The shortstop position is one of the most important positions on the field. Many balls are hit in the direction of the shortstop and that player is normally the best defensive player on the field. He must have good range, a good glove, and a strong arm. This combination of skills and athletic ability are a tough combination to achieve. For a shortstop to continue playing that position a he gets older, he must possess a desire to continually improve his fielding and his arm. This section focuses on some plays specific to playing shortstop.
Where you position yourself will depend on a number of factors. The basic shortstop position is one in which you are close enough to field an average ground ball to your left and right and still have time to throw out an above average runner at first. Arm strength is the primary consideration for determining depth. From there you will need to adjust your position depending on the speed of the hitter and whether or not you will need to cover second (double play; steal attempt). If a faster player comes up to bat, move in to compensate. It does no good to field a ground ball if you can't throw the runner out.
Don't position yourself so deep that you have to make a perfect play in order to get an out. Sometimes a clean transfer of the ball from your glove to your throwing hand doesn't happen. You don't want that to cost you an out. A good way to check yourself is to track how close the play is at first base. If you are barely throwing out a runner on a routine ground ball, you are probably playing to deep.
Normally the second baseman will cover second on a steal attempt with a right-handed batter at the plate and the shortstop will cover second when a left-handed batter is up. Try to position yourself so you can still cover your area, but not so far away from second that you have to sprint to second to get there ahead of the runner. Once they see a runner stealing, I teach my players to shuffle towards second until the ball has crossed the plate, then to run hard to cover the base. By shuffling the first couple of steps they are still squared up to home and can stop and go quickly to their right if the ball is hit that way. This is something that really needs to be practiced with the catchers throwing down in order for your players to get a good feel for the timing required.
When you are starting a double play, you want to get the ball to the second baseman quickly and accurately. You should be aiming to put the ball on his glove hand side at chest level. This will allow the second baseman to start his momentum moving toward first as the ball is coming. Make sure you don't try to lead him off the base, your throw should be in line with the inside of the bag.
Quickly delivering the ball to second shouldn't be mistaken with rushing. You want to make sure you get that out at second. We've seen, at all levels, the fielder that makes a fielding error or a throwing error because he was in such a rush to get the ball to the second baseman. Make sure you field the ball first, then throw. The image above shows a throw being made from the shortstop. This throw is being made from the "shirt sleeve". This is a short throwing motion that allows the player to quickly deliver the ball a short distance.
On any ball hit directly at you or to your right that you can get in front of, catch the ball as you normally would and instead of moving your feet and body like you do when you're throwing to first, you will want to throw from the fielding position. As you bring the ball up, step slightly toward second with your left foot and use a small arm motion to deliver the ball to second.
On a ball hit to your right that you have to field backhand, you will want to plant your right leg after you make the catch and make a strong accurate throw to second. You may be tempted to jump and throw in one motion after catching the ball, but for most players the arm strength and accuracy aren't there to make this play. It will be quicker and you'll have a better chance if you plant and make a good hard throw to second.
On a ball hit to your left that you can get in front of, you will want to deliver the ball underhanded to the second baseman. As you field the ball out in front of you, turn your hips and clear as quickly as you can your glove hand to the left of your body. This will allow the second baseman to clearly see the ball as it's being delivered. As you underhand the ball step with your right foot in the direction of second base. This will help you follow through as you deliver the ball.
Sometimes you will field the ball behind second and won't be able to get in front of it. Fielding the ball off your left side will put you in a position that makes it difficult to underhand the ball. In this case you will need to make a backhand toss to the second baseman. This is a difficult skill and must be practiced over and over again to become good at. With the backhand toss you will turn your thumb towards the ground and with your elbow, toss the ball across your body.