Phillies vs Cubs Predictions, Picks, Odds: Castellanos Still Loves the Friendly Confines

Nick Castellanos has been a major proponent for the Phillies' offense during the club's recent hot streak. He also loves to hit at Wrigley, dating back to his brief tenure with the Cubs. His TB prop against a pitch-to-contact Kyle Hendricks is the play.

Rohit Ponnaiya - Betting Analyst at Covers.com
Rohit Ponnaiya • Betting Analyst
Jun 29, 2023 • 09:37 ET • 4 min read
Nick Castellanos Philadelphia Phillies MLB
Photo By - USA TODAY Sports

The Philadelphia Phillies and Chicago Cubs wrap up a three-game series at Wrigley Field tonight. The Phillies won the first two games in this series and have been red-hot lately, going 17-5 in their last 22 games.

MLB betting odds opened with this showdown at close to a pick'em with the Phillies installed as slim -115 road favorites. Here are my best free MLB picks and predictions for Phillies vs. Cubs on June 29.

Phillies vs Cubs odds

Phillies vs Cubs predictions

The Phillies have been on fire in June and outfielder Nick Castellanos has been a big reason why. Castellanos went 2-for-5 at the plate with a home run and double last night and he's slashing .371/.408/.607 in 22 games this month. 

The Cubs are sending Kyle Hendricks to the hill today and while the veteran has a sparkling 2.60 ERA in six starts, there are some concerning analytics behind that number. His expected ERA sits at just 4.17 and his expected weighted on-base average (xWOBA) of .320 is significantly higher than his wOBA of .239. This is a starter who has seen his play decline significantly over the last couple of years and while he doesn't get hit hard, he also allows a decent amount of contact.

Castellanos has gone 5-for-16 against Hendricks in his career and has also excelled at Wrigley Field, where he has an incredible .725 slugging percentage in 45 games.

With Castellanos projected to get between 1.9 and 2.3 total bases according to most models, bet the Over 1.5 total bases at plus money. 

My best betNick Castellanos Over 1.5 total bases (+115)

Phillies vs Cubs same-game parlay

Nick Castellanos Over 1.5 total bases (+115)

Under 8.5 (+145)

Taijuan Walker Over 4.5 strikeouts (-110)

Taking the Over on Castellanos' total bases combined with the Under 8.5 runs makes for a good multiplier. And even if Castellanos and the Phillies have success against Hendricks, there's still a good chance that we'll see fewer than nine runs in this game. After all, Phillies starter Taijuan Walker has been red-hot this month while the Cubs are just 22nd in the majors in OPS (.688) in June.

Walker has a 1.50 ERA with a 0.83 WHIP and an OBA of .154 through 30 innings this month. He has also fanned at least five batters in each of his last four starts and is averaging 6.5 strikeouts per start over that span. 

Learn how to bet a same-game parlay with these helpful tips and strategies.

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Phillies vs Cubs moneyline and Over/Under analysis

The Phillies won 8-5 last night to improve their record to 42-37. Walker was inconsistent at the start of the season but has looked very sharp lately and Philadelphia has gone 11-3 in his last 14 starts. 

There are some worrying underlying numbers for Hendricks but he has looked good lately and the Cubs have gone 4-1 in his last five starts.

The close line in this matchup also makes sense because both teams are so similar in terms of production at the plate. The Phillies are 13th in the majors in wOBA (.321) while the Cubs are 14th (.320), and only one spot separates them in hard-hit rate as well. 

Aaron Nola and Drew Smyly were lit up last night with 12 runs scored through the first five innings. That might be a big reason why the Over opened at 9 but has ticked up to 10 (albeit juiced to the Under at about -120) as of 9 a.m. ET.

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Trend to know

The Phillies are 10-1 in their last 11 games on the road. Find more MLB betting trends for Phillies vs. Cubs

Phillies vs Cubs game info

Location: Wrigley Field, Chicago, IL
Date: Thursday, June 29, 2023
First pitch: 8:05 p.m. ET
TV: MLB Network

Starting pitchers

Taijuan Walker (8-3, 4.10 ERA): Walker went 12-5 with a 3.49 ERA and a 1.20 WHIP with the Mets last year. He had an ugly 6.53 ERA through his first nine starts this season but has a 1.71 ERA in seven starts since. That span began with a stellar outing against the Cubs on May 21 when he allowed just two hits through 5 1/3 innings of shutout ball. 

Kyle Hendricks (3-2, 2.60 ERA): Hendricks posted a 3.00 ERA with a 1.09 WHIP in 130 starts between 2016 and 2020. Over the last two seasons, his ERA soared to 4.78 while his WHIP rose to 1.33, but he seems to be back on track this year. Hendricks began the season on the IL but has looked very sharp since returning to the rotation at the end of May. In six starts, he has a 3.56 FIP with a 0.98 WHIP and an OBA of .197.

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With a background playing soccer, rugby, and boxing, combined with a journalism degree, it's little surprise that Rohit gravitated towards the world of sports betting. He specializes in betting on UFC and college basketball, two sports where the eyeball test can tell you a lot more about matchups than any analytics. Rohit has years of experience handicapping NFL and NBA games as well as niche betting markets such as politics and Oscar odds. He's also the resident CFL expert and formerly hosted "The Chez and Ro Show" with former CFL star Davis Sanchez.

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