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It just dawned on me that I should read the manual and see how if I was missing something on the stealing. Indeed I was as apparently you can't do this under "baserunner" mode(by pressing B) it must be done in "batter" mode.
I did this twice on two accounts: "phuture 909" and my wife's "lilmo13". As you can see, i was able to get Thief and Organized Crime on the same game for the lilmo13 account.
Most of us already have a super good team and a super bad team roster, if you haven't then do it(if you need help, then look in the forum)
While on "batter/batting" mode you can have your baserunner steal bases by using the LEFT STICK(LS) and the X button. Up on the LS + X = steal second
Left on LS + X = Steal third
Down on LS + X = Steal home
Have the LS in the direction wished. Watch for the pitcher start moving and immediatly press X. With your super team/bad team match up you are pretty much guaranteed a 100% success rate. I did it twice without getting caught. If you do, i would sugguest restarting the match.
Keep stealing away your second and third bases. Once on Third, just get a hit to get on first base. Rinse & repeat.
Here is my specifics in case anyone wants to know:
downloaded stadium patch
accepted updated from live
difficulty: pro
other misc settings: default
cheats are ok - did it with super bunts ON, then all cheats OFF again used the following "situation" game mode: runners on base "1st base", the rest was default, super team as Away, bad team as Home. The runner on 1st base is to give you an head start on getting on base, i'm sure if you set it 1st & 2nd and do a double steal it'll still work.
The achievement pops during the game, on the 6th steal.
If you have any questions, let me know so i can clarify.
I'm quite certain this will be the proper stealing command for all steal related achievements: robbery, thief(proven), organized crime (proven on my end), double steal, burglar,