Taking It To The Streets: Southampton Man’s Daily Running Streak Dates Back To 2015

Jonathan Jennings at Coopers Beach in Southampton Village at dawn. DANA SHAW

Jonathan Jennings doesn’t consider himself a great storyteller. He’s more of a “facts guy,” he says, someone who delivers information without much fanfare or embellishment. It’s a trait one could imagine serves him well in his job as the course superintendent at Shinnecock Hills Golf Club, where he is tasked with managing a large staff and caring for the more than 250 acres of hallowed ground that has played host to the U.S. Open five times (and will host for the sixth time in 2026).

In other words, Jennings just gets the job done, with speed, efficiency, and effectiveness. It’s an approach he takes to other areas of his life, including his hobby, running — although it’s far more appropriate to call it an obsession. When it comes to talking about running, Jennings should give himself more credit, because he has an almost endless stream of stories to tell, and the spare, matter-of-fact way he tells them only adds to their appeal.

Jennings, 57, only took up running in adulthood, but he has embraced it with an obsessive gusto. While he is a veteran of eight marathons and several half-marathons, it is his dogged, day after day consistency that is most impressive. By his count, Jennings has gone for a run 2,151 days in a row.

On January 1, 2015, Jennings began running every day. He joined Streak Runners International, an online community of runners committed to running at least one mile, every day, for as many days in a row as they can, exactly one year later — runners must complete a full year of running to qualify for membership. Jennings read an article about the organization in the Wall Street Journal, and didn’t wait too long to sign up. It made sense — he had already been running every day, and figured that joining the group would help him maintain that commitment.

Jennings has stayed the course since then, and has seen and experienced a lot, both before and since he’s joined. There was a run in the August heat near his former home in the Chicago suburbs that led to cramps and nausea so intense he needed to lie down — so he dipped into the nearby woods in order to avoid attracting attention for laying on the busy sidewalk. He’s run in a blizzard in Reykjavik, to the top of an opera house in Oslo, and has gotten so lost in Montreal that a 6-mile run turned into an 11-mile slog.

He’s had encounters with various animals — deer, skunk, and one aggressively confident rat; been questioned by police; run in towns and cities on both coasts of the country and everywhere in between, as well as internationally. And he’s done most of it in the dark, both because of a job that requires him to be well into the workday by sunrise, and because of a personal preference for running outdoors (you will not find him on a treadmill). During the week of the U.S. Open in 2018, Jennings was setting his alarm for 1:45 a.m. for his daily runs. Yes, you read that correctly. During what was surely the busiest work week of his life, Jennings was averaging around three or four hours of sleep each night, and only ran 1 or 2 miles on those days. What he likes about the Streak Runners Club is its emphasis on simply showing up every day, rather than on distance, although he’s impressive by that metric as well, with most runs at or close to the 10-mile mark.

“Running is a priority for me,” Jennings said in an interview in mid-November. “If I don’t do it first thing in the day, it can get away from me, and I want to be home at a decent hour.”

In the summer months, when the club is busier, Jennings is up at 3 a.m. to accommodate the longer distances he typically aims for — 8, 9 or 10 miles — and to be ready to report to work at 5 a.m. In the slower, colder months, he can “sleep in” until 4 a.m.

Many adults find ways to commit themselves to regular exercise routines, because they understand the physical and mental benefits it provides. They recognize the fact that prioritizing their health is a good thing, even though staying in a warm cozy bed on a frigid February morning is infinitely more appealing than emerging from the covers and pounding the pavement in sub-freezing temperatures underneath the stars. Doing that four or five days a week would be impressive enough, a signal that one’s willpower and penchant for self-discipline are uncommonly robust. Doing it for more than 2,000 days in a row begs a deeper psychological examination.

Jonathon Jennings

Jennings laughs when he is asked, in gentler terms, what is wrong with him.

“I think it’s just my personality,” he says with a laugh, freely admitting that his wife thinks he’s crazy. “I think I just wanted to take it to another level and just wanted to improve myself. I like challenges and I like having goals.”

In keeping with one of his core personality traits, Jennings likes the simplicity of running.

“It’s a good, compact workout,” he said. “It doesn’t require a lot of time, or a lot of gear.”

As for why he always runs outdoors, even in horrendous weather conditions, Jennings makes it clear he has a sense of adventure, and doesn’t like to stay put in one spot.

“I’ve seen some really neat places on my runs, parts of cities that I would have never seen,” he said — which brings us to the alpha rat.

During a February trip to Washington, D.C., to take his son, Ted, on college visits, Jennings went out for an early morning run, winding his way past the Lincoln Memorial, Washington Monument, and other major landmarks in the nation’s capital. It was dark, and there wasn’t much traffic because it was a Saturday. Streetlights illuminated the major roadways, but when Jennings turned off onto a side street, it was harder to see. He spotted something on the sidewalk, running toward him, fast. At the last minute, he realized it was a very large rat, seemingly undeterred by his presence. Jennings quickly bolted to the opposite side of the street to avoid it.

He had a similar experience in his former home, the Chicago suburb of Naperville. At about the 8 or 9 mile mark of a long early morning run, he detected what looked like a small animal, resembling a raccoon or large house cat. It was only until he was about 3 feet away that he realized it was a skunk.

“I basically jumped right out of my skin and straight across the street,” he said.
If, at this point, you are questioning Jennings’s sanity in much the same way his family does, you are not alone. His commitment to extreme early morning running has been known to raise the suspicions of law enforcement on occasion — he said he was once stopped by police during a long run and asked a series of questions about why he was out running at 3 a.m.

Encounters with police and unsavory wildlife are often the least of Jennings’s worries when he’s out for a run. There are the good days, of course, when the weather is perfect, the air is crisp, and his body is not betraying him in any way. But when you run more than 2,000 days in a row, there are plenty of bad days, too.

“I’ve run when I’ve been sick or injured,” he said. “Fortunately, that 1 mile I can usually pull myself through. I’ve run in blizzards; I remember going out one time and the snow was just blowing sideways, and there were 10 inches of snow on the ground. I barely made it out a mile and back.”

He said he’s been known to wear ski goggles for a run, and has come back with ice in his eyelids; he’s gone out in wind so strong it knocks one leg into another as he runs.
When facing conditions like that, being part of the online community of like-minded people helps. Jennings said other streak runners have shared stories of doing laps in airports or parking lots just to get in a mile for the day. Weather, illness, overscheduling, and a host of other factors can make it nearly impossible to complete even a one-mile run on some days, and Jennings said he has run through the pain of nagging injuries too, including tendon strains that made a mile jog harder than some of the marathon training he’s done.

“You just grit your teeth the entire time until you get back,” he said. “The best thing about running is that when you stop, it feels so good.”

Jennings has injured himself several times mid-run as well. Years ago, he was in Dallas, Texas, for a work conference. Several hours before he was scheduled to give a presentation, he went out for run and took a spill on the asphalt. He got up quickly and kept running, but soon noticed a feeling of warmth on his leg. He looked down to see he was covered in blood from where he’d ripped the skin off his knee when he fell. Jennings spotted a convenience store, went inside, and pulled a rumpled $10 bill out of his sneaker (pro tip: always stash a bit of cash with you for long runs) to buy some bandages. He carried them in his hand while he finished the 3 miles back to his hotel, then had to stealthily sneak past people in the lobby he was about to greet in a professional environment, hoping they wouldn’t notice the horror show on his leg, before cleaning up and donning a suit and tie for work.

Of course, Jennings has learned a thing or two about running outdoors in all kinds of conditions, and has a few tips (in addition to the cash-in-shoe pointer) for anyone who wants to stick to an outdoor running routine, especially as the colder months approach.

He’s found that running sneakers need to be replaced roughly every 300 miles or so — he goes through three or four pairs per year, he said — and added that less is more when it comes to clothing and layers, even in colder weather.

“You don’t dress for the first mile, you dress for the second mile,” he said, adding that he doesn’t switch to pants from shorts until the temperature hits the low 30s, although a hat and gloves are essential in cold weather. “The main areas that get cold are your fingers and head, so if you keep those warm, the rest is pretty good.”

Jennings doesn’t like to carry water with him unless he’s going farther than 10 miles, but he has scouted out locations with water fountains, like Cooper’s Beach. He listens to music while he runs, favoring anything from top hits to classic rock.

And of course, he has invested in a reflective vest, and always makes sure he runs against traffic, because of how frequently he runs in darkness.

Any obstacles Jennings has to overcome to get his runs in — and clearly, there are many — are worth surmounting, he says, because of what running every day does for him not only physically, but mentally, especially in these extraordinary times.

“I work a lot of hours, so it’s not just to stay fit, but it’s for mental balance, too,” he said. “A morning run wakes me up, and it really makes a big difference.

“It allows me to gather my thoughts, but also helps with putting the genie back in the bottle, so to speak,” he added. “I can start getting too many thoughts going at once, and running helps me put the cap back on it.”

With so much uncertainty in the world these days, the streak is more sacred than ever to Jennings.

Running has always been important to me, but even more so now,” he said. “I’m leading a group of people at the golf course, our maintenance staff, and being able to keep them healthy and think clearly about how to manage all that is really important.”