***I was thinking about the "win now" idea vs playing for the future. People usually talk about winning now when it's a veteran team like the 1987 Tigers. Yes, trade a prospect like Smoltz for Doyle Alexander who can help you win now...because the team is aging and you need to take advantage while you still can.
But it's an odd concept to have a young team and think, let's postpone the winning for later. If your young team has gotten better earlier than expected, I think you should definitely try to maximize it. It's not just that prospects don't always pan out as Peter says above...or they take longer than you think (hello Colt Keith!) but the elephant in the room is - *no team wins very often!*
There hasn't been a repeat World Series winner in 25 years.
The Los Angeles Dodgers have been in 4 World Series the last 7 years and have managed to win twice but one was the shortened pandemic season of 2020. It barely counts :-). The other was last year of course which was hugely helped by signing the best player in the world to a massive contract. They are not really an example of building a young homegrown team.
The Yankees have made the postseason 15 years in a row but haven't won a single World Series in that time. They've been in 4.
Besides the Dodgers, we've had some non-consecutive repeat winners in the last 20 years like San Fran, St Louis, Houston & Boston but virtually all were 4 or 5 years apart.
And we've had just as many teams win once and then have little playoff success after that.
Kansas City won in 2015 and haven't been in the ALCS since.
The Cubs won the following year and haven't really come close to getting back. They beat Cleveland who also haven't been back.
The Nationals won in 2019 and haven't even made the playoffs since.
Texas won in 2023 and have now missed the playoffs 2 years in a row.
So I think the answer is....always try to win now! That doesn't mean make stupid trades of course but playing it cautious is unlikely to generate huge rewards. And endlessly building a young team that will be consistently competitive year after year might work but competitive isn't the same as actually winning.