Episode 64: Red Sox - Red Sox Acquire Sonny Gray From St. Louis Cardinals

In this episode of Red Sox Digest, Jim and Nick dive head-first into the chaos surrounding the Red Sox acquiring Sonny Gray—a move that somehow managed to excite everyone and infuriate everyone at the same time (classic Boston). Jim opens the show with a meltdown worthy of a toddler seeing mall-Santa for the first time, ripping apart the Cardinals’ NyQuil-signed contract structure and questioning why this team can’t stop collecting 35-year-old pitchers like lawn ornaments.

Nick plays therapist for the first 10 minutes before unleashing his own rant: Gray is fine… as long as he’s not your No. 2. Together they break down the trade details, the $20 million in Cardinals guilt-money, Gray’s hideous Fenway/Yankee Stadium career numbers, and the bigger fear: that Craig Breslow is about to tell fans, “We’re good,” and walk away from free agency like it’s a clearance rack.

From there, they tear into:

• The rotation depth chart that looks like a horror movie

• The Bregman Instagram bait (and why opt-outs should be thrown into the ocean)

• Whether the Sox will finally stop treating free agents like they’re made of plutonium

• And a surprise twist: a genuine push for JT Realmuto

• Plus early holiday wishes for Pete Alonso in a bow under the tree.

The show closes with both hosts agreeing on one thing: this offseason needs at least two bats and one more legit starter—or the pitchforks are coming out.

1. Sonny Gray Trade Breakdown

• Red Sox receive Sonny Gray + $20M

• Cardinals receive Richard Fitz, Brandon Clark, PTBNL/cash

• Gray’s contract reworked: $31M for 2026 + $10M buyout

• Essentially: Sox pay ~$20M, Cards pay ~$20M

• Gray getting $41M for one year, more than Judge made last season

• Jim’s reaction: “A used limo with disco lights missing.”

• Nick’s reaction: “Fine… AS LONG AS HE’S A #3.”

2. Pros & Cons of Sonny Gray

Pros:

• Durable: 180+ innings, 200+ Ks

• Better option than Giolito/Buehler 2025 retreads

• Can stabilize rotation if not relied on as a co-ace

Cons:

• 36 years old

• One-year rental

• Horrific Fenway numbers (0–4, 6.84 ERA)

• Horrific Yankee Stadium numbers

• Zero high-leverage track record outside NY disaster

3. Organizational Fear: Stopgap Hell

• Boston has lived on one-year pitchers for years

• Jim: “Stop giving up prospect capital for 35-year-old rental arms”

• Nick: “If this is the big move, I’m rioting.”

4. Rotation Concerns

• Media graphic showing:
  Crochet – Gray – Bello – Crawford – Sandoval

• Hosts absolutely torch the idea

• Crawford and Sandoval likely not ready

• Young depth (Tully/Early/Dobbins) only existed last year due to injuries

• Jim: “This is Chris Sale injury timing all over again—but without Chris Sale’s talent.”

5. The Big Moves Boston Should Make

• Nick’s wishlist: Skubal or Joe Ryan

• Jim: prefers Ryan and Gray if possible

• Both: Crochet needs a REAL #2 in front of Gray

6. Bregman Drama (Instagram + Opt-Out Rant)

• Bregman’s IG shows him in a Red Sox jersey again

• Does it mean anything? Maybe… maybe not.

• Jim absolutely unloads on opt-outs

• Both agree:

  • If Bregman returns, it can’t be alone

  • If he doesn’t return, Sox still need TWO bats

  • Boris is milking this thing dry

7. Pete Alonso Wish List

• Both want him

• Both need him

• Both are begging Santa/Breslow/anyone to drop him at Fenway

• Alonso + one more bat is the minimum acceptable outcome

8. JT Realmuto Curveball

• Rumor surfaces

• Nick: “Whatever it takes. Wong/Navarez can go.”

• Jim: “If acquiring JT helps parlay a trade for a top starter… do it.”

9. Final Consensus

• Sonny Gray = acceptable piece

• Sonny Gray as the only piece = disaster

• Red Sox need:
  +1 ace/co-ace
  +2 impact bats

• Anything less = another year of mediocrity