As a longtime member of the Country Club of Fairfield before leaving several years ago, I remember when we faced something of a quandary in the late 1990s. While our nearly century-old association on the southwestern Connecticut coast possessed a rich caddie tradition, we were having trouble providing golfers with more than a handful of competent loopers each season. So, we began looking at ways to remedy that situation.
Our first decision was to reconstruct our caddie yard by stocking it mostly with high school and college-age kids, the thinking being we could better avoid the problems that often cropped up with the older caddies on which we had been relying. And we liked the idea that by taking the youth route, we also would be giving back to the community where the vast majority of our members – and loopers – lived.
With that basic concept in place, we began to look at the best ways to execute it. Fortunately, we already had a number of key pieces in place, notably: broad support for reimagining our caddie program among club leaders and members; a head golf professional who had received his start in the game as a caddie and appreciated the benefits of such an initiative; and a caddie manager who taught at the local high school and not only had access to a vast pool of potential caddies but also knew which ones might be the best fit for our club.
Still, we were not sure how successful our attempts at attracting youth caddies would be. For one thing, the fees golfers traditionally had paid loopers at Fairfield, which in those days still took pride in its Yankee frugality, were modest at best. And given that they operated as independent contractors, caddies did not have set hours or receive any benefits. So, we decided to create a scholarship trust for them in hopes that the prospects of procuring thousands of dollars in financial assistance for college would be especially enticing. We also strove to keep the application process simple and put most of the emphasis in assessing candidates on academic achievement, citizenship and their skills, reliability and work ethic as caddies.
Financial need was a consideration, to be sure. But we believed that with the rising costs of higher education, every student could use some help. And what youngster, no matter how much money his parents might have, would not benefit from the empowerment that came with being able to defray some of those expenses on his or her own?
One of our early scholars caddied regularly for me through high school and college. After earning his undergraduate degree, he decided to go to law school, and the trust gave him money for that as well.
Our first year of operation was 1999, and we raised more than $200,000, largely from club members but also with support from our golf professionals, general manager and course superintendent. Some individuals became founding sponsors by contributing $5,000. Others wrote checks for $25 or $50. Whatever the amount, each donation was important and appreciated. And in addition to allowing us to initiate a modest endowment, those monies enabled us to award grants to nine scholars.
Enthusiasm for the program grew steadily, and so did the endowment as well as the number of scholarships we were able to mete out and the amount of each one. And these days, the trust is able to give substantially more money each year to about twice as many caddies as it did in 1999.
In addition to engaging club members, we encouraged former caddie scholars to contribute to the fund. And many did so. Some came to sit on the caddie trust board as well. We also created a caddie trust tournament, inviting those same individuals back to the club for an afternoon of golf with members. That turned out to be the time when we gave out the caddie scholarships each summer. For many of us, that day truly was the highlight of the season, watching these youngsters whom we had gotten to know over the years, wearing blue blazers and big smiles and holding envelopes with checks that would help pay for them to attend some of the best colleges and universities in the land.
As I consider where the trust was nearly 25 years ago and where it is today, I appreciate what a win-win situation it has turned out to be. In addition to receiving money for their educations, the caddies learned crucial life lessons on the golf course: when to talk, and when not to, for example; how to read people and interact with them; how to handle difficult situations, and difficult golfers (and the game certainly has its share of both). Members also made a point of mentoring caddies and were only too happy to assist with introductions and letters of recommendation when the scholars started to look for work after school.
As for members, we were afforded the chance to give back to our community as well as to the young people whom we had gotten to know through several summers of golf. And the pleasure of seeing them grow up and watching their confidence soar as they graduated from their schools and took good jobs in New York City and elsewhere was immeasurable.
Eventually, he went to work for a New York law firm and came back one year for the caddie tournament with three of his partners. We talked after play had concluded that day, and he tried to express his appreciation for all the caddie trust had provided. But his voice kept breaking, and tears filled his eyes.
I was equally as moved by the moment but somehow managed to say: “What you have given back by taking advantage of these opportunities means at least as much to us.”
It truly does. And I do not know of anyone who has been involved with the caddie scholarship trust at Fairfield who does not feel the same way.
Top: Caddie scholars at Country Club of Fairfield