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White Sox vs. Red Sox MLB picks: Luis Castillo's Chicago debut might not be successful Thursday

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If the Chicago White Sox and Boston Red Sox meet again in 2026 after tonight's series finale from Fenway Park, it would be in the American League playoffs. And it's looking more and more likely each will get there. Both clubs were big buyers ahead of the trade deadline, and the Pale Hose's top acquisition in starting pitcher Luis Castillo makes his debut in this one. It's a 7:10 ET first pitch.

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The White Sox front office settled for Castillo (3-9, 5.06 ERA), who is under contract through next season and didn't cost the  team any of its top prospects. All it did was cost money, really, as Chicago will pick up the portion of the $22.75 million owed in 2026 and the $22.75 million for '27, with roughly $30 million guaranteed.

Needless to say, Castillo's numbers are not great on the surface, but the 33-year-old three-time All-Star has been durable in his 10-season career (with a 3.65 ERA), has playoff experience and is considered a terrific locker-room guy. He's just what a young team needed. At worst, Castillo should eat innings and help an overworked bullpen. And he has been better of late with a 3.88 ERA over his final 10 games with Seatle, which gave him three runs or fewer of support 15 times this season. The White Sox have a significantly better offense than the Mariners.

"We're at the bottom of the league in regards to starting pitching innings. And so to be able to insert someone that pitches as regularly, posts as often as Luis Castillo, has the credibility into this group, we felt like it is going to make a meaningful step in the right direction," GM Chris Getz said following the deal. "Someone that can help lead this young pitching staff, not only cover innings, but has experience pitching in the playoffs."

White Sox-Red Sox MLB same-game parlay

  • Boston money line
  • Alt Under 6.5 F5 total runs

FanDuel: SGP price: +106

Castillo last pitched on July 28 at the Dodgers and allowed five runs and 11 hits over five innings in a no-decision, but trade rumors were swirling, so maybe Castillo wasn't 100% focused. And there's no shame in getting lit up by the Dodgers. Homers have been a problem of late, as he has allowed seven over his past three starts.

Castillo faced the Red Sox in Seattle on June 19 and took a no-decision, allowing four earned runs over four innings. The SportsLine Projection Model has Castillo at 5.8 innings, 5.0 strikeouts, 5.0 hits allowed and 2.3 earned runs. Castillo might get one break tonight, as Boston All-Star slugger Willson Contreras left Wednesday's early with an illness.

I'm not sure the seeding will work out for a Red Sox-White Sox playoff series, at least in the wild card round. Chicago has a three-game lead atop the AL Central and is the +220 favorite to be the AL's No. 2 overall seed. That would mean a first-round bye. Boston is the +150 favorite to be the No. 5 seed, which means the second wild card team. And that club visits the top WC team, currently the Yankees (+135 favorites to finish as the No. 4).

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No team in the majors has been better than the Red Sox (62-51) since July 3 as they are 25-3 since then and enter on a seven-game winning streak. Back then, it looked like interim manager Chad Tracy would be just that, but now he's +350 third favorite for AL Manager of the Year, with the favorite the White Sox's Will Venable (-140).

While Boston added plenty ahead of the deadline, the big offseason acquisition via free agency was lefty Ranger Suarez, and that has worked out pretty well and he starts tonight. Suarez (4-3, 3.15 ERA) has made two starts since a stint on the injured list with a groin strain and has yet to go a full five in either on a pitch count of about 65.

That pitch count should go up tonight, although I wouldn't go expecting seven innings, and the model projects him at 5.4 innings, 5.4 strikeouts, 4.8 hits allowed and 2.0 earned runs. Suarez hasn't faced the White Sox this year. 

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With Contreras potentially out, that should help in regard to that first five alternate total, and I do think Castillo will be better with his new club now that he's considered a No. 1 guy in Chicago whereas he was about No. 6 in Seattle. But I still think Boston wins, and so does the model. Check out other expert picks in the SportsLine daily newsletter.

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