This is a really interesting thread that some people seem to be trying to force into something that it's not even though it seems quite clearly hypothetical, would you go back in time and trade prospect X if you knew it would win the Sox a World Series. My gut reaction was "of course" until someone posted about Ted Williams, and then I realised it's not at all cut and dried. There is value in getting to see an all time legend play over a long períod of time and I'm not sure it's as easy as it seems to reflexively say "we play to win". If we'd not won in 2004, I am not sure I would so easily be able to dismiss seeing Pedro for example with a "OK you can go back in time and not get Pedro and instead you DO win in 2004". Watching Pedro pitch for several years feels as YOUR guy feels like an incredibly valuable and perhaps too easily taken for granted boon.
I had to experience this in person when I made my first trip to Fenway Park in 2004, I was a crazy big fan of Nomar, the way he played, the way he had his plate routine, I loved that guy, yet imagine how crushed I was that literally weeks before I arrived, he'd gone, and in a cloud of controversy that still feels like was never really explained fully. Of course, 2004 would have a wonderful ending, but those of you who get to go every week probably can't understand how crushed, crushed I was that months of excitement at coming to see the Red Sox FoR REAL would NOT include seeing Nomar at the plate. It became even more annoying when the trade was justified forever as "we would never have won the World Series had we not made the trade". Really? Because the history I experienced only had the trade happening, I missed the bus to the alternate universe where the trade didnt happen so I dont know what happened there. It still kind of bugs me that this is just bandied about like a proven fact. We don't know the team wouldn't have won the series had Nomar stayed, at least IMO, no matter how well OCab and eyechart contributed. Well, because 2004 was 2004 and it followed 1918 I can hardly say "yeah I'd go back and keep Nomar" for my own selfish reasons, and I'd only really been a part time Sox fan since 1986 so wasn't feeling the 86 years like you guys, but still, I can understand the appeal of following a group of players you identify with and enjoy watching, regardless of bottom line success.
As an extension of the question, I often wonder about the more realistic version of this being how bad do you accept the Sox being if you know it will keep them mounting a challenge every 2 or 3 years pretty much throughout your life, compared to trying to get the "perfect roster" every season and using every dollar, every trade prospect. Indeed, how much value do you guys assign to a "home brewed" team in general, surely easier to stomach now given recent successes. For me, in theory at least, the appeal is high, keep the young uns, throw them in, accept some struggles and get to see some of them become lifelong achievers as Red Sox. Of course, it's rare that most of them pan out in reality.