The Caddy

The real title of today’s offering is Every lesson I have used in my personal and business life, I learned as a caddy.  Now that title is longer than some of my blogs, so I shortened it to keep fingers from going numb as I typed.  A more frightening component of this title is that I have PowerPoint slides and an entire presentation based on this very long title.  I will spare you the brilliant oration causing multiple, time consuming standing ovations that occur when I present this live. Okay maybe more sitting ovations. Okay less ovations more looks of pure bewilderment hoping eventually I would get off stage.

During my WiFi free childhood, getting a job was a marker for independence.  I am not suggesting children moved out of the house at age 10 because they got a paper route, but I am suggesting that having your own money at a young age contributed to the local economy, especially in the candy area of the local general store.

After quitting my Globe and Mail paper route, I walked to the Oakville Golf Course and began my career as a caddy.  This was a decision with a clear financial upside.  Caddying had the potential of doubling my weekly salary. 

Caddies needed to show up at the golf course around 6:00 a.m. First caddy to show up was the first caddy out on the course.  2ndcaddy arriving was the second caddy out and so on.   On the weekends there were often 10 to 15 caddies waiting behind the pro shop, and most of them would get employment that morning.  More ambitious boys would hang around and get an afternoon bag.  I was so young I would use a pull cart and not carry the members bag until I got a little older and a little stronger.  The lessons from that period of time were universal and many have become the subtext of best selling books in the business section of bookstores.

Clear Expectations

At the end of every round, the member would fill out a caddy card to justify their payment.  On that caddy card there were more than a dozen criteria to measure the performance of the caddy.:  “Rake sand traps” “Stay quiet” , “Tend the Flag” “Clean clubs” etc., were all clearly displayed on the caddy card, to help the members assess the quality and skill of the young boy.  Every Caddy was aware of the expectations of the work. As we all learned later, with awareness comes responsibility. Caddies were slowly managing their financial potential.

Measure Performance

There were three levels of caddies at The Oakville Golf Course. The caddy card for “C” caddies was yellow, the caddy card for “B” caddies was pink and the caddy card for “A” caddies was blue.  “C” caddies received $2.50 for 4 hours of work.  “B” caddies got $3.00 and the coveted “A” caddies received $4.00 a round. Members were allowed to tip, and that was a pretty regular occurrence.  As you climbed up the caddy corporate ladder, with measured performance, you earned more money.  In caddying as in life.  Experience matters.

Develop Working Relationships

As time passed certain members would ask for certain caddies, and violate the standard order of 1stcaddy 2ndcaddy behind the pro shop. I became the steady caddy for Don Green and had guaranteed work three times a week.  A relationship of trust developed.  My eventual “A” caddy status gave me new confidence.  I could “club” Mr. Green.  I would share “You should use your 7 iron here” and a conversation occurred and collaboration on the course became the new norm.  Mutual trust was the anchor for this growing working relationship.  

Manage your Manager

The Oakville Golf Club will turn 100 years old this year. In those 100 years they have only had 5 Head Golf professionals.  Les Louth, Jack Davidson, Dave Clayton, Bill Bevington and recently Matt Maiola.  I have known all of these gentlemen.  (I recently visited The Oakville Golf club so I could claim I met every pro)  After caddying I worked in the back shop, cleaning clubs, eventually working in the pro shop for my entire time I was in school.  The three club professionals I worked for, Jack Davidson, Dave Clayton and Bill Bevington could not have been more different in approach and personality. I learned very quickly that whatever is important to your boss, will become important to you.  All of these men were highly principled and fair to their employees.  I honoured their unique approaches and worked hard to fulfill their individual expectations.

Adapt to Change

My early days of caddying were highlighted by getting to caddy for the Baillie brothers.  Aubrey and Frank Baillie golfed every Saturday and Sunday morning and paid their caddies $5.00 regardless of the caddy ranking.  Caddies would celebrate when they were selected for their bags.  This worked out well until the Pro Shop began investing in Electric carts.  That technology changed the caddy’s future forever.  I started cleaning clubs for free knowing that if I was going to work at the club, I had better change my job description.  Jack Davidson noticed my free help to the back shop and eventually hired me as the back shop club cleaner.


Caddies were given permission to play the golf course early mornings as long as they were off the golf course by 8:00 am.  I cannot tell you how many times there were 20 caddies on the first tee before 6:00 a.m. to ensure all 9 holes were played before 8:00 a.m. Earlier I mentioned Les Louth, the original Head Professional at the Oakville Golf Club.  He lived across the street from The Oakville Golf Club and had a lifetime membership at the club because of his decades of contribution.  Well Mr. Louth would walk the course every morning and would give caddies free golf lessons as they played .  He showed proper grip, swing plane, stance and other tips for free to ever 11 year old playing early morning golf.  He volunteered his time because that is what the good ones do.

Life Isn’t Fair

The club championship was the pinnacle of financial opportunity at the Oakville Golf club.  For that weekend caddies would get a bag and make more then $20.00 dollars for the weekend work.  One year I got to caddy for Cliff Post, Sandra Post’s (LPGA Major champion) dad, and he was a superb golfer.  He was a character and a wonderful man to know.  That weekend he finished 2ndin the club championship and while other caddies received their $20.00 bill, I got $6.00 for the weekend work.  It was simply an oversight by Mr. Post who later compensated, but at the time I was devastated.  I did not complain, pout or have a caddy temper tantrum.   I learned one must deal with disappointment with maturity and grace even when you are twelve years old and this painful lesson has served me well.

The 90 \10 Inverse Rule

During the 12 years I worked at the Oakville Golf Club the greatest lesson I learned has repeated itself in every organization I have worked for.  90% of the members I had the pleasure to work with were decent, kind, modest and virtuous human beings.   10% of the members were absolute unpleasant people.  Complaining about their clubs not being clean.  Complaining about their tee times. Literally complaining about everything.  Now I learned discretion and will not name these people, but every member knew who they were.  This 10% of the people caused 90% of the problems at work.  That ratio has proved consistent during my work and family life. 

The People

Finally this simplest life lesson I learned.  Reflecting back at my time at the Oakville Golf Club and my over thirty years in the corporate work world, one truth has never changed.  It is never the work you remember.  It isn’t the projects, the deadlines, the occasional promotions or even the annual financial bonuses.  No it is always the people you remember.  This is not an original idea, but it is an accurate one.  When I think about the Oakville Golf Club I smile, because of the wonderful people who shaped my life.  The greens keeping staff, the kitchen staff, the other caddies and the members.  In this current Covid19 world we are constantly reminded about this universal truth.

I have more thank exceeded my typical 1000 word count with this blog.  90% of you will forgive me, demonstrate empathy and understanding for my wordiness. As for the other 10% … F$^k  em!

Cue the Blong: More painful life lessons..



13 thoughts on “The Caddy

  1. Wonderful post Dennis. Full agreement on all points. One of the reasons golf is such an attraction for me is how well it serves us in all the areas you mention. I did a presentation once at a sales training meeting about how much you learn about people by playing golf with them. Let’s share slide decks someday. 😎👊

  2. Yes, I remember the hard working caddies. I was working as a waitress in the Club house at the Oakville Club. It was a big step up after picking strawberries at the Post family farm.
    Rode my bike to get there.

  3. I read this with a smile, and thought of my days at Hamilton Golf Club. When I caddied there, the GM was a Mr. Potter. One day when I was caddying for Dr. Bazoin, another member asked “So, are you Mr. Potter’s son?”
    I learned that not all private club members were that bright. Of course I said “yes” and wondered how he knew my dad, until the others set him straight.
    Dennis, apparently learned a lot more than I did.

  4. OGC – OMG. What a blast from the past. Great memories Dennis.
    I spent a couple of years caddying there as you probably recall. I caddied just after you, so, as time passed, the caddies showed up earlier and earlier to get work. I remember you had to show up crazy early by 5 or 5:30 am just to get ahead of the next guy or you did not work many days. It was dark when you got up. It was dark when you left your house and it was dark when you arrived. Nothing was open and nobody was there. The caddies were always the first ones to arrive to stake their claim. Sometimes you showed up at 5:30 am and you still didn’t work. You would sit around all morning until the afternoon doing nothing hoping you might get out – and then finally go home, bored, tired and disappointed.
    You and Dan worked in the Pro Shop by then and were gods to us caddies. You guys were fixtures and upward mobility was limited. But you were fixtures because the members loved. You guys were so witty, charming, irreverent and funny with them. I used to marvel as you would often so subtly insult the members to their face with a wry twisted sense of humour and get away with it – and they loved it too which I found both equally amazing and puzzling. I could never pull that off. Such hutzpah.
    When caddying was slow, I still remember shagging balls. You stood out in the field over beside the 9th/18th hole while guys hit balls at you. I think I was about 11 or 12 the first time. They gave you a baseball glove and a bucket and told you to go stand a couple hundred yards out while they hit golf balls directly at you. My first thought was WTF, this is insane. I finally realized that you were the pin and they were actually TRYING to hit you. LOL. You could not see the ball at all when it was first hit and the first instinct was to duck into a small ball or put the glove over your head for protection. We were told to open our eyes and just look up into the sky and that you would pick the ball up at some point. So hard to do. What a leap of faith … but it worked. Afterwards, these millionaires and billionaires (Oakville’s oldest and stagiest money – the Bailey brothers, Wilf Rudd …) or Rooster or old Clayfish himself would pay you $0.75 or $1.00 to do that. It was still better than just sitting around bored … but just barely.
    Yes I recall getting paid $3.50 to $4 to carry their bag for 5 hours for 18 holes and tend to their every need. And if you were very good, these pillars of society, these barons of industry, wealth and influence, would tip you $0.50 or a buck. Ooooh! And I recall you HAD to CARRY the bag. No carts. What is the point in having a caddy if he’s going to pull a cart we were told. No self-respecting caddy would do that. So much peer pressure. I remember guys that were 12 or 13 years old slumped over by the persistent 5-hour droning weight of those ridiculously and unnecessarily huge bags coming down the 18th fairway, at the sight of which all the sitting caddies would jump up and laugh and point and yell, “HE’S CAVING IN! HE’S CAVING IN!” – usually lead by Donald Stuart – until you or Danny would come out and yell at us and tell us to shut up. I just remember you or Danny were always yelling at us for something – though probably deservedly so. We were pretty convinced you hated us all – though probably deservedly so. It was all somewhere between a Norman Rockwell painting and something right out of caddy shack.
    Free golf in the early mornings was such a bonus – especially at that age. We started so early you could not see your ball beyond 50 yards or so. You just had to get a general direction that the ball headed in and walk in that direction hoping to find it. You had to keep moving too to get finished in time, so looking for a wayward ball was not a luxury we had. So we always played with crappy balls, not that we could afford new, or even newer, balls anyways. We would play with old Star Flites or Kro Flites or something you found in the woods, even if it had a big smile in it from a previous errant cut, something you could part with and keep moving. Our running shoes and socks were always fully soaked 10 minutes in. I remember playing on those early morning greens covered in dew before they were cut, with the rooster tails of water shooting up off your ball about 10-12 inches into the air as it hurtled across the green towards the pin, leaving a distinct visible line behind it. If you were lucky, you could putt second and follow somebody else’s line to the hole.
    But I mostly remember the smell of grass and the songs of robins early in the morning though – the first ones to greet us and meet the day there with us as the morning light broke. Such great fun and so many great, rich and cherished memories.

      • LOL, thanks Dennis. I remember that song too (thanks Greg Cheesewright) though perhaps not quite with the same rich and cherished memories as it was a very challenging time explaining to people why you changed your name. I hope you are doing well and still exercising that amazing musical gift of yours.

  5. I love your writing Dennis 🙂 It reminds of listening to you share your wisdom in casual conversations at team building events. I think there are probably many jobs that you can switch in for caddying if one didn’t have that life experience. For example… grocery store cashier/bakery assistant. Lots of people lessons there! Everyone should have these experiences before they get those cushy jobs in big business. 😉

  6. Well,Lo and Behold I never imagined I would find Dennis Ford and Bruce C anywhere except my memory
    I was in the very last caddy cohort at OGC, there were only maybe 7 boys golf mad enough to show up. We really just wanted to tee off at 4:30 and play 9 holes and scrounge for balls in the creeks. Golf became a lifelong obsession for me and I moved to Australia long ago but I never thanked you, Dennis for being such a good humoured guy, the only guy who ran the caddy tournament and I still have the plaque from the trophy you gave me. I hope Dan and Keith are doing well

    • Dave sorry for the late reply but only come on here monthly when I write a blog. So great to hear from you and wow what a history you have in your post caddy live. Stay well and stay safe. Sadly Keith passed away recently. Far too young.

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