We knew that there had to be a Rational Explanation:
Dr. Charles Ate Theo's Deal!

Red Sox Hub-The Real Story Behind Theo Epstein's Departure

Actually, there is a rational explanation for why Theo never got around to signing his new contract, and it centers around the dentist and a Halloween party.

P.R. spin doctor Charles Steinberg, a.k.a. "Big Sox Stein", was in charge of delivering the documents for signing on Friday, when apparently a little bit of orange frosting from a Halloween cake "somehow" got onto Theo's new deal...Me-thinks it came from the dentist's third piece. Well, Charles certainly can't pass up Halloween frosting; What started as just a little lick of the contract ended in, before Steinberg knew it, an inhaling of the entire 10 page deal! Dr. Charles, in an effort to cover up his Halloween snack-hap, attempted to reprint the original deal-but he was too late! Theo angrily left the Red Sox offices on Friday, obviously offended at not being offered the new deal by 7 p.m. as promised, and the rest is Red Sox infamy.