All one need do is read a few profiles of Chiofaro to understand that he is pugnacious, tenacious, stubborn, boisterous, and maybe someone only his family truly loves. Those aren't necessarily bad attributes, but for the moment, it has left him as a one-shot wonder as a developer: International Place. In short, his list of adversaries is now a lot longer than his list of friends.
He got tossed as manager of his International Place by the union pension fund that was majority owner; he had a nasty legal fight with Tishman Speyer (whom he publicly called a "band of pirates"); he got kicked off two projects because he couldn't sign a lead tenant (one was One Lincoln, in which he subsequently sued Hynes and Gale and lost; the other, in 2000, was a city-owned waterfront parcel that he did nothing on for two years after being given development rights); he filed for bankruptcy on International Place, and nearly filed for bankruptcy on the same property a decade earlier.
Chiofaro's problems and difficulties pre-date Menino, and while Menino may not be the sharpest knife in the drawer, he knows politically that opposing Chiofaro helps Menino, if only because Chiofaro has so many foes.
Chiofaro loves a fight, but picking fights doesn't mean you come out a winner. Chiofaro knows that, for better or worse, in Boston, you have to kiss the ring of the mayor and get his blessing if you want to proceed. The President of Harvard goes and kisses the ring, and Harvard gets pretty much what it wants in Allston, and the residents of Allston pretty much get rolled over.
Menino knows there are a lot more votes in the Harbor Towers and the North End opposed to Chiofaro and his tower then there are in favor of it. Voters in the rest of the city don't really give a rat's ass. The far easier course is for Menino to oppose this project. But Chiofaro has done just about everything he can do to publicly portray the mayor as a stubborn, insipid fool. And if Menino, who, IMO, is ultimately an insecure individual, concludes you are ridiculing him, you aren't going to do business with him.
And Menino knows a lot about Chiofaro's finances. He figures if need be, he can outlast Chiofaro and the $85 million balloon payment on the loan that helped Chiofaro buy the garage. And if Chiofaro can't refinance, the garage gets put up for auction by the noteholder. Chiofaro's ability to refinance is helped immeasurably be either getting construction of a tower started before then, or in getting a building of a certain size permitted.