Sikeston grad falls back on Bootheel roots in making 'The Show' in his own way

Twice each summer, Sikeston High School manages to find its way onto the iconic playing fields of Fenway Park in Boston and Yankee Stadium in New York.

No, former Bulldog great Blake DeWitt hasn’t taken to the infield at those two baseball cathedrals since the summer of 2011, however, Chad Jennings still does annually.

“One of the neat things that I get to do,” Jennings explained, “is the (New York) Yankee writers and (Boston) Red Sox writers play a baseball game twice a year against one another. We play at Fenway Park and we play one game at Yankee Stadium. It is such a neat opportunity to play baseball at these ballparks.”

Jennings, who has been covering either the Yankees or the Red Sox for various publications since the fall of 2009, proudly spoke of wearing his “Who let the Dogs out?” shirt each time, which commemorated the 1995 Sikeston basketball season.

“I like that I have pictures of myself playing baseball,” Jennings said, “at these neat places and I’m wearing a Sikeston shirt.

“Sikeston means a lot to me.”

Jennings was recently inducted into the Sikeston Public Schools’ Hall of Fame and Honor Wall and is completing his sixth season as a beat writer for The Athletic, covering the Boston Red Sox.

Earlier in his journalistic career, the 1998 Sikeston High School graduate spent seven years covering the New York Yankees, before spending a season reporting on the Red Sox for The Boston Herald newspaper.

As it turns out, you can take the boy out of his small town, but you can’t take the small town out of the boy.

“The best advice that I ever got,” Jennings explained of being a successful reporter, “is to not think of it as trying to build sources, try to build relationships.”

That is where a little Bootheel comes in handy, especially if you’re asking $140,000,000 man Trevor Story why and how he went 0-for-4 with two strikeouts against the White Sox on Saturday.

“You get to know people,” Jennings said, “and that is what helps you the most.”

Jennings has found that putting in the time to “get to know” the players and leadership of the Major League Baseball clubs, just as he would converse with a neighbor at Jay’s Krispy Fried Chicken, not only provides insight into learning the intricacies of the game, but results in great content to write.

“It’s not thinking about the people that I am dealing with as a number or thinking of them as someone who can help me with a story,” Jennings said. “It’s a person that I am talking to, and occasionally, that has helped me with a story.”

Regardless of whether that “person” has $140,000,000 in his bank account.

Though Jennings admits to being obsessed with sports (he used to compile notebooks with his projected starting lineups of all 30 MLB teams), landing in Boston with his wife (a Boston native), Ashley, and two boys, Chase, 6, and Jude, 4, and covering a professional sport on a daily basis, wasn’t part of some master plan.

“My dad (Dan) is a farmer (outside of Matthews and Morehouse),” Jennings explained, “I just assumed that I would farm. I had never really put any thought into doing something else.”

But his path in life broke like a cut fastball in the “eighth or ninth grade,” according to Jennings when he was given the assignment to write an essay.

“I just remember all of my friends complaining about having to write this two- or three-page paper,” Jennings said, “but I really enjoyed the process of it. I liked figuring out the words and what I was going to make it about.”

The odds of a former Bulldog student traversing the journey from Sikeston to Boston are infinitesimal, and quite frankly, Sikeston Public Schools ought to center a marketing campaign around that type of success.

And doing so about Chad wouldn’t be a bad idea, either.

As it turns out, there are two Jennings siblings, raised by Dan (a Morehouse High grad) and Dianne (a Sikeston graduate) working professionally in the Boston area, as Chad’s sister, Laura, a 1999 Sikeston graduate and 2003 Mizzou grad, also works in “The Hub.”

“She got her Ph.D. at MIT (Massachusetts Institute of Technology),” Chad said with a good dose of family pride.

Laura earned a graduate degree in a biology-related field from what many consider the most prestigious academic institution in the world.

“We always laugh that I have this interesting job, that occasionally gets attention,” Chad chuckled. “Meanwhile, my sister, all that she has done is get a Ph.D. from MIT.

“She’s doing very, very well.”

All of this begs the question: What is in the drinking water around Moore and Wakefield Avenues at the Jennings’ household?

“Sikeston means a lot to me,” Chad said. “Especially with my parents having grown up there, the (family) farm being there, it still feels like home to me.

“I still think of myself as a Missourian, and very specifically, a Southeast Missourian.”