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Family Tree / Business

Caffrey Tree and Landscaping has its roots in Scotch Plains since 1978, with the second generation now enjoying the fruits of success.

Bob Caffrey, 68, calls himself a Scotch Plains boy, despite his current residence in North Plainfield. He grew up in town and lived there until he was 30, and he started his business there, Caffrey Tree and Landscaping, in 1978. Working for himself was a matter of practicality rather than passion, as he explained that, with both of his parents passing before he was 30 years old, he started his own business to make money and put his brothers and sisters through school. 

Approximately 25 years after the business began, his son Bobby, then 15, started working for him. At first, the boy was dragging brush and laying sod. It wasn’t until Bobby turned 18 that he began cutting down trees and working with chainsaws. Now 35, Bobby says he’s been doing sales, billing, management, and firewood delivery. “I wanted him to do every job so that when he went to sales he would know what it took to get the job done,” Bob said. The process was gradual and natural, but it was never forced. “My father said if I wanted to do the tree business he'd be very happy but if I didn't he'd support anything I did otherwise, so there was never any pressure,” Bobby explained.

It was, in fact, a combination of a labor of love for the boy. He’d tried other jobs, but ultimately, the family business was the best fit. “I always liked working outside,” Bobby said. “I did some bartending but didn't like the hours, and I had a financial job after college, but I’m not a desk job guy.” He was working for Major League Baseball when Hurricane Sandy happened, and his dad needed extra hands. Bobby was used to following his dad’s directions by then, as his father had been his coach in baseball, basketball, and football as a child. On the job, though, he learned from his coworkers. “They taught him the job more than I did, my other employees,” Bob said. “He knew how to talk to the men because he worked beside him for seven or eight years. He gives respect and commands respect by actions and you can't ask for more than that.” Bobby went on to become a licensed tree expert. He’s had his arborist license for nearly a decade.

In 2019, Caffrey senior was sidelined with spinal meningitis and spent two months in the hospital. Thankfully, his son was well prepared to step up. “My biggest compliment was when customers I had for over 40 years said, ‘We didn't know you were gone. We didn't know you were sick. We thought you were on vacation,’” Caffrey said. 

Outside of work, the relationship seems equally compatible. “There are no difficulties for us. We butt heads here and there but we get along really well so it works out,” Bobby said. “We try not to talk business on the weekends or at family things, and we do a pretty good job at keeping work at work.”

Bobby recently became a father himself. His son, Chase Robert, is a toddler now, but the future comes quickly. “If it's still a profitable, fun business to do, perhaps one day, he’ll continue,” Bobby said. Bob has other ideas. When asked if he’d want his grandson to join the business, he laughed. “No,” he said, “this work is too hard. I’d love to see three generations, of course! Who wouldn’t? But I’d love to see the kid use his brains, not his body. I wouldn’t push anybody into this.” It remains to be seen how far the apple will fall from the tree.

Recipe provided by Darby Road Pub;

Smoked Old Fashioned:

ingredients:

2oz Misunderstood Ginger Whiskey

2 Dashes Angostura Bitters

4 Dashes Orange Bitters

Spoon in Maple Syrup

Maple Bourbon Smoke Chips

Orange Peel Garnish