Sheffield’s Bacon Wrapped Pickles

Mike Sheffield and I were born on exactly the same day and are only about two hours apart in age. I’ve known him since the early 1970s on the San Antonio McCollum High School football team.

Mike was quite the athlete. One of my favorite memories of being part of the Cowboys football team was watching him run, upside down with legs in the air, on his hands.

In the late 70s and early 80s, we worked together building H-E-B Food/Drugs stores and shopping centers all over Texas. I returned to H-E-B later and Mike worked with me again when I became head of their Facilities Management Department in 1986.

I’d tease him about being so much more mature than he is because I’m his elder–by two hours.

Mike and Jack in 2009.

In actuality, Mike has always been a skilled craftsman and walking encyclopedia. He’s known for finding off-the-wall mom-and-pop eateries throughout the state.

To this day Mike continues to work at H-E-B overseeing facility and equipment warranties. He’s been a loyal and trustworthy employee for well over 40 years.

On occasion, we’ll take a quick roadtrip to the Texas Hill Country or someplace in the San Antonio area to taste a new “culinary find.”

Usually it’s comfort food, something like a chicken fried steak or cheesy beef enchiladas.

Mike and I are two big old boys who both pretty much like anything wrapped in bacon–corn, jalapenos, asparagus. You name it. We like it.

I love this guy as if he was my own twin. In honor of Mike Sheffield, here’s one of his typically unusual comfort food recipes: bacon wrapped pickles. Of course, all of the ingredients come from H-E-B.

Celebrating our shared birthday, Dec. 5, 2019.

Although perfect for game day or any time of year, we don’t need a special reason to enjoy them. He tends to use H-E-B brand thinner slices of bacon as it’s easier to manage. We like our bacon crispy, so adjust accordingly if you don’t. We’ve served it with ranch, blue cheese, and even thousand island dressing. In a pinch we’ve eaten (and enjoyed) it with just mustard.

It takes about 30 minutes to prepare and cook. The both of us together can eat more than this, but it’s adjusted for normal appetites.


  • 8 pickle spears
  • 2 ounces cream cheese, chilled
  • 8 slices bacon
  • ¼ cup ranch dressing


  • Preheat the oven to 400 degrees F (200 degrees C). Line a baking sheet with parchment paper.
  • Pat pickles dry with a paper towel.
  • Cut cream cheese into 8 strips.
  • Place 1 strip onto each pickle, and wrap with a strip of bacon, securing ends with toothpicks.
  • Place pickles on the baking sheet.
  • Bake in the preheated oven until bacon is browned the way you like them, 15 to 20 minutes. Let cool slightly, then serve with dressing.


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