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The rule that proves the exception
We'd all like to think when we win it was our being better GM's than our competition and when we lose it was bad luck.
Some strong teams got that way through lots of hard research by the owners.
Some got that way because they guessed right (got lucky) on a few great players.
Some made some trades with newbies that perhaps slipped by the Commish.
Some teams had great formation drafts.
No matter how you got a strong team, once you have it I think it is fairly easy to keep it strong. Even if you turn it over by trading...if you trade A-Rod you are likely going to get pretty good talent in return.
It is pretty hard to start with a bunch of INN guys and trade for talent. To build from near nothing through the draft takes years even if you guess right. Look at this year's rookie draft. Do you really know who is going to be the best 10 players in that draft 3 years from now? Give me a list and we'll check it in 3 years. TRAD or RT though RT is tougher IMOP. [with your successful record, you'll probably do great and I'll eat crow. I drafted Ankiel & Greinke #1. Why do I get the head cases?].
The game rules make it even harder. You have to cut to 27. If you have solid stars, you know when you cut you still have a pretty good team. If you are building, you aren't so sure which young players to keep and which to cut (Gomes for example last year??). With a solid core, you can afford those mistakes and you can also draft youth and wait 2-3 years (I had Vernon Wells on my DNP list for 2 years). Young pitching is especially hard to predict while if you have a solid core of reliable starters you can gamble on some potential young stars.
I'm not in favor of tanking or rules that encourage it. Ken's ideas do make sense, but what I would prefer to see are rules that give new managers favoritism no matter how good or bad their team. If a new manager starts out successful, they are likely to stay with the game. If they start out losing over 100 games, they are likely to drop out before the season ends. Give them a headstart for 2 years (no cuts till after the FA draft and then cut to 35 for example. A free FA round after the FA draft is completed but 2 months into the major league season when they can see who would be a good future pick up). Then the 3rd year drop them to the same rules as the rest of us.
Get 'em hooked good, then reel 'em in.