I start by saying I had been golf mad since I was allowed to crap by myself and leafed through my father's golf magazines...(I thought the names and iconography were so attractive...Don January, Gene Littler, Miller Barber, Arnold Palmer;s umbrella logo, the Golden Bear, Merry Mex, Chi Chi Rodriguez, JC Snead, Ben Hogan clubs)
I turned 30 in 1997 and in April, after working around the business since I was 13, I had secured my first real "job"...as Caddiemaster at Rockrimmon CC in Stamford...
Environmentally, I remember how I felt the 87-97 period was a fallow one...Norman was always thwarted, John Daly held some promise (I still think the 95 Open win was as amazing as I ever saw) but I couldn't find any traction with the Strange, Simpson, Janzen , Montgomerie, Faldo, Floyd, Lehman, Nick Price days...there didn't seem anything so dynamic going on, so I was really primed for Woods after his amateur run and entry into Milwaukee right after... I was much more involved with the games of my players on the golf course...7, 12, and 16 hcps as they may be... I caddied for Siwanoy's fampus Sno-birds many times in over half a foot of snow.
It was also by this time that I started to see how the predatory puffery of swing coaches and video and new equipment held new fascination for people (remember VAS irons, Dave Pelz featherlites and the first Pittsburgh persimmon Burners?)...Ledbetter and Butch Harmon were now gurus...I had never ever heard of Scotty Cameron, but the first equipment controversies had already bubbled...the Ping Eye 2/box groove stuff.
I will say, that caddying had gotten a lot easier from 1987...Bushwhacker replaced Burton and then stands starting appearing and rain gear was finally something you didn't mind wearing even when it wasn't raining...but now local clubs were requiring bibs and some jumpers...
As for since, I'm sorta of the wrong person to ask...in 2003 my fiancee passed away under tragic circumstances, and slowly I found serving the golf of other people en masse (as a caddiemaster does) was unsatisfying...I asked what are they going to put on my tombstone: "He got member's out for play."? So I resigned in 2007, at age 40 I went back to school to finish a few undergrad credits and pursue an mfa with an inchoate idea to write about the game and teach others about writing...
Concurrently I was compelled to return to caddying and am able to enjoy the game in the guise of the player in front of me...the mass of it? the commerce of it? the industry of it? It's been good for pockets, but a destruction really. About 5 years ago, I guided a 24 HCP to a C flight President's Cup win against a 27 HCP...he won on #17 and played 18 to realize his lowest round, an 83 and was as happy as the day his daughter was married. That's about all it means to me and where its gone...the more commercial stuff that infuses the game, the more I retreat into these experiences, otherwise I'd barely touch the game again...
But I like talking about it here...for the most part.
cheers vk