Always love talkin' strategy. As a qualifier, I tend to be fairly statistical in my approach to the game, which means that I'm not big into taking low-percentage risks unless it's late in the game and I desperately need something to happen to get a run to tie. All of the offensive plays listed here are fairly high risk plays that are designed to help get you that one run.
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Originally Posted by Rod
Hit & Run
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In a hit and run, you start the runner--usually on first--when the pitch is thrown, and expect the hitter to make contact with the pitch. The idea is that if the hitter gets a single, the runner will already be almost to second base by the time the ball gets through the infield. This gives him a better chance of taking an extra base. In real life, it also forces either the second baseman or the shortstop to break towards the second-base bag, which can open up a hole in the infield. Finally, it also makes it more difficult for the opposing team to turn a double play on a ground ball. Smallball guys love this play.
Two principle dangers to using it. One, in the case of a line drive to the infield, it's very easy for the runner to be doubled up, as they'll have no chance to make it back to first base. Two, if the batter doesn't make contact with the pitch, the runner has a high likelihood of getting thrown out. The reason is that the runner needs to pay attention to where the ball is hit in order to react correctly in the case of a fly ball or line drive out, so he can't run as fast as he would if trying to steal the bag. Therefore, it's best to use this play with good contact hitters (high contact, low strikeouts) when facing pitchers with good control (and ideally low strikeouts), in counts in which it's likely that you'll see a strike (1-0, 2-0, 2-1 for example...NOT 0-2 counts).
Personally, I don't use this play. Too much of a risk of getting caught stealing, and I don't like forcing a hitter to swing at a pitch that could be a terrible pitch to hit. Only time I'll even consider it is if it's late in the game, I need one run to tie, and I have a good contact hitter facing a good control pitcher.
This is much the same as a hit & run, except that the hitter is only expected to swing if he sees a pitch that he likes. The runner still has to be aware of what's going on, so the steal is maybe a little less likely than in a straight-steal situation, but at least the hitter isn't forced to swing before the pitch is even thrown. I like this one a little bit better than the hit & run, but only marginally. It should only be used when you have a good runner on the bases, though, because otherwise they're definitely going to get thrown out.
One place where I will use this play is to send a fast runner on a 3-2 count. This way, if the hitter takes the pitch, it's most likely going to be a ball and the runner will automatically advance to second anyway. Does still occasionally result in a strike 'em out, throw 'em out double play though (but so does the hit and run).
This is only is possible if you have a guy on third base and less than two outs. The hitter tries to bunt the ball, while runner breaks from third as the pitch is thrown and tries to get to the plate before the defense can get the bunt back to the catcher. It's risky because you have to send the runner as the pitch is thrown, which means that (again) you have to be confident that a) the hitter will get a pitch somewhere in the vicinity of the strike zone (control pitcher, with a count likely to result in a strike), and b) that the hitter can make contact with the ball and *not* pop up the bunt (good sac bunting skills). Finally, because you're effectively just giving the runner a little more time to steal home here, it's important that the runner be extremely fast.
This is again a play that I would only use in late innings when I desperately need a single run to tie, and have the right runner on third and bunter at the plate. Otherwise, I'd much rather let my hitter take a swing and hope for either a hit or a sac-fly.
In real life, it may have it's best value as a "shock" play. If the defense isn't expecting it, you can score an easy run. But I'm not sure that the "shock" factor translates over into OOTP all that well.
This is becoming pretty popular these days among big-time pull hitters like David Ortiz, Ken Griffey Jr., and Adam Dunn. What essentially happens is that the infield defense "shifts" such that three infielders will be on the side of the infield that the batter usually hits to. So for those guys, all left-handed hitters, the shortstop plays behind second base, the second baseman plays between his normal position and first base, and the first baseman plays a little closer to the line than normal. The result is that it's much harder to get a ball through the right side of the infield than normal.
The downside is that the other side of the infield only has one fielder, which means it's pretty easy to get a hit that way. Therefore, you should only use this play when a hitter has a strong tendency to pull the ball (check for "pull hitter" in the hitter description). I actually like this play under certain conditions--when used with the right hitter, it can really help your cause. Adam Dunn, for example, plays for my Reds, and almost never hits a ground ball to the opposite field. This makes the shift a particularly effective strategy against him--and he's expressed frustration this season because so many teams do just that.

It's also best to use when your pitcher is throwing on the inside part of the plate, as those pitches are more likely to be pulled (not that you have much control over that in OOTP). But you have to be careful, because if the hitter *can* hit a ground ball to the opposite field, he's much more likely to get a hit.
Hope that helps!
-jinaz