It's interesting that the majority view here seems to be pro-Olympics, as that's the opposite of what I'm seeing around me. I'm not seeing "no, we can't do that in Boston", what I'm seeing is "Why would we want to do that here" and "Why should I believe this is going to benefit me?" Promises of magical federal transit dollars only go so far.
Although I know some people who were dead-set anti from day one, I've also heard tons of people start off with "I'd be for it if ____" and then they talk themselves out of it with some combination of (not in order):
- we've dug a huge hole for ourselves on so many governance fronts, we've just got too many priorities in front of anything like an Olympics
- disbelief that if we can't turn around the T for our own sake (lots of evidence for that), we'll somehow fix it for some athletes who'll be spending a few weeks here.
- disbelief in those "magical federal transit dollars" you mention
- Big Dig hangover, terrible MA track record with budgeting a mega-project, however much anyone likes the end result
- DEEP distrust of the IOC and USOC, spilling over to DEEP distrust on the promises that the taxpayers won't take a hit
- DEEP despair on the political dysfunction on Beacon Hill
- the rollout was, as Ruairi put it, done mostly by a bunch of old well-connected guys in suits. To be fair, they had a few others there, too, some young athletes, but the roster is just way too stacked with the usual suspects.
- the USOC's mandate to keep details secret before January 2015 (this was true for the other three cities, too, not just Boston) was seriously bone-headed. I admit to using 20-20 hindsight. The main competition in any given democratic city is not with other cities, it's with the bidder's own NIMBYs. Just be open from day one, let the other cities look over each others' shoulders, so what if they steal ideas. Springing things on people always elicits suspicion.
To all that - some of which I agree with, some not - I'll add my own thought that has grown over time: even if they had ignored the USOC's guidance and been very public through 2014, it would still have been a radically over-compressed time frame prior to the IOC vote in 2017. If Boston really wants to take a shot at an Olympics, we should be thinking about 2028 at the earliest. 2032 or 2036 might make more sense. And we should be expecting to have at least one failed bid along the way - very few cities get in on the first try.
And if we were trying for a bid on THAT time frame, we'd be able to be more sincere about fitting the bid into the larger planning conversation, rather than doing this behind-the-back dribble of "this bid will force us to have the conversation we've been avoiding, AND act on it, otherwise we'll stay dysfunctional forever!"