New Driver or New Putter?
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The right putter can make a huge difference. Funny thing though, I'm not at all sure that the cost and "rightness" are nearly as tightly associated as they are with a lot of things in life. With a putter it is about how it looks to you as you align, how the weight feels as you swing it, and how it feels when you contact the ball. That last is real hard to put your finger on, but is the reason there are so many different face inserts and ways that the face is milled. What feels good obviously differs from person to person.
Go find as many putters as you can to fool with and take the time to really try 'em all out. Give the ones that look "funny" to you a go too. There are some goofy looking ones out there, but if putts start dropping... well, maybe it doesn't look so bad.
Drivers are pretty important too, but only you know how badly you need a new one. If you can't keep it out of the woods I'd say you need a replacement worse than I would if you simply hope for an extra 15 yards.
I don't know what your set makeup is, nor where you struggle, but another club you might want to consider is a nice sand/lob wedge (in the 56-60 degree range, I like 58*). Buying one would give you incentive to practice those close to the green shots, and between that and better putting you'll almost certainly shave strokes from your score cards.
I planned to spend about $250 or so if I were to get a driver. While I get the point that you use the putter on every hole, I guess I've never even messed around with other putters at the store and never thought it would be worth spending much money on club used to tap the ball 10 feet or so. I'll take the advice and go seriously check out putters and really try to see/feel the difference. Putters are something I know very little about, and honestly didn't even know you could get "fitted" for a putter so I'll check that out.
This is a great question.
I have been golfing for over 50 years, and during that time I have collected 20 putters that I still have in my basement. I have have new putters and old putters. I have long putters, short putters, and medium length putters. I have blade putters, mallet putters and 2-ball putters. I have center shafted putters, and putters with an offset hosel. I have putters with normal grips and ones with jumbo grips. From my point of view, I enjoy playing a putter for 2 or 3 rounds and then evaluating its efficiency. If it gets a good grade I keep it in the bag for a while longer. When the putter inevitably has an off day, I go to my basement and replace it with another one. This summer I have used 5 different putters at one time or another: Ping B60, Ping Piper H, Ping Anser 2, Odyssey White Steel 2-Ball, and the Odyssey White Hot XG #9. Right now I am using the 2-ball putter, but most of the summer I used the B60. Personally, I enjoy using different putters, but I also understand the value of finding one putter that works, and staying with it - just like an old friend.
My journey to find a driver that works has also been an exciting one. Over the years I have played different models of TaylorMade, Ben Hogan, Wilson, Ping, Mizuno, Titleist, Adams, Callaway, and Nike drivers. I have played lofts from 8° - 13°, graphite and steel shafts, stiff and regular flexes, lengths of shafts from 44" to 46", and midsize and regular grips, Currently, I have 6 drivers in the basement, but am only actually using three: TaylorMade R11, 10.5° loft, regular flex; TaylorMade RocketBallz - 9.5° loft, stiff shaft; and, Ping G5 Driver, 9° loft, regular flex, Grafalloy Blue shaft. I have to admit that I won the R11 online and the Rocketballz at last spring's Golf Show, so I didn't have to shell out the big $$$ for these clubs. The G5 was an eBay purchase.
Now, getting back to your original question, " New Driver or New Putter?"
If you have $250 to spend, my advice would be to buy a putter and a driver. (No surprise considering my background.) Instead of buying a brand new driver, I recommend that you go to eBay and purchase a model that is a year old. For drivers, you can easily get a TaylorMade or Callway driver with the loft and flex that you want for $150 or less, and then get a Ping or Odyssey putter for less than $100.
Best wishes on the adventure of upgrading your golf clubs.
I would buy the club that could help me the most.Take a look at how your driver is treating you and then your putter. Which one is the weakest link in your arsenal? To me the putter is the most important club in the bag since it is the most used club for most everyone. The driver you only hit probably 12-14 times a round or less. The putter more than likely 30 or more times a round. If you are hitting fairways but having too many putts get a new putter, but get fitted for it.
So long at you tap the ball 10 feet or so and it drops into the hole most every time I wouldn't recommend spending any money on a new putter! It's the dropping into the hole that's the rub.
There is a thread, I think in the Golf Talk sub forum, on how people got to be single digit handicappers. It was active pretty recently, so shouldn't be hard to find. Page after page of the same thing; "get your short game together." Good pitching/chipping and putting will take more strokes of most golfer's score cards than great drives.