Musings on ‘The Man with the Painted Cap’

I don’t have any memories that precede Sterling. The earliest, he’d give my little brother a block of wood and a piece of sandpaper when Bart wanted to help Sterling in his refinishing shop by the bowling alley. He maintained a small backyard flock of wild ducks that fascinated me. He was Uncle Sterling to my close friends Diana, Donny & Laura. It wasn’t until I opened The Square Pie that Sterling became a regular part of my life.  As most Sterling Stories go, it began with a lick of paint. He was a small man, and wore a noteworthy baseball cap, coated with several layers of paint. I remember it being green and perhaps red, but in later years, it was a pure blue. It must have weighed a good 20lbs. Practically a helmet.

Longtime Wilton resident Sterling Schwartz died Dec. 29 at Close to Home in Tomah. Rebecca (Orlikowski) Gagnon photo

I hired Sterling to paint the storefront at 400 Main in the spring of 1997. As I looked out the big front windows, I could only see the bottom half of the ladder, but I realized that he was moving the ladder, from the very top, by hopping it and shifting laterally along the cracked sidewalk, almost like a po-go stick. When I scolded him for such practice (OSHA would not approve!), he told me that he was charging me by the hour and that it took much, much longer time for him to climb down, move the ladder, and climb back up, so I should just be quiet about it; and so our relationship began. 

By way of barrels worth of cups of coffee and loaves of toast, he was a regular at the Pie. He was invited to tables of friends and quickly became part of the group. The regular delivery drivers, lawyers and bankers would ask, “Where’s the Man in the Painted Cap?” and we’d tell them that, “he’ll be in soon.” Sterling told stories and shared the local gossip with customers, staff and myself. He introduced me to the old-fashioned drink called Postum; a malty coffee substitute “popular” during yesteryear. He would tell us how smart his dog was; a pure-bred mutt that could do tricks and sing harmony with Sterling. He’d bring us flowers, making the young staff blush. Old newspaper clippings were often brought for show and tell. Alvis Strazdins and Sterling were a dangerous pair that could dream up schemes, some brilliant, some on the verge of delusional, to pass long winter afternoons: an advice column, for this newspaper: Ask the Man with the Painted Cap, was an idea that should have been brought to fruition. Best was The Widow of the Week Program, a plan to accomplish small tasks in an elderly woman’s home in exchange for delicious meals and warm beds for this certain bachelor never had a chance to flourish. Alas.

Every town has their characters. Some that you would rather not know, others you’d wish to have known more. Sterling will go down in my small-town history book. Yet I will never be able to capture the wisdom, the gentleness nor the character of The Man with the Painted Cap.

Best, Gina Rae, Goddess of Pie

Comments are closed.

  • Strains of spring 

    March 22nd, 2024
    by

    Brookwood Junior/Senior High School hosted its spring concert Thursday.  Esther Wooten and Drew Powell provide percussion for the senior high […]


    Pretrial conference for Barton yields no updates, more charges possible

    March 22nd, 2024
    by

    Monday’s pretrial conference for former Wilton clerk/treasurer Leigha Barton, who was charged in January with counts related to embezzlement from the village, resulted in no new developments, according to Monroe County District Attorney Kevin Croninger. 


    Royall hires new principal

    March 13th, 2024
    by

    Kole Huth will serve as the new Royall Middle School/High School Principal, the board of education decided at its meeting Monday. 


    Crowd attends meeting on Ontario development projects

    March 13th, 2024
    by

    No one quite expected the crowd of about 25 people to show up at Monday evening’s Ontario’s regular monthly board meeting. What drew so much interest was a hearing held about the new 12-unit apartment building under construction on Church Street.


    Kendall OK’s $2.1 million downtown project

    March 13th, 2024
    by

    Kendall approved a $2.1 million downtown (South Railroad Street) infrastructure project, which will occur in conjunction with the state’s reconstruction of Highway 71, at its regular meeting Monday. 


  • Norwalk police chief resigns

    March 13th, 2024
    by

    After nine years with the village, Police Chief David Jones submitted his resignation to the Norwalk Village Board, which it accepted at its Tuesday meeting. 


    N-O-W School Board approves expenditures, applications for college-credit program

    March 13th, 2024
    by

    The N-O-W School Board approved student applications to Brookwood’s fall college credit program totaling a little over $27,000 in tuition and materials.


    Wilton board candidates take part in reception

    March 8th, 2024
    by

    On Saturday, the Wilton Public Library hosted an open reception with the candidates for the Wilton Village Board.


    Royall boys earn first conference title in 11 years

    February 29th, 2024
    by

    The Royall boys basketball team clinched the Scenic Bluffs Conference title outright with a win over Bangor 53–37 on Feb. 22.


    Royall girls gain first regional title in 47 years

    February 29th, 2024
    by

    The Royall girls basketball team marked history in its program, as the team earned its first regional title since 1977.


    Wilton, N-O-W work out details of softball-field project

    February 29th, 2024
    by

    To refine an agreement allowing the Norwalk-Ontario-Wilton School District to use Wilton’s new softball field, school representatives met with the Wilton Village Board on Tuesday. 


  • Archives