Just about everyone knows someone in their life who is a bit technologically challenged. And for Cubs broadcasters Jon “Boog” Sciambi and Taylor McGregor, that friend just so happens to be their colleague, Cubs color analyst Jim Deshaies.
Sciambi, McGregor, and Deshaies made up the Cubs’ broadcast team in their matchup against the St. Louis Cardinals on Tuesday night. If you were curious how the three-person dynamic was throughout the game, McGregor showed a hilarious behind-the-scenes video that was not on the Marquee Sports Network broadcast.
Attempting to take a selfie of the three during the game, Jim Deshaies manned McGregor’s phone. The only problem is that McGregor’s phone gave Deshaies fits as he figured out how to take the picture, constantly closing the phone app by accident.
“Here, open it back up,” Deshaies told McGregor. “Why can’t I hit this button over here? What if I did this? Where is the button now?”
As Deshaies continued to fumble with the phone, Sciambi quickly grew irritated with Deshaies’ incompetence.
“Oh my god,” said Sciambi. “JD, I have never said this to you. But I hate you right now.”
Just as it looked like Deshaies had gotten things under control for a selfie, he clicked the wrong button again, which drew another exaggerated groan from Sciambi and McGregor.
POV: trying to get your Baby Boomer coworker to take the group selfie 😂☠️ pic.twitter.com/slddDYUDHU
— Taylor McGregor (@Taylor_McGregor) June 25, 2025
“Oh my god!” said Sciambi.
“Fix it again,” Deshaies said to McGregor. “I can’t do it. I gotta hit the… Tell me again, this button right here? Right there, right?
“Just tap the center thing, for f*ck sake!” added Sciambi.
At long last, Deshaies was finally able to take the selfie after over a minute of attempts gone wrong. But by the time he ultimately figured it out, Sciambi and McGregor were laughing so hard that they were visibly tearing up.
To be fair to Deshaies, he is the oldest person in that booth by a wide margin. So you could argue that he was set up to fail here by being the one to take the photo in the first place.
Either way, it’s probably been quite a long time since Sciambi and McGregor laughed that hard inside a broadcast booth. So, for better or worse, at least Deshaies can take the credit for giving them a moment they won’t soon forget.
About Reice Shipley
Reice Shipley is a staff writer for Comeback Media that graduated from Ithaca College with a degree in Sports Media. He previously worked at Barrett Sports Media and is a fan of all things Syracuse sports.