3 great caddies: Jerry Franklin at Pebble Beach. He swapped out our bags for his two Ping single strap bags (after asking us if that was okay); he regaled us with stories and anecdotes about the courses we played on the Peninsula; he kept our clubs overnight, and showed up the next day on time for our tee times; and, he guided us around the courses as if his life depended upon it -- those greens at Pebble and Spyglass were complete mysteries to me, but after 3 holes in theopening round, I just hit them in the direction Jerry gave us.
Rush at Pinehurst #2 (about 20 years ago). 63 years old, couldn't carry our bags so we swapped out two ultra ultra light carry bags. 2nd green Rush was standing 90 degrees and 45 feet away from me. I've read the putt to break a cup or two from right to left. Rush says "two balls to the right." I apparently looked at him a little cross-eyed, as if in disbelief. After all, he hasn't come behind and read my putt. Rush looked at me and said, "Man, I've been readin' these greens for foty three years. Two balls to the right." I settled over the putt, and figured I'd hit it straight at the hole -- I couldn't play the ball outside the hole left, my brain just wouldn't let me. Hit a perfect putt, perfect speed, and the put broke. . . two balls to the right. After that, I just let Rush tell me what the ball was going to do.
Billy (last name unk) at Evanston, again about 15 years ago. After 3 swings, Billy told me yardages and picked clubs for me, perfectly, for the rest of the day. . .