The Windup: Starkville | Jon "Boog" Sciambi on the Cubs’ Breakout Season

Hosted by Doug Glanville (filling in for Jayson Stark), with guest Jon “Boog” Sciambi | September 3, 2025

Overview

This episode of The Windup’s “Starkville” dives into the Chicago Cubs’ impressive breakout season with Jon “Boog” Sciambi, the team’s broadcaster and long-time baseball voice. With Jayson Stark on vacation, Doug Glanville hosts, covering recent wild plays, the art and analytics of building a contender, roster strategies as September arrives, and in-depth Cubs talk—focusing on the blend of youth, defense, and a high-IQ clubhouse.

Key Discussion Points & Insights

1. Around the League: Philadelphia, Milwaukee, and Cleveland ([01:40]–[09:33])

• Doug recaps his recent travels: A wild game in Philadelphia (highlighting Braves sensational rookie catcher Drake Baldwin’s home run), followed by Milwaukee, where he’s impressed with the Brewers’ discipline, run differential, and power despite their lack of household names.
• A unique Red Sox-Guardians play at Pesky Pole:
  • Doug describes an odd Trevor Story homer where the ball glanced off the right fielder’s glove, ricocheted off the Pesky Pole, then deflected into a kid—ending with Story in limbo until replay ruled the play a home run. ([06:03])
  • Memorable quote: “Interrupted glory. That should be a term, the I.G.—you’re interrupting glory…why are you going to wait at second base for 10 minutes?...But, you know, don't interrupt the celebration. Just let. Let them play. Let them have fun.” — Doug Glanville ([07:22])

2. Jon “Boog” Sciambi on the Cubs’ Rise ([09:33]–[16:00])

• Sciambi’s tenure and expectations:
  • Entering his fifth year with the Cubs, he admits this is “certainly been the most fun” and attributes their breakout to an unexpectedly potent offense and a balanced, athletic roster.
  • “I thought they were going to be good… But I thought they’d be pretty good… I don’t think I saw it coming that they would be quite this good.” — Boog Sciambi ([10:17])
• Craig Counsell’s impact:
  • Both Doug and Boog spotlight how Cubs manager Craig Counsell stresses details, fundamentals, and the day-to-day process.
  • Boog: “The Cubs have a pretty high IQ team. They have the combo of high IQ and they're athletic.” ([11:52])

3. Pete Crow-Armstrong: The Magnetic Centerpiece ([12:37]–[16:00])

• On PCA’s defensive wizardry, base-running, and fan appeal:
  • Despite August struggles at the plate, Boog praises Crow-Armstrong’s energy and defense—already worthy of a Gold Glove, possibly a Platinum.
  • “You can't take your eyes off him…he’s just a special kid. It’s been fun to watch.” — Boog Sciambi ([13:25])
  • Offensively, PCA’s switch to targeting “pull in the air” power has driven surprising slugging numbers.

4. Roster Construction & Young Player Development ([17:24]–[20:49])

• Modern approach to lefty hitters: Doug probes how PCA and fellow rookie Michael Busch are managed—limiting exposure to lefties versus playing through struggles.
  • Boog notes: “Even against lefties, neutralizing Pete at the plate, the value of the defense…is still more than likely going to net you something plus or at least neutral.” ([18:11])
• On the Matt Shaw model:
  • Discussion of giving patience to high-upside rookies who don’t hit right away, as team depth and offense help absorb their growing pains.
  • “I don’t think that the competition level at Triple A is what it used to be…so teams feel like sending a guy to Triple A isn’t helping all that much.” — Boog Sciambi ([20:49])

5. Trade Deadline Philosophy & Analytics Critique ([23:13]–[30:01])

• Deadline conservatism and risk aversion:
  • Boog voices frustration about the lack of “challenge trades” and a general risk-averse approach by analytics departments.
  • “All these smart guys…hoard prospects…and behave so conservatively. What I’d really like is at the deadline—go figure out how you can find a way in a small sample to improve your odds, because that'll make this way more interesting.” ([23:48])
  • “I think that they lose sight of the idea that the goal is to win the World Series…taking those risks…will make it way more interesting.” — Boog Sciambi ([23:48])
  • Doug adds that expanded wildcards have created more buyers but not more action, instead leading to “a staring contest.” ([28:38])

6. September Strategies: The Playoff Push ([32:03]–[35:16])

• Roster limits and new call-up culture:
  • Both reminisce about the old days of massive September call-ups, contrasting today’s capped influx. Doug laments the loss of camaraderie and little rewards for minor league success.
  • Tactical focus: Boog says teams are now “just looking for every possible scenario where you can collect outs”—especially in bullpens. ([33:00])

7. “State of the Game” Reflections ([35:16]–[42:10])

• More prospects, but more learning in MLB: Players “are not polished, are learning at this level.”
• Parity and unpredictability:
  • “I don't think anybody's that good this year is the one thing that…surprises me a bit.” — Boog Sciambi ([35:58])
  • Cites the Brewers' and Rays’ ongoing successes as evidence the sport rewards smart, creative roster construction.
• Needs for the game’s future:
  • More balls put in play, faster pace, and—critically—more media/player access for storytelling and growing the sport.
  • “We need more access… there's just less and less time, the players hide more… they have a responsibility to talk to the media. I just think it's about being accountable.” — Boog Sciambi ([35:58])

8. Rule Tweaks, Replay, and Unintended Consequences ([40:01]–[42:10])

• Applaud rule improvements like the new running lane, but both call for eliminating random, illogical rules and refining replay—particularly tags where a runner pops off the base for a split second.
  • “That is not what the point of replay was—that a guy pops off the base after being safe…that’s not the point of replay.” — Boog Sciambi ([41:36])

9. Playoff Race Outlook ([42:10]–[43:01])

• Boog’s focus down the stretch: Excited for potentially dramatic wild card matchups (Yankees, Red Sox, Mets, Dodgers, Cubs, Padres) and a wide-open National League West.
  • “It’s just going to be fun because it seems like there’s a lot of parity and it’s pretty balanced out.” ([42:20])

10. Dugout Plus: Remembering Massive Call-Ups ([43:23]–[49:34])

• Doug pays tribute to the culture and emotion around September’s old mega-roster expansions, celebrating how minor league lifers could “get a taste of the big leagues” and often do it together.
  • “I always thought that was cool—to get called up with a group and have that shot…Now, it’s capped. Of course it’s great for those players, but…it was nice when you could call up a group en masse.” ([43:23])

Notable Quotes

• Doug Glanville:

  • “That should be a term, the I.G.—you’re interrupting glory.” ([07:22])
  • “It was nice to celebrate together…go up from Triple-A and you’re just like, yeah!” ([43:23])

• Jon “Boog” Sciambi:

  • “You can't take your eyes off him…he’s just a special kid. It’s been fun to watch.” (On Pete Crow-Armstrong, [13:25])
  • “I don’t think I saw it coming that they would be quite this good.” (On Cubs, [10:17])
  • “All these smart guys…hoard prospects…and behave so conservatively.…I think that they lose sight of the idea that the goal is to win the World Series.” ([23:48])
  • “There's a ton of talent…you're seeing players who are not polished, who are learning at this level.” ([35:58])

Timestamps for Important Segments

• [01:40] Doug recaps Phillies-Braves, Drake Baldwin’s emergence
• [06:03] Pesky Pole oddity—instant replay/home run drama
• [09:33] Jon “Boog” Sciambi joins—Cubs’ surprise season story
• [11:52] The Counsell touch: IQ, defense, and athleticism
• [13:25] Pete Crow-Armstrong deep dive—defense, magnetism
• [18:11] Rookie lefties and managing platoons
• [20:49] Triple-A’s diminishing developmental value
• [23:13] Trade deadline—analytics and risk aversion rants
• [32:03] September, the playoff push, and roster tricks
• [35:16] State of the game; what’s working, what worries
• [40:01] Rule talk: running lanes, instant replay fixes
• [42:10] What Boog’s watching as races heat up
• [43:23] Dugout Plus: remembering big group call-ups

Tone & Style

The conversation is lively, candid, a bit playful but always serious about the game’s details. Both Glanville and Sciambi blend insight with storytelling, nostalgia, and a willingness to critique where necessary—all in a way designed for both statheads and old-school fans.

For Listeners Who Missed the Episode

This episode provides a thorough analysis of why the Cubs surged in 2025, how modern baseball manages its roster and prospects, the strengths (and quirks) of the game as it enters September, and what both on-field and off-field changes could keep baseball growing. With a warm, relatable tone, Doug and Boog deliver behind-the-scenes insight, memorable moments, and some classic baseball storytelling—making it a must-listen for fans curious about the Cubs, baseball’s future, and the soul of the sport.