league and the fatigue is probably going to catch up with the relievers. Chicago is also being a bit undervalued due to having a rookie starting this game. However, Javier Assad proved he wasn’t intimidated by the bright lights right from the jump. His MLB debut was a shutout win over a stout Cardinals lineup.

He even followed that up by holding the Blue Jays scoreless and also held the Mets to only 1 run in 6.0 innings 2 starts ago. Meanwhile, Pirates starter Bryse Wilson has allowed 11 runs in his 3 starts this month and Pittsburgh has lost 4 of his last 5 appearances.

Check out our Cubs vs Pirates preview

Boston Red Sox ML over New York Yankees (+190)

All eyes will be on Aaron Judge this weekend, and understandably so as he attempts to tie and ultimately surpass Roger Maris’ single-season AL home-run record that has stood for 61 years. However, there is still a game to be played and with that comes betting value. The value today is on Boston. At 42 years old, Rich Hill is on his third go-around with the Red Sox. Obviously he isn’t in his prime, but he has been serviceable in 2022 and the Yankees have not yet seen him this season. That could be at least a little bit of an advantage for the veteran southpaw.

Gerrit Cole is taking the mound for New York and he has not been his usual dominant self this year. Cole’s unspectacular 3.41 ERA has been primarily damaged by the longball. If Boston can take advantage of a mistake or two, an upset could be in the cards.

Check out our Red Sox vs Yankees preview

Los Angeles Dodgers -1.5 over St. Louis Cardinals (+120)

The Cardinals are in a dry spell and the Dodgers have to be the last team that a slumping ballclub would want to face. St. Louis been shut out in 3 of its last 4 games and the only exception has been a 5-run performance. Five runs in 4 games is not going to get it done against any team, needless to say – and especially not against a team that could go down as of one the best in baseball history. The Dodgers, aside from having the best record in baseball, have not deviated; they have been playing great baseball of late with a 10-3 in their last 13 games and a 16-5 mark in their last 21 at home. The Dodgers have scored 46 runs in their last 11, too. L.A. should roll to wrap up Friday night’s MLB schedule.

Check out all of our MLB previews and picks for Friday

Today’s MLB mega parlay (9/23)

Cubs ML (-110)

Red Sox ML (+190)

Dodgers -1.5 (+120)

Parlay odds: +1118

Odds available at time of publishing. 

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