Skip to main content
Come Fan with UsMonday, June 22, 2026

Theo Epstein And The Most Awkward Business Meeting Of All Time

On Monday, Theo Epstein, the new Cubs’ President of Baseball Operations, held a meeting-ish activity over lunch to get familiar with his co-workers. There is no way that this was not the most awkward thing ever.

Epstein, who will be introduced to the media on Tuesday, then asked each person to sing their college fight song. After everyone was through with their attempts, Epstein, a Yale graduate, got up on a chair and sang his own, according to sources.

I’ve received reports (from myself because I completely made them up) that this was only the first item in Epstein’s itinerary for his super-awkward business meeting. Here is the rest of it:

  • 12:05 p.m.: Have everyone sing the fight song of their alma mater.
  • 12:09: Stand on chair and sing fight song of own alma mater.
  • 12:10: Continue to stand on chair and do nothing.
  • 12:14: Announce that I am "a space person."
  • 12:18: Continue to stand on the chair until a leg snaps and I fall over.
  • 12:20: Clarify that I was just kidding about being a space person.
  • 12:21: Drum fingers on table as rapidly as possible. Grit teeth. For a really long time.
  • 12:51: Ask everyone which baseball is their favorite. If someone actually has a good answer for this, such as an autographed ball or a foul ball they caught, frown as hard as possible.
  • 12:57: Point out that "Cubs" is an anagram of "Bucs," the shortened name of that football team. Ask everyone to rate how neat that is on a scale of 1 to 10. Inform the person who gives the lowest score that he or she is fired. Also, fire anyone who gives it a 10, because it isn't exactly "lid of soup thermos also serves as a bowl" neat.
  • 12:59: Flag down server. Ask for "a McDonald's burger" while attempting to stifle hysterical laughter.
  • 1:02: Announce my plans to buy the Cubby Bear, raze the site, and build a 100-foot statue of Brant Brown handing an apple to Josef Stalin.
  • 1:03: Claim that I am just joking about this, too. Tell a childhood anecdote about a time I found a plank of wood that has nothing to do with anything.
  • 1:05: Hold a fork and glass of water in my hand. Ask everyone the following question: "would you rather have exactly one glass of water a day for the rest of your life, or have an unlimited supply, the catch being that you had to get it into your mouth using only a fork?"
  • 1:08: Wait until everyone, surprised at themselves, begins to chuckle at the idea and discuss it amongst themselves, and then begin shrieking as loudly as possible until everyone falls silent.
  • 1:09 While still shrieking, sing the theme song from TBS' Braves broadcasts from 1991. Identify which direction is north, and run directly at it until I run full-speed into something. Let everyone else figure out that the meeting is over.
  • 1:16 Sit alone for a few minutes before eventually calling for pizza from another restaurant.

(Link via Over the Monster)

See More:

More in General

GeneralFromPosting and Toasting
An SB Nation New Yorker needs our helpAn SB Nation New Yorker needs our help
GeneralFromPosting and Toasting
General
Sabastian Sawe breaks 2-hour barrier, shatters marathon world recordSabastian Sawe breaks 2-hour barrier, shatters marathon world record
General

The mythical two-hour mark was broken at the London Marathon.

By Bernd Buchmasser
A Huge Dog
THE HISTORY OF CHARGING THE MOUND, EPISODE 1THE HISTORY OF CHARGING THE MOUND, EPISODE 1
Play
General
Super Bowl 60 coin toss resultsSuper Bowl 60 coin toss results
General

The Seahawks and Patriots will open the Super Bowl with the coin toss to determine who starts with the ball. We have the full coin toss results for Super Bowl 60.

By David Fucillo
General
Marc Marquez completes a comeback for the agesMarc Marquez completes a comeback for the ages
General

MotoGP’s Marc Marquez completed a comeback for the ages with his 2025 title

By Mark Schofield
General
How to make sure SBNation.com appears in your Google search resultsHow to make sure SBNation.com appears in your Google search results