History of The Bolles School




   It went up in six months, like an inspiration, on a river bluff 20 feet

high once owned by the colorful slave trader and cotton planter Zephania Kingsley.

    It was a surprisingly beautiful hotel with an authentic Castilian atmosphere.

    The year was 1926.

 Asked to render the effect of an ancient Spanish castle, architects Marsh and Saxlebye came up with a masterpiece of Old World lookalikes.And for tourists

who valued charm and dignity and repose, the developers shot the works. From

pecky cypress to broken tile, from parchment tones to old ivory walls. Who would have dreamed that in less than three years the elite San Jose Hotel would be on the block?

      Who could have guessed that within a decade its twin watchtowers and noble archways would advertise the merits of a fashionable boys military school?

     Richard J. Bolles, the flamboyant New York capitalist, had been in Jacksonville since 1908, with an office in the Bisbee Building on West Forsyth and residence at the Seminole Club. His secretary was Agnes W. Cain, a shrewd 36-year-old Cleveland businesswoman who had been with him during his heyday in Colorado. He died suddenly in 1917. Care of his estate went to Agnes Cain. 

    By this time Agnes was well established in local real estate and investment circles. She had also met young Roger Painter, who had started to work as an office boy at four dollars a week for Richard J. Bolles the year before the millionaire's death. They were married in February 1923.

     It was the eve of the Florida boom, the real estate and loan business looked mighty good, and when the San Jose Hotel opened on January 1, 1926, Agnes Cain Painter held the first mortgage of $200,000. A year later she held a personal property mortgage on all the hotel's expensive furniture, fixtures, and equipment. Little did she know that in just another year she would be filing a foreclosure action. But it happened. Agnes bought the hotel at a foreclosure sale on the courthouse steps.

    So what do you do with a million-dollar tourist hotel when the real estate market has just fallen out? You don't miss a beat. You form a corporation (Bolles Investment Company) and elect officers (Agnes Painter, President and Treasurer; Roger Painter, Secretary). Then you sell the hotel and all its fancy furnishings to this same Bolles Investment Company for $225,000 payable entirely in capital stock. Then you issue shares in the corporation and,since you and the Richard J. Bolles Estate own most of the shares, you end up with the controlling interest. You lease the property first to a hotel group that drops $100,000 in no time, then to the Florida Military Academy for three years.

     It wasn't long before Agnes and Roger Painter found themselves not only collecting rent from the Florida Military Academy but taking a keen interest in its daily operation. By1929,they began living on the school grounds.

   Thus, when the Florida Military Academy failed to meet its financial obligations and was given notice in the summer of 1932 that it would have to vacate by the end of the year, it was not hard for Agnes and Roger to accept the suggestion of local attorney John C. Cooper, Jr.: "Why don't you form a school out there? The community needs one."

Neither of them had a formal education. Nor a burning zeal to found an educational institution, for that matter. But they had become attached to the boys. Since it was a boys school, Roger, whose strong suit was in handling people, would be president and have "active direction of the administration and business management of the new school." Agnes would remain in the background as the unseen power. By special dispensation of the state, Roger would be part of the Florida militia with the rank of Lt. Colonel.

    Selecting a new name would pose no problem. What else but the name found on important documents connected with the hotel since its creation several years ago? The Bolles School.