“The Outlaw’s Back Story”

The Forest

Jesse James was born and bred in Richmond, Virginia. The youngest of five children birthed by the honorable Judge Olivia Masterson James. And if having a judge for a mother wasn’t enough to blow the burrs off his ass, his father, Redmond James was the premier defense attorney in the great state of Virginia. So while the dinner table conversations were fantastic in the most comprehensive sense of the word, the day-in and day-out running of the James household was managed as tightly as the Supreme Court. That is to say there were schedules and expectations and rigid systems set in place to keep five children on the straight and narrow.

Good grades were anticipated and moderately praised. Thank goodness his folks didn’t have a dummy in the bunch. The James kids were natural-born rule followers and heavy hitters from kindergarten on up.

Jesse’s sisters, Molly, Lacey, and Abigail—the middle three—all got along with each other. Not a moment of jealousy between them. His mother attributed this to completely different styles and taste in clothing, friends, and activities. Each had different gifts, hobbies, and goals, so they rarely competed for anything.

Jesse’s brother Duncan—the oldest—was exactly as his mom’s friend Rita described him. “As well-brought-up as a man could be.” And, after achieving honors in all things, Duncan went into the family business—sort of. Not a judge or a trial attorney but a corporate lawyer with an MBA. Still, his parents thoroughly appreciated Duncan’s initiative, his reasoning skills, his overall competency, and his choice in his bride from Henderson, North Carolina. But that’s another story.

Jesse—the baby—didn’t lag behind his brother in the smarts department. Prep school wasn’t necessarily a breeze but it wasn’t too much of a challenge either. He put in the time because he didn’t mind reading. Besides, in an effort to stay relevant at the dinner table he needed a vast vocabulary and the ability to put his thoughts into words—and then back them up. Staying pertinent in a household consisting of two lawyers and a handful of overachievers was Jesse’s mission from Labor Day through Memorial Day.

But once summer hit, all bets were off.

Every June the James family packed up and drove three hours north to a tiny haven outside of Annapolis, Maryland. An ideal summer setting perched on top of a peninsula overlooking a scenic river. Three hundred cottages nestled anywhere from the edge of a cliff to the bottom of a ravine deep in the woods. The summer residents affectionately called it the Forest.

In the early years there were old brown gates and a man named Smothers who manned them. Nowadays, those beautiful stone gates were merely symbolic as you entered the shaded grove, coaxing deep breaths and the peace of having finally, once again, arrived home. Further down the road a more modern guardhouse stood mostly unattended with the addition of a one-armed security gate that would raise and lower if you punched in the proper code.

From the age of six, Jesse along with his parents and siblings, moved in with their paternal grandparents in their summer cottage and enjoyed the freedoms and activities their own father had experienced during his youth. For young Jesse, swimming, boating, a camp program that rocked, and the best friends a guy could find in a lifetime all came together from June until September. And the time would fly.

Boy, would it fly.

Most of his summer friends spent their school year in DC or Baltimore and, unlike him, their parents actually resided in the Forest during the week—the commute to work in those cities being relatively easy. Due to their work in Richmond, his parents drove up Friday evening, spent the weekend joining in the festivities (and there were always festivities), and then left early Monday morning for the drive back to their workweek. It was up to his grandparents—God bless them—to manage Jesse and his siblings during the week.

Grandmom was a damn good cook, even if her repertoire was limited. Tuna melts with dill pickles and chips, chicken fingers with real French fries from her old-school fryer, hot dogs covered in an assortment of toppings like cheese whiz, relish, onions, and sauerkraut, served with Rookie’s potato salad, tomato soup and grilled cheese, and twice a week, a more lavish dish from the crock pot. Anything from chili, to pot roast, to spaghetti and meatballs. The woman was busy in her own right, playing golf and tennis and putting together the adult talent show each summer. She didn’t have a lot of time to spend in the kitchen.

Each weekday morning Jesse would roll out of bed, brush his teeth, don athletic wear, grab whatever ancient sports equipment he might need—anything from a badminton racket to a ping pong paddle—and ride off on his bike to flag raising. The good ol’ red, white, and blue was raised to the sounds of a trumpet, the pledge was recited, and one camp group would sing the camp song to start off the day. After his morning session, he’d return for a quick lunch, usually bringing a friend or two with him, and then they’d head back out for sessions two and three—anything from a nature hike to crafts to archery but always one session of swimming daily. Living on a river it was important everyone knew how to swim and swim well. At the age of twelve, the kids in camp took the Red Cross Life Saving course, repeating every year after. After dinner each night, Jesse would be back on his bike racing around, or grabbing a bag of ancient golf clubs and setting out to play the nine-hole, sand greens course.

When Jesse was little, his favorite camp activities were horseshoes and kickball. On the weekends, he attached himself to his PopPop’s hip so he could be on the man’s powerboat where he learned how to clean and tend the ropes. He was fascinated with the way the rope tightened on the cleat and the knots needed to tie buoys to the bow. Even at a young age, he liked having his hands on the wheel, steering the boat, standing on a plastic footstool with his grandfather behind him.

When he got a little bigger, he fell in love with tennis and soccer, still spending time with his PopPop on an even bigger boat, now able to do the driving himself. He studied up for the Power Squadron course his grandfather wanted him to pass before he had permission to take the boat out on his own.

At thirteen, someone put a lacrosse stick in his hands and from that first moment he was all-in. A natural. He just got the game. Like he’d been reincarnated from a Native American and born with a stick in his hands. He could run for days, shoot between a goalie’s legs, win any face-off, and pass behind his back.

Lacrosse was his first love.

Five years later, Elise Thompson became his second.

To be continued …

Contact Us

Henderson on your mind? I'd love to hear from you.

Not readable? Change text. captcha txt