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heh sounds like the atlanta braves to me.
The key to taking over a terrible team is to try to get rid of over paid players like you said, and to hire the best possible coaching staffs you can after losing terribly your first season and getting the number one pick of course
Second big thing is to have a multi-year plan. The first season, either pick a second baseman or shortstop, or the number one SP and build your farm around that guy
For the second season (assuming your draft is in june) your team is still going to be pretty terrible, so just suck it up until that season is over as well, and hopefully you have the number one pick once again. for your first pick this second season, pick the other MI that you didnt pick the first year. (E.G. if you picked a SS the first year get the 2B the next.) or if you went with SP the first year, go with SP again the second.
hopefully, by this time some of the more over paid veterans either had their contracts run out, retired or were "sold" by you by the end of the second season. (hopefully your able to trade them away to a team like the NYY for a prospect and extra cash)
for the third season, try not to place below 5th in the league (your job may be at stake) but make sure your get a high pick again. for your first pick you have even more options available depending on who your building your farm around. hopefully your first draft picks have developed enough for them to be at the majors or close to it by now.
The fourth year your first draftees SHOULD be major league ready, and you can finally trade off some possible prospects for more veteran talent who are not quite in their prime...ball players around 25 or 26. the key here is to have NOONE above 30 if at all possible.
and by the fifth year you should be making a run at the playoffs.
your sixth year should be IN the playoffs, perhaps in the world series.
(tons of tiny little details in between to tweak your team, such as better coaching staffs and slowly siphoning off anyone over 30 that way all your players are relatively the same age and should keep your problems of key players dropping talent at critical moments to a minimum.)
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