What's often confused is whether a player must measure using the club with which they'd be playing their next stroke. The answer is yes in one case, and no in the other.
Determining if You Get Relief from an Obstruction
Rule 24 covers Obstructions, both movable and immovable. If your ball comes to rest near an immovable obstruction, you are entitled to free relief if your ball "lies in or on the obstruction, or when the obstruction interferes with the player's stance or the area of his intended swing." (We're talking through the green here; for other parameters, see Rule 24.)
Your ball is near the obstruction - the question is, does the obstruction interfere with the path of your intended swing? If so, you should identify the nearest point of relief, then drop within one club-length of that point, not nearer the hole.
To determine if the obstruction interferes with your intended swing, you'll need to simulate that swing. Here's the key point in this FAQ: When simulating the swing, you should use the club you would use if the obstruction was not there.
If you are 100 yards from the green, and you'd normally hit sand wedge from 100 yards, then you must use a sand wedge. Simulate your stance and your swing; if, using the sand wedge, the obstruction interferes, then you get relief. If it doesn't, then you don't. You can't pull out a 3-iron or driver - or any longer club that you would never really use from that distance - just to ensure that the obstruction will, in fact, interefere.
In the Rules, this procedure is spelled out in a note to the definition of "nearest point of relief":
"In order to determine the nearest point of relief accurately, the player should use the club with which he would have made his next stroke if the condition were not there to simulate the address position, direction of play and swing for such a stroke."
So when determining whether you are entitled to relief you should use the club with which you'd play the stroke if the obstruction did not exist.
Measuring One or Two Club-Lengths
When taking relief from an obstruction, the player is allowed to drop within one club length of the nearest point of relief. Throughout the Rules of Golf, there are many situations in which a player will need to measure one or two club-lengths from a particular spot.
Let's follow up with our example from above involving the sand wedge. Using your sand wedge, you've determined that you are entitled to relief and you've found the nearest point of relief (that point where the obstruction doesn't interfere with your swing when using the sand wedge). Now, you must drop within one club length of that nearest point of relief. Do you have to use the sand wedge to measure one club length?
No, in measuring club lengths for a drop you can use any club you want. That means most of us will use the driver, the longest club in our bags; some golfers might carry long putters that are longer than drivers, and if you are one of those golfers, you may use the long putter. You can use any club in your bag to measure club-lengths for taking a drop.
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