“You could write a book!” It is a refrain I’ve heard often at WT in 16 years. Well, I don’t intend to end my Thistletalk writing career by penning a book, but it does seem like a wonderful moment to share some of my favorite WT stories.

In Which Marty Listens, and an Important Decision Is Made

t was my fourth week on the job and I was scheduled to meet with our Board President, Marty Powell. Something was really bothering me and I was nervous about raising it with him. I took the plunge and explained that while I understood why the Board had decided to build a new Lower School building at the City Campus, it was evident to me that the school needed instead to build a new Upper School. I expected Marty to put me in my place. I was a brand new Head of School, and the Board was well along in its planning. But, characteristic of Marty’s gentlemanly manner, he listened.

The Upper School student population was too small, I reasoned. To offer quality comprehensive extracurricular programs and a positive social experience for Upper Schoolers, we needed to grow from 45 students per grade to 60 students per grade. Moreover, I continued, the Upper School was dispersed throughout our Pre-K–12 building, hidden from view and prevented from shining as our flagship division. And by the time they reached eighth grade, students who had arrived in Pre-K were ready for a new place, a new experience; they needed a bigger world to move up to, which would entice more of them to stay at WT. (That year, we were facing 52% attrition from eighth to ninth grade.)

When I finished, Marty said, “This is your school now, Gary. If you believe we need a new Upper School you need to convince the Board.” So I set out to make my case, meeting with individual trustees and preparing a proposal to present at the next Board meeting.

At that meeting, the Board agreed with me, and voted to change their plan. And we built our beautiful Upper School at the corner of Morewood Avenue and Bayard Street.

In hindsight, I see that Marty’s support was the most important moment in my tenure and arguably one of the most important in the history of WT. Because he encouraged me to take the mantle of leadership, the Board made a good decision that had huge impact. Retention of ninth grade students increased to 92%; demand for new enrollment in the Upper School has skyrocketed; each division at the City Campus now has differentiated space enabling it to define its program and community; and the quality of WT’s extracurricular programs improved dramatically, especially our athletics teams.

In Which The Puritan Takes a Journey

In the fall of my first year, I discovered in the back office of the Upper School library The Puritan, a bronze sculpture by the celebrated American Beaux-Arts sculptor Augustus Saint-Gaudens. It was a grand piece, but oddly enough no one seemed to know how WT had come to own it.

In those early days we were always bracing ourselves for unforeseen financial challenges that could threaten to knock us off our feet. One such challenge happened that winter, when our health insurance company informed us that our premiums were going to be increased to the tune of $70,000; when we calculated what the cost would be to our individual employees, we knew we had to do something to soften the blow, but the cash reserves just weren’t there.

We decided to engage Michael Malley, a highly regarded Pittsburgh appraiser, to assess The Puritan. He immediately identified the piece as part of the estate of the late Arthur Braun, who had been WT’s first Board Chair. Mr. Malley appraised its value at $60,000. When I told him we planned to sell it, he advised me to send it to Sotheby’s in New York for auction. He also told me that to guarantee the preservation of the sculpture we would have to have it professionally packed and shipped. Trouble was, the packing and shipping would cost thousands of dollars. With that, the door closed on the sale of The Puritan to raise the needed cash.

Weeks later, I was preparing for a trip to New York for a WT event, and my flight was canceled. I decided on a whim to drive, and gave Mr. Malley a quick call to see if there was any chance he could arrange for Sotheby’s to accept The Puritan. He did so, and with that, our problem was solved: I would chauffeur the sculpture to Sotheby’s myself.

That evening, I drove my Jeep Cherokee to school and recruited the evening cleaning crew to help me prepare The Puritan for its journey. We found an old box in the basement and lifted the heavy bronze sculpture into it; we stuffed the box with rolls of toilet paper, maybe 20 in all, to insulate it, and off I went. The next day as I approached Sotheby’s in Manhattan, a tall, elegant woman with flowing attire emerged from the auctioneer’s offices, followed by a team of white-gloved men in handsome uniforms, pushing a rolling table toward my Jeep. I popped open the tailgate as the agent and her uniformed associates looked with horror at the face of The Puritan peering out among the rolls of toilet paper. I have to admit, I was embarrassed.

Well, The Puritan went on to more dignified days. He was selected for the cover photo of Sotheby’s glossy auction magazine and was situated at the entrance as the guests arrived. He sold for $100,000, which covered the cost of our insurance increase and gave us a cushion of reserve.

In Which Barb Has an “Aha” Moment

The 2007 Boys Lacrosse Division II Championship game against Kiski School at Charles Knox Field at Quaker Valley will always be one of my most special memories of WT. Put aside the fact that I am a big lacrosse fan and that the game was intense, ending in a sudden death overtime win for WT. It was the significance of the team and this game that made it so important. And a remark made to me by the legendary Barb Holmes, architect of WT’s status as a performing arts powerhouse, made this winning moment even more important.

The team was a compendium of WT grown talent, a serendipitous influx of quality lacrosse players from other schools, and a group of athletes who wanted to play for Coach Darrell Schmitt.

The most interesting of them was the young man who would score the winning goal, Pete Buongiorno ’07. Pete was a transfer to WT from Kiski. His one-handed overhead hook shot that floated over the goalie’s stick and into the far corner of the goal was graceful and gritty.

The build-up to that moment as the season progressed had been tremendous. The community had rallied around this team of interesting personalities, and a sports scene had taken hold, the likes of which WT had never seen before. There were tailgates before, during, and after games; attendance ballooned at each match, culminating in an estimated WT audience of approximately 500 at the championship game. This was new for WT, a school that had had little history of athletics success. Few seemed to understand that sports teams could bring camaraderie and enthusiasm to a school community.

When Pete’s shot drifted into the far corner of the goal, a melee ensued. WT fans went hysterical with joy! In the midst of the excitement, Barb turned to me and said with a mix of wonder and jubilation, “I had no idea what a great sports team could do for WT!”

Barb was right, and we have seen more moments like this one since the spring of 2007, as many other WT teams—notably Boys Soccer, Girls Basketball, and Boys Cross Country—won section, WPIAL league, and State Championships and, as that Boys Lacrosse team did, rallied school spirit!

In Which Gary and Marty Have a Bewildering Day

Fundraising visits were a new adventure for me in my early years at WT. To build the Upper School and to complete the third phase of the North Hills Campus Master Plan, we had undertaken the first major capital campaign at WT since the 1980s. There were many relationships to rekindle, which usually provided me with great pleasure as people shared their stories, filling out the history and personality of what was becoming my beloved WT. I relished sharing our vision with people, and igniting their passion for the school.

Not every fundraising visit was immediately successful. One of my most memorable occurred when Marty Powell and I drove to a small town in Ohio to visit a prominent philanthropist with Pittsburgh ties. His son had been a WT Trustee at one time, and had passed away at a young age. There was some sense that this gentleman might consider a gift to WT in his son’s memory.

Marty and I arrived at a 1950s office building in the middle of a desolate rust belt town, and were called upstairs to an empty office. We milled around the room until our host burst through the door and hastily marched to his desk, where he sat down and grimaced at us. Marty sat in the chair immediately in front of the large desk and I grabbed the only chair left, which was off to the side.

Our prospect was clearly annoyed with us; he began to express his frustration in a gruff, profanity-laced lecture. It took a few minutes to follow the train of his loud accusations, but eventually I gathered that he had apparently given the school some advice about a personnel matter, and we had not honored it. And now we had the temerity to come to him and ask for money! I was baffled. Unable to make eye contact with Marty because of the awkward position of my seat, and with no knowledge of the situation, I sat silently on the side, unnoticed by the prospect while Marty took the brunt of his salty language. Within a few minutes, our host dismissed us unceremoniously.

We walked down the corridor dumfounded and humiliated. Why, I wondered, had no one told me about the past experience with this prospect? How could anyone have thought it was a good idea for us to visit him and ask for a gift?

Just then, an assistant stepped into the hallway and gently beckoned us into her office. She had overheard the conversation and was very apologetic. It seemed that our prospect had mistaken us for representatives of another local organization—one with whom he obviously had had an upsetting disagreement.

The drive back to Pittsburgh was quiet. After preparing for what we’d hoped would be a fruitful visit and being met with such hostility, we were both deflated. It would take us some time to look back on that bewildering experience and laugh—but eventually, we did.

And apparently it all got straightened out for our prospect, because he sent WT a generous gift later that year, and did so annually for many years to come!

Sixteen years is a long, long time, and it is also the blink of an eye. Heading Winchester Thurston has been a sacred trust. It has been an honor to tend the garden that was tilled by two incredible women, Miss Thurston and Miss Mitchell. Thanks to the efforts of my colleagues and the generosity of countless people, we have fulfilled the promise that I made in my first Thistletalk letter: to make the WT community proud. I want to thank you for your enthusiasm and your support. And for the many, many stories I will remember, tell, and cherish.