To be fair, there is a grass-is-always-greener syndrome here. Marlins fans would likely trade 1 of their rings for 10 years of division titles and competing in the playoffs every year.
Yep, plus willingness to trade based on history shouldn't influence preferences going forward. You have to assume that getting in the playoffs = very solid shot at WS. If you want to win a ring, you'd rather have a solid shot every year than a solid shot 1 year. Too much can happen in a single year (injuries, hot/cold players, etc.) to say that a 100+ win team will be more likely to win the WS than a 90 win playoff team. (Kinda the %age view someone presented earlier, except I'd say the %age when you try to predict this far in advance has to be relatively equal for any year you get in the playoffs.)
i think it sort of depends on the circumstances. 1 1998 team probably has a better chance than 3 1997 teams. And I think RJ upped the 1998 chances a lot because it gave them something they didn't otherwise have (a legit ace) and took them from being a random playoff team to arguably the best team in baseball. On the flipside, adding an ace to the 1990's Atlanta Braves has more of a marginal effect.
Outstanding. Individual players have gotten a lot of shine but a nice, in-depth overview of the entire team from a reputable source is something that I felt had been lacking. Or maybe I just appreciate more positive non-Yankees/RedSox/Cubs/Giants coverage.
Agree that circumstances can change things. But that works for you and the other side--such as another player (e.g. Hitchcock) or team getting insanely hot out of nowhere. Which is why, when predicting going forward, I think you have to optimize for just getting to the playoffs as much as possible. So I'd say make the deals that give you a lot more upside, but not at the expense of very likely killing your playoff chances in 5 years based on expenses + no minor leaguers. Tanking again shouldn't be in the plans, though it may eventually happen.
I don't like the comparisons to last year's Cubs. Didn't they need 7 games to beat an injury depleted Indians team after being down 3-1 while also needing one of the most bizarre timed rain delays you will ever see? As good as they were last year, they got pretty lucky last year. I hope the Astros don't put themselves in a position where "You don't have to go all in. Let's cross our fingers and see what happens". I do understand to not go all-in, though.