Fooch's note: This story starts at around exactly 27:00, and runs to the 38 minute mark. I've embedded the audio below. I think the whole story is worth a listen, but I'll give you the short version. Some of you may recall Tim Kawakami tweeting about how he had a bet with Jed York regarding the new stadium. York said it would be done for the 2014 season, Kawakami thought it would not be done until 2015. They initially were going to bet lunch on it. It turned into dinner at French Laundry (viewed as arguably the best restaurant in America, and you definitely pay for it). Kawakami goes into some back story about what happened at the restaurant. According to TK, Jed asked if he could bring along his wife but said he'll pay for her. TK was fine with that.
It ended up being Jed, his wife, TK, Matt Barrows and Ann Killion. The latter two paid for themselves, and TK was going to be on the hook for himself and Jed. On the night of the dinner, when the bill came, Jed didn't make a move to cover for his wife's bill, leaving TK to pay for all three. It was approximately $600 per person with the small tip. TK ended up paying $2,100 in covering Jed and his wife.
He says he has heard the 49ers blame that incident for why TK crushes them. TK basically says it's because they do stupid stuff, but he also thinks that incident sort of helps explain a little bit of the 49ers under the York family. Believe what you want from it, but it's an intriguing listen to hear the whole story. What was kind of interesting was that TK didn't think Jed was necessarily just trying to stick it to him. He thinks Jed was just oblivious to the nature of the amount of money involved. I don't really know which to believe, but given that he promised to pay for his wife, it would be kind of douchey to go back on that given the price of the meal.
I know he isn't the most popular writer on here, but at around 27mins in this podcast TK has a fascinating story explaining his relationship with Jed York, and how it kind of went downhill. Its a good insight on the kind of guy who runs this organization. I won't tell any more details, you're better off listening yourself.