Do we try to win now, or do we try to win later?
It's the eternal question for a baseball team. Do you spend money in the years directly infront of you attempting to maximize your potential of winning it all right now, or do you defray costs in order to maximize your potential of having a consistent playoff team later.
For various reasons I'm usually a win-now guy. The idea that you have to choose is founded in the "money bucket" theory that you guys know I hate. Also the future in sports, even 3 years down the road, is too variable to plan on. But let's try to take a more mathematical approach.
Let's say you make the playoffs and you have a 50% chance of winning any series. That's really rough but also pretty fair. Your chances of winning it all in this purely mathematical scenario would be only 12.5%. If you made the playoffs with these odds you wouldn't expect to win a World Series until you made the playoffs 6 times.
How does that work? Well if you have a 12.5% chance of winning, you have an 87.5% chance of not winning. Your chances of not winning in back to back years is 87.5% * 87.5% or 76.5%. This continues on and on and your chances of not winning 5 years in a row is still above 50%. (51.3% to be precise). So, if you made the playoffs 5 years in a row and had a 50% chance of winning every series, you'd STILL be more likely not to have won a WS than to have won it. Just barely but it's so. In the 6th year it flips.
OK so what if you go all in? How does that effect things? Well depends on how much an advantage you think it gives. Some people jump right away and say something like... 75% chance of winning a series. That's ludicrous. The best teams ever playing a mix of playoff teams and terrible teams don't hit a 75% winning percentage. 75% is way too high. Let's look at it another way. The Nats won 59.3% of their games playing a mix of teams. How many games would they win playing ONLY playoff teams? Hopefully you can see that even 55% is generous. (in fact the Nats played 46% ball versus playoff teams this year, but 56% versus NL playoff teams if you want to parse further)
Let's go with that for now though. What changes if the Nats have a 55% chance of winning every series? Their chances of winning skyrocket all the way to... 16.6%, which makes their chances of not winning 83.4%. Not a big change right? BUT there is a big difference if you look over the course of years. Instead of hitting the "should have won" point in that 6th year, you now hit it in the 4th year. By that 4th year your chances of having won at least one world series are 10 percentage points better. ~52% rather than ~42%
And we're comparing it to an even-steven team. If the "All-in" Nats need 4 years to win, what would the "just get in" Nats need? Well if all-in wins at 55% than just in would win around 45% right (once again forgive the roughness)? They are the worst in the playoffs. Run the numbers... carry the one... these Nats would need 8 years to get to that same "should have won one" point and in comparison to the all-in Nats in year 4 have a chance to have won at least one World Series that's 20 percentage points lower.
So going all-in as opposed to just sneaking in makes a big difference. It may not seem so initially but those little percentage differences add up. Of course there are two big issues here, or maybe three, or even four, now that I think about it. The first is the 55/45 split is probably too generous. 53/47 is probably more in line. That decreases that year 4 difference to 12 percentage points from 20. Still big but almost cut in half. The second is the window sizes we're talking about. Is an "all-in" window of 4 years viable? A "just make it in" window of 6+? Probably not. When we're talking "all-in" we're usually talking about a year or two, versus 3-5 years if you try to just be good enough. Based on the numbers and the 53/47 split you'd (juuuuuuuuuuust barely) rather have 3 years of "good enough" over two years of "all-in". Even if that's a wash, 4 years of making it with what are considered bad playoff odds beats 2 years of making it with good ones.
So it seems like "good enough", when applied to the reality (well somewhat - this is all still just literally numbers on a spreadsheet), makes the most sense. But then you remember - I'm not factoring in the WC. The "all-in" team should avoid that. The "good enough" team would possibly have to face that at least once, probably a couple times. Toss that in twice in four years and "all-in" for 2 takes the juuuuuuuuuust barely lead. Plus I haven't factored in the chances of winning MORE than one.
But it all leads to a single question really - what matters to you. Going all in for a couple of years will very likely slightly increase your chances of winning a title. But it's slightly. We're still saying your chances of NOT winning one are close to 70-75% instead of 80+%. Is that enough of an improvement to you if your team is knowingly going to fall out of contention afterwards?
For a team about to tumble into the void regardless it makes sense to go all-in. For a team that holds out hope of another window opening soon the question is valid just from a competition standpoint. The all-in advantage for winning one series is limited and decreases over time. Business wise "all-in" is not really a sensible idea. The money you'd save by not doing it and presumably make from more playoff appearances and regular season wins probably offsets the small increase in chance that you win it all. You can see why teams avoid the all-in more often than not.
There isn't a big enough difference here to say one way is obviously superior to another. There is an argument for either side based on what you'd expect to see on the field. All-in or not all-in doesn't have a factual answer, it has your opinion. Me? I'm all-in.