Stephen Michael Molesky

Stephen Michael Molesky passed away suddenly on the morning of July 1, 2025, while doing one of his favorite things — walking in the quiet of the morning, taking in the beauty of nature.

Known affectionately as Cool Steve, Steveo, Daddio, and PopPop, Steve lived a full, vibrant life centered around the people he loved most: his wife of 53 years, Carole; his children, Kelly (Eric Simental), Tara (Jordan Wilson), Ryan, and Lindsay (Jonathon Stroup); and his beloved grandchildren — Niko, Christian, Tyler, Ava, and Carmella. He is also survived by his brother, Michael (Kathy) Molesky; sister, Patti (Ted) Lempke; and many dear friends and extended family. He was preceded in death by his parents, Mickie and Lois Molesky.

Steve was the kind of person who worked hard and played even harder. He built a successful financial business in 1995 — a career he loved because it allowed him to help others live comfortably and plan for their futures. His dedication to his clients and passion for his work never waned. Over time, his business became a true family affair, with three of his four children joining him. Kelly and Lindsay continue to work in the business, which was recently purchased by his son-in-law Jordan. Steve remained involved because as he often said, he loved his clients and “it’s not work if you love what you do”.

His passions were many — and uniquely his. He had an eclectic love of music, from Golden Oldies and Beatles Brunch (a Sunday morning staple in the house), to Motown, the Rat Pack, Irish ballads, Gloria Estefan, and Hawaiian tunes. He collected coffee mugs and t-shirts with pride, traveled often — especially to his beloved Hilton Head and Hawaii — and never missed a chance to root for the Redskins.

He had a special talent for guarding lounge chairs at Marriott pools, and an even greater one for cheering on his grandkids at their games — often turning into an unofficial coach on the sidelines, famously shouting his signature: “PIVOT!”

He believed in staying healthy, not just to feel good but to keep up with the grandkids and make it to Hawaii at least ten more times. His routines included walking, tennis, swimming (only in Hilton Head), yoga, aggressively eating two apples a day (keeps the doctor away) , oat bran muffins, and — of course — Hula pie.

Steve’s sense of humor was unforgettable — sometimes wildly inappropriate, always hilarious. He had that rare gift of lighting up every room he walked into, whether with a perfectly timed fart joke, a wild story from his travels, or a spirited toast with a beer or Aperol Spritz in hand, punctuated by his signature “Up yours!”

He was unmistakable in his look: bright red sweatpants from 1981 (held up proudly by suspenders), surrounded by a personal archive of coffee mugs, bags of nuts, t-shirts, and old magazines. A true creature of habit, Steve booked all his travel over the phone — and somewhere, an agent at American Airlines is definitely missing him right now.

He brought joy, mischief, and unforgettable laughter into our lives. And while the world feels a little quieter without him, we’ll carry his stories, his style, and his spirit with us — always.

Though he didn’t always show it in conventional ways, Steve cared deeply. He went out of his way to help those around him — researching medical information, helping with job interviews, making useful phone calls (calling 1-800 number), becoming an Uber driver, and always sharing his favorite restaurants and travel tips. His acts of kindness were often quiet but deeply meaningful. He loved nothing more than to sit back and watch his family happily interact with each other.

We miss him terribly already: his contagious laugh, his voice, his fierce love, his big opinions, his silliness, of course his moustache, and the way he made life brighter for everyone lucky enough to know him.

He lived each day with intention, gratitude, and a whole lot of laughter. To honor his legacy, we plan to do the same — to live fully, love deeply, and never take a single moment for granted. And we encourage you to do the same.

As Steve’s favorite quote reminds us, “Carpe Diem.” Or, in his own words: “Carpe the shit out of the Diem.”

A Memorial Service will be held on Friday, September 19, 2025, at the Church of the Resurrection, 3175 Paulskirk Drive, Ellicott City, MD 21042 at 12:00pm, followed by a Celebration of Life at Kelsey's Pub, 8480 Baltimore National Pike, Ellicott City, MD 21043 from 1:00pm-5:00pm (Family and Friends can drop in anytime between 1:00pm and 5:00pm).

Memorial Donations can be made to the "Tunnel to Towers" Foundation , please check the box to Dedicate your donation in memory of Stephen.

Please consider making a donation to the Maui Strong Fund : "Lahaina was so special to Steve and he would love any contribution to helping out the community there."

Tunnel to Towers Foundation
2361 Hylan Boulevard, Staten Island NY 10306
Web: https://t2t.org/

Maui Strong Memorium
827 Fort Street Mall, Honolulu HI 96813
Tel: 1-808-566-5560
Email: donorservices@hcf-hawaii.org

You can copy and paste this link in your web browser or use the hyperlink above at the bottom of the obituary: https://host.nxt.blackbaud.com/donor-form?svcid=renxt&formId=c1212d85-8189-46e8-90a5-49348a397b31&envid=p-q80hWdJOQkGrNPxGPtgjtw&zone=usa