Study your machine
The more tempting and desirable the prizes, the lower the chances you'll win. Expect machines with expensive prizes to have claws that move faster, grip looser, and generally do everything possible to foil your attempts to snag their contents. If all you want to do is win something, machines with cheaper prizes are a better bet.
Another good idea? Look for machines that aren't packed tight with prizes -- a little space can go a long way. It's also worth sizing up the pile of goodies. Are they stacked in such a way as to make it hard to pull them apart? If the prize you want is tucked under another toy, it's going to be that much harder to grab, as the claw typically isn't strong enough to dig a toy out from underneath other objects. Perhaps a little strategic repositioning is in order before you tackle the big prize -- or perhaps there's another machine with a more favorable arrangement.
Timing is everything
Don't be afraid to take your time. Depending on the machine, you'll likely have a total of 15 or 30 seconds to hit the all-important "Drop" button. There's no harm in taking almost all of that to make sure your alignment is dead-on. Plan to hit the button when there's about five seconds left on the clock, and you'll have ample time for the machine to haul out whatever you've snagged.
Use a spotter
Having two eyes is overrated. Unless you're some sort of ping-pong prodigy, your depth perception probably ain't all that -- and if you want to boost your chances of snagging that awesome claw-machine prize, you're going to need some way of augmenting it. Some sort of cybernetic implant would be ideal, but if you can't swing that, find yourself an accomplice.
How's that going to help? You look after the side-to-side alignment, and have your partner stand around the corner of the machine and take care of the front-back direction. No matter how lousy your depth perception might be, as long as your spotter is on the ball, you'll drop the claw right on the prize every time.
Watch and wait
But that might not be enough. According to a report on the British show Brainiac, some claw machines are configured so that four times out of five (or nine times out of ten) they'll deliberately grab the toy with a greatly weakened grip. Only on that lucky fifth run will it use enough force to actually keep hold of the prize. In other words, they're rigged.
True? False? Nobody seems to know for sure -- except the manufacturers, and you can bet they're keeping a tight grip on the info. Still, if you're sizing up a busy machine, it may make sense to watch other players and see if there's a pattern to their wins and losses.