I’m starting to notice a trend with these Lovable Reunion Podcast stories … they’re all about how everyone was basically just drunk all the time. Do with that what you will. Lol.
Anyway, the latest story is another iconic one, this time of Theo Epstein, Jon Lester, and how they landed David Ross on a drunken phone call from a bar at 2 am.
Enjoy this absurdity right here (transcribed after the clip below, in case you can’t watch/listen right now):
A night at Bub City, 7 missed phone calls at 2 a.m., Theo Epstein making a signing mid-beer.The story of David Ross’ Chicago Cubs negotiation is truly an ALL-TIMER ?? pic.twitter.com/1STnDE1TF1
— Lovable Reunion (@LovableReunion) April 7, 2026Here’s the story, written out:
“We go to Bub City, it’s Theo (Epstein), Jed (Hoyer), me, my family, my agents. We’re sitting there talking, I’m like, ‘Y’all got a backup catcher?’ And they go, ‘No.’ I go, ‘You need to sign Rossy. You need a veteran, veteran dude that knows what his role is.'”
“I mean, I’m bugging the hell out of Theo, and finally he’s like, ‘You get him on the phone, we’ll work a deal out.'”
Lester continued: “I called (David Ross’) phone seven times … no answer.”
Ross chimes in to the story: “I’m waking up, going (looks at phone), “Oh, Jon’s drunk.”
At this point, Lester asked his wife to give him Ross’ wife’s phone number. Ross pushed back at first, again repeating “Jon’s hammered.” But when he realized whose phone number was calling, he says, “Okay, I should probably answer this.”
Lester again: “I’m like, ‘Hey bro, I’m sitting here with Theo, do you want to come to Chicago?'” And he’s like, ‘F*ck yeah, let’s do it!'” I’m like ‘What would it take to get you here?'” ‘He goes two (years) for six (million).'”
“Theo’s standing there, at 2 am, and I go ‘Hey, he wants 2 for 6.’ And Theo starts drinking his beer. And he just goes *holds up hand alternating between 2 and 5 while drinking*
“And he just keeps doing this, over and over, wouldn’t say a word to me.”
“So I go, ‘Uh, Rossy, he’s saying 2 for 5.’ Rossy goes, ‘Okay, see if you can get me five and a half.'”
At this point, after Lester related Ross’ counter, Epstein is still just drinking his beer and repeating the 2 – 5 motion. Lester relays Epstein’s stubbornness to Ross, and Ross just goes, “… Alright, I’ll take it … see if you can get me a suite on the road.”
I am dead. How is THIS how something that ultimately became THAT IMPORTANT happened?
***
Ross did, indeed, sign a two-year, $5M deal with the Cubs ahead of the 2015 season. Ross, of course, went on to have a meh first year in Chicago (2015), though he did help the Cubs reach the NLCS along the way, stewarding a very young and inexperienced team while handling Lester all year and in the playoffs.
Then, he had one final great season in 2016, slashing .229/.338/.446 (101 wRC+) with a double and two homers that postseason, including his big homer in Game 7 of the 2016 World Series. He was later carried off the field on his teammates’ shoulders when the Cubs finally won it all.
And it all happened because of a drunken phone call at 2 am.
The lesson, here, kids? Go out and get drunk with your friends. You might just make $5M and win the World Series.
Hence then, the article about jon lester drunkenly negotiated david ross deal with theo epstein from a bar at 2 am was published today ( ) and is available on Bleacher Nation ( Middle East ) The editorial team at PressBee has edited and verified it, and it may have been modified, fully republished, or quoted. You can read and follow the updates of this news or article from its original source.
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