Ok, we have to define greatest pin positions because the question of "fairness" comes into play, and do you care about it. For my response, I'll not worry about it one iota,
Playing the short par four fourth hole at Rolling Green, pin front in a USGA qualifier years ago, I had a ten footer for birdie, downhill. My fourth shot was a 90 yard replay of my 2nd shot to the green, and I hit what I thought was a good putt, I knew what was coming when I lined it up. Perhaps Mayday can talk about this pin!
Pine Valley, caddy tournament , same year as the infamous Crump Cup which we dubbed Bator's Revenge ( Dick Bator, then PV superintendent had been very upset by the 64 shot the previous year by Bob Lewis in qualifying). Dick figured the loopers deserved the same treatment as the top flight Crump field.
Every pin, was absolutely fiendish, e.g.
First hole: hanging off the green back right-----tees back!
Second: On the ledge far right, that right the ten foot ledge
Third: easy one compared to the Crump--- front middle
Fourth: Middle right on the hogback
Fifth: Furthest right hand back corner
this continued on every hole, greens at warp speed on the stimp. I would argue, and it would be a good one, that the set-up was harder than the aforementioned Crump Qualifier that Jay Sigel led that same year. for anyone that played in or remembers stories about that set-up, it truly was an exercise in terror as 85 made the championship flight!
Two pins I remember vividly from the Crump
and have probably never been seen again
#3 right front causing multiple four & five putts
and one withdrawal
#15 Front middle .
absolutely had to chip it from in front
or get lucky to save par
The caddy tournament, with the exception of number three, was set-up harder by Mr. Bator, causing some egos to
get back in line , mine included!