Official Caddying Story: Jeff DiModica

Jeff DiModica has been President of Starwood Property Trust since 2014 and served as an external director of the Company from its inception in 2009 to 2014. In his current role, he leads each of the Company’s business lines including Large Loan Lending, Residential Lending, Infrastructure Lending, Property Investing, and CMBS Investing & Serving, which have a collective $18 billion of assets under management. Mr. DiModica was honored to be ranked in the top-10 of Commercial Observer’s “The 50 Most Important Figures of Commercial Real Estate Finance” list for the last 4 years. 

Mr. DiModica played on his state champion high school golf team in Melrose, MA, in 1981 and founded the Boston University golf team that is a varsity sport today. He has maintained a low single-digit handicap for 40 years but is 0-6 in club championship finals and looks forward to turning 55 in the spring to finally compete in the seniors! His only “gold-paint” hangs in the ladies locker room at La Gorce CC in Miami Beach where he and his wife Kay are the reigning net husband/wife champions. The Golf-Gods have spoken.

At which golf course did you first caddie, and how old were you when you started?

Bellevue Golf Club in Melrose, Massachusetts and I was 10 or 11 caddying for my grandfather.   

If I told my golf-snob friends it was a 9 hole course with a 117 slope and 68 rating, they would miss what mattered. Everyone knew everyone and everything about them, good and bad. Bellevue is a working class club in a working class town a few miles north of Boston, whose members were stars in the neighborhood, and lesser known outside of it, but that didn’t matter to any of them. They had Bellevue.

Tuesday night league was a weekly hall pass, and a Saturday morning tee time meant you would be home by dinner. The bar was inside the men's locker room back then, and when the phone rang on a Saturday afternoon, the men would go quiet wondering whose wife was calling. The bartender would likely say, “He just left,” as he pointed to the missing husband, who would either order another round or run for the door. I remember telling a member that his son's baseball team just won a playoff game, and everyone toasted him as if he had just made a 10’ slider on 18 (today we would wonder why he wasn’t there). 

It was the kind of course where Men would show up at 7am to make tee times for the following weekend, then sit on the balcony for hours with coffee and Dunkin’ Donuts commenting on everyone’s opening drive.  Where you talked about tournaments for weeks before and months after, and where a hole-in-one was celebrated like a world cup win. Everyone at the bar looked at you when you walked in, waiting for you to announce your score after which there was generally a comment, often a cheer, and frequently a bet to settle. The food didn’t matter, the guys in the bar had fresh meat walk in the door every 8 minutes.

Handicaps were monitored by the masses. People would comment as the assistant pro update the ½” plastic white numbers on the handicap board in the men’s locker room every 2 weeks when the GHIN printout came off the dot-matrix printer.  

I have belonged to better known clubs since, but never a better one.  Bellevue was the center of my teenage life, and the members my surrogate family.  I may have learned a few bad habits, but I met and learned from some of the most genuine and entertaining people I have ever encountered, with names like “Whacka” or “Long Ball”. I learned how to be seen but not heard there, and later I learned to drink and tell jokes there…life skills I never knew I was learning until I did. I was intoxicated by my indoctrination to life as a man, and surprised at how similar it was to life as a teenage boy. 

If I wasn’t caddying, I was chipping or putting for quarters with members or playing pool for hours to be around these guys. I heard every story and knew not to repeat them. Houses were small in Melrose, and most members lived within a few blocks, so the club was the big living room most of us didn’t have. To my mother’s disappointment, coming home from college, my first stop would always be the club to see my extended family.

Why were you compelled to become a caddie?

I started in the pool café at Bellevue when I was 12 or 13, but you weren’t allowed to caddie until you were 14. When I was 11 or so, my grandfather would take me to the club to caddy for him in the afternoons. He wore a tie under his sweater and was a true gentleman. A working class Reagan Republican. He gave me $5 a round and taught me the game, and how to caddy. It was a fraction of what I could earn cutting lawns, raking leaves or washing cars, but I loved that club and would take any opportunity to be there.  One day we were on the 5th hole, the furthest point from the clubhouse, and I threw a club in anger. He told me he was driving in and I could walk back. I never threw a club again, and will never forget his disappointment, or the lesson he gave me in how he dealt with it.

Take us through your first day on the job, who was your first loop?

High school and college kids dominated the caddyshack, and when I turned 14 in the spring of 1981, I showed up for weeks without getting out much. Bellevue didn’t have a range but it had a small area where you could hit your own balls 130 yards down a steep hill into a field. Members each had their own shag bag, and the older kids hated shagging balls. Since I wasn’t getting out, I decided to bring my baseball glove and offered to play center field for $2 a guy. I ran more than the greenskeeper's dog and got hit a few times on sunny mornings, but I was meeting players and making enough money to buy all the sodas and Peggy Lawton ChocoChip cookies I could eat out of the shack’s vending machine. 

My first loop was with one of our best golfers and biggest personalities Dick Hughes.  He played fast and walked faster, and I could barely keep up. His bag felt like it weighed more than my 100 pound frame, and he could tell I was struggling with it and gave me a towel to put on my bruised shoulder at the turn (if you ever did this you remember adjusting it every 5 paces as the slippery thin leather straps slid off the towel hump).  I caddied for Mr. Hughes a lot over the years and tried to emulate his ground game. He was our Seve Ballesteros, a swashbuckling shot-maker with great hands who could hit a 7 iron close from any lie or distance inside 160.  He taught me it was “possible” to hit a high draw off a rock and through a 1 foot opening in the distant trees, a lesson that has cost me a lot of strokes over the years.

What was the biggest mistake that you made during your caddying career?

No one asked the kids to read greens no matter how good a player you were. The course was tree lined and hilly. While the players were putting, you would always leave a driver on the tee and run to forecaddie the next fairway (a lost art!). Bellevue had a keg behind the 6th green during tournaments, and I remember when I was 15 or so, I took a beer on the way to forecaddie 180 yards out on the left of 7, near the 9th tee. My player topped one 50 yards off the tee, and I had to run back up the hill with clubs banging in the bag, allowing an older member on 9 tee to notice I had left a beer behind. When he said something after, my player winked at me and said it was his beer that he asked me to bring down the hill for him. That was Bellevue. 

What did you most enjoy about caddying?

The camaraderie. Caddying taught you respect, punctuality, speaking when spoken to, and that women grow up, but men never do. I learned that men of every age tell the same bad jokes, and talk about the same things, girls, cars, sports, and why they hit bad shots. I learned to listen to endless excuses for which their playing partners had no tolerance for and to make excuses for them. That perfect fairway lie must have been in an old divot. That trap was raked by a blind man. That uphill putt must have been into the grain. 

I could beat most of them by the time I was 16, and loved when a player would ask my opinion and make me part of the match. I hated caddying for people who wanted a sherpa and not a caddy, and I have always tried to make my caddy feel like my partner since, regardless of their golf acumen. In my games today, I always tell the caddies on the first hole that the winning caddies get an extra tip, and my level of engagement drives some of my playing partners crazy. If it does, I just assume they never caddied.

Tell us about some of the people for whom you caddied, did any of them contribute to your career in a meaningful way?

Our members were hard working middle class and I learned more from them than I could ever pay back. I learned life isn’t easy, heard real life problems, and met honest people who uphold the sacred rules of golf more than most of the CEO’s with whom I have played with and been around since. You can’t control what happens to you in golf, and these people understood that. People who are used to controlling the things around them and getting their way are a lot more likely to bend the rules or use a foot wedge than those who have dealt with a lot of bad bounces.

What was the biggest lesson that you learned from caddying that helped you succeed as you progressed in life?

Keep up, don’t be late, don’t make excuses, speak when spoken to, and most importantly, shit rolls downhill. The more you say, the more you open yourself up for blame. Golfers want to blame something other than their swing, and in business, people do too. Choose your words carefully, and once your player or your boss settles on something, go with it, no matter how strongly you may disagree.

We didn’t have lasers, pin sheets, or distances on sprinkler heads in the early 80’s, so we would step distances off from the 150 yard markers. That leaves a lot of room to be second guessed. We had pretty sloped greens at Bellevue. As I became a better player, I would try to guide players to be below the hole, but that meant they missed more greens, which is inevitably the caddy’s fault. I learned that the middle of the green is the best target for tips and longevity.

 If you could nominate one former caddie who went on to enjoy success, whose Official Caddying Story would you like to hear?

Ed “Woody” Maher. Woody is a vice-chairman at Newmark, was a founding member with me at Gil Hanse’s masterpiece Boston Golf Club, and maybe the funniest guy I know…