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Come Fan with UsThursday, June 25, 2026

A Seven-Hour Conversation With Jim Caldwell

Imagine a seven-hour conversation. It’s an entire workday dedicated to speaking to one person; three and a half My Dinner With Andres; an epic dialogue requiring a pair of tireless, well-read raconteurs and, ideally, a six-course meal and an entire bottle of Pappy Van Winkle’s Family Reserve 23-year-old bourbon.

Ryan Grigson, the Colts' new GM, reportedly had a seven-hour "chat" with coach Jim Caldwell before firing him. Yes, Jim Caldwell. This Jim Caldwell:

Caldwell-face_medium

SEVEN HOURS with Jim Caldwell. How did it go? We can only imagine:

0:01

RYAN GRIGSON: Hi, Jim. Thanks for meeting with me today. Obviously, I’m new to the organization, but before I make any personnel decisions, I thought we should sit down and talk about the future of the franchise, see if we share a vision.

JIM CALDWELL: /blinks

GRIGSON: I mean, 2-14 is a rough season, but I’m feeling “lucky”! How about you?

CALDWELL: /closes eyes

/keeps eyes closed

GRIGSON: Lucky? Andrew Luck? New franchise quarterback?

CALDWELL: /snores gently

0:37

GRIGSON: Let’s try some word association! “Championship.”

CALDWELL: Butternut.

GRIGSON: Manning.

CALDWELL: Glazed.

GRIGSON: Dallas Clark.

CALDWELL: Butternut.

GRIGSON: Rebuilding.

CALDWELL: Butternut.

GRIGSON: New boss.

CALDWELL: Glazed.

1:26

CALDWELL: ...Glazed.

GRIGSON: Seriously? Your response to “hot oiled sex with Carla Bruni” is “Glazed”?

CALDWELL: Glazed.

GRIGSON: Jesus.

CALDWELL: Butternut.

2:08

Caldwell turns on a karaoke machine. “You’re Gonna Miss My Love” by Lou Rawls comes on. Caldwell sways slightly, and places the mike to his lips, but never sings.

Caldwell-karaoke_medium

2:40

Caldwell pulls a mass of paper clips and used staples from his pocket, lays them on the table, and begins to separate them into two piles.

3:01

Caldwell turns off the karaoke machine.

3:13

GRIGSON: ...and that’s why, in this competitive market, we have to value players for what they are, not what they were or can be.

CALDWELL: Tato skins.

GRIGSON: Sorry, what?

CALDWELL: Wanna order some potato skins?

4:15

Jim Irsay checks in on the conversation. Caldwell spends the next half hour trying to hold his breath for a minute at a time without telling either Grigson or Irsay.

4:53

CALDWELL: /tries to tie cherry stem with tongue

/accidentally swallows it

/tries to tie cherry stem with tongue

/accidentally swallows it

/tries to tie cherry stem with tongue

/accidentally swallows it

/tries to tie cherry stem with tongue

/accidentally swallows it

Cherry-stems_medium

5:27

GRIGSON: And it’s not just at quarterback where we have that conundrum. We need to upgrade several other skill positions, starting with running back.

CALDWELL: /tries to tie cherry stem with tongue

/accidentally swallows it

5:50

Grigson jabs a pin into Caldwell’s fingers to elicit a response. Over the course of next seven seconds, Caldwell blinks.

6:22

CALDWELL: An egg will cook on human flesh if you let it sit there long enough.

/cracks egg on palm

/stares

6:54

GRIGSON: I’ve got some bad news, Jim. Your entire family has been murdered. Real grisly stuff, too. Entrails everywhere. Their deaths were drawn out and agonizing. Like this conversation, but way bloodier.

CALDWELL: Sorry, what? I ate a lot of cherry stems.

GRIGSON: Your wife and children are all dead.

CALDWELL: ...

GRIGSON: Nah, just kidding!

CALDWELL: ...

GRIGSON: But for reals, you’re fired.

CALDWELL: ...

GRIGSON: We’re going to need that headset back.

Caldwell-stare_medium

CALDWELL: You gonna finish those stems?

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