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Tony says Tom drinks tea and orders Domino’s. Tom says thirty years of reading markets means he can read a quality sandwich just as fast. Tony is Brooklyn-born Italian, raised on Sunday gravy, prosciutto, and bread with an actual soul — and he’ll remind you of that every chance he gets. He’s also been known to brag on X about how often he beats Tom in a bet. Which makes it even more embarrassing that Tom beat him in a blind coffee and tea taste test, and now this. Tony wants his dignity back, and he picked the one battlefield where heritage is supposed to matter: Italian subs. These two have been close friends for decades — same city, same subs, and apparently the same need to settle things with a $20 bet and zero mercy. Four Chicago delis ranked by The Infatuation. No labels, no menus, no hints. This rematch is exactly as chaotic as you’d expect from two guys who’ve known each other way too long. Decades in, and they still show up for each other — even if showing up means taking your $20.
#lossdog #chicagofood #italiansub #foodchallenge #blindtastetest #tomsosnoff
Tom Sosnoff built thinkorswim by trusting pattern recognition over conventional wisdom — and that same instinct is what makes him a surprisingly dangerous opponent across any blind taste format, coffee or Italian cold cuts alike. Tony’s argument is essentially that taste memory is inherited, not learned — that decades of Sunday gravy is worth more than decades of reading markets. What makes this more than just a food video is the friendship underneath it: two guys who’ve spent the better part of their careers in each other’s orbit, still showing up to argue about sandwiches like nothing’s changed — and if you watch closely, even the trash talk has a way of making the other guy look good. Chicago’s Italian sub scene is genuinely contested — Paulina Market, Fontanos, Bari, and Damato’s each have fierce loyalists and completely different identities — and stripping away the labels reveals how much of taste is memory and how much is actually the sandwich.
16 Comments
I felt bad that Tony is always on the losing end of our battles. So, I had to throw him a bone. Tony may not know much, but he sure knows his meat. Let us know your thoughts. Tony and I will both reply to your comments. AND, don't forget to join me on my next venture at lossdog.com. Sign up today–there are some meaty rewards in it for you! –Tom Sosnoff
At the end of the previous video when you said you might battle over gabagool I thought you were kidding.
The way Tom had that crazy clean sweep in the previous battle, Tony needed that overtime win in Liars Poker. 1-1
They miss each other lol 😂
The Bat somewhat redeems himself or did he? Since these were Italian subs I may have to rethink my comment.
These guys are great. Never leave your friends (friend’s) behind. It’s all about the punctuation.
Very well done!
Amazing
Dude, don't knock Dominoes, it's a great company, stock and the pizza is good too
Loved it! 😂😂 Scott catching strays, fancyboy 😂😂🍷
This episode needs a plaque on the wall!!!
Are you saying Tony's palate is 'public'? Pasta challenge next guys! Can't wait for the T vs T app: "The traders guide of fine dining in Chi-town". Now let's make some markets on the next episode(I may even sell puts on Tony's choices)!!!
It's just good to see Tom smiling again and sadly it's always at Tony's expense. 😂 It's great to them laughing together. Let's Scott know it's ok to laugh too. You're all good guys did well enjoy it.
😁🎉
Great duel✅️💯😄.
last time was drinks. now its food!