The Senior Tour in 1986 started with two tournaments in Florida. I drove there from Massachusetts to caddie for Bruce. There was an unofficial tournament in Houston, TX in March. I was on the bag for Bruce’s first win on the over 50 circuit. As a side note, this tournament featured “celebrity amateurs” in the Pro-Am. To my utmost delight our celebrity partner was Spanky McFarland of Our Gang/Little Rascals fame.
I was on the bag for Bruce’s second win at the Benson & Hedges Invitational in San Antonio, TX. At the previous tournament in New Mexico I was told by Bruce that he would be using a caddie from his days on the PGA Tour at the upcoming tournament in Philadelphia., the week after San Antonio. In anticipation of this, I arranged to caddie for Gene Littler in Philadelphia. During a practice round in Philadelphia another player looked at me on Gene’s bag and said ” you won last week and lost your job?”.
The other caddie only worked for Bruce for one week and Bruce did call me and ask me to caddie for him again but I decided to stay with Gene. ( My good friend “Cowboy” hooked up with Bruce and won 6 tournaments that year ).
I was on the bag for Gene’s win at the Bank One Senior Golf Classic in Lexington, KY, in a play-off with Miller Barber and Bob Goalby.
When I started on the Senior Tour many of the original black caddies from the PGA Tour were still working. Smitty, Rabbit, Mule, and many others. But the changeover was becoming evident.