Workshop with Bret Stephens ‘91: Overview and Insight

A guide on constructing Opinion Writing 

Photo by Adam Nestle

On Thursday, September 25, 2025, The Anvil team had the privilege of welcoming New York Times columnist and Middlesex alumnus Bret Stephens ‘91 back on campus. More than three decades after graduating from Middlesex, Mr. Stephens returned to campus to impart his insights on opinion writing to the Anvil staff and wider school community—an opportunity made possible by several of the Anvil’s new initiatives this year. From once sitting in the same English classes as ourselves to publishing globally acclaimed columns, Mr. Stephen’s journey naturally raises the question: what role did Middlesex play in shaping a writer of such influence? This article will cover the major takeaways, themes, and reflections from Mr. Stephen’s Workshop. 

A graduate of the Class of 1991, Mr. Stephens began his career as an assistant editor at Commentary Magazine in 1995-96 before joining The Wall Street Journal as an op-editor, eventually becoming an opinions columnist at The New York Times. Since then, Mr. Stephens has been named a Young Global Leader by the World Economic Forum, and received the Pulitzer Prize for Commentary. A critically acclaimed writer and reporter, Mr. Stephens’ insights carry particular significance at Middlesex, an institution that continues to kindle many students’ passion for writing.

With over 20 members of the Anvil staff and Middlesex community present, Mr. Stephens began his workshop by reflecting on his time at Middlesex. He founded The Circle—a student paper created to challenge The Anvil, which at the time didn’t nearly publish nor engage as much on campus. He reminisced on memories of his rebellious Middlesex career, including chaining his former Head of School’s bike to the Middlesex flagpole for an astounding cover image on The Circle. Memories like these, he explained, while not directly related to writing, shaped the independence and boldness he would later carry as a writer. 

These principles guided the themes of his workshop. Firstly, Mr. Stephens commented on how he confronts an increasingly polarized political climate. At the forefront of writing, Mr. Stephens believes that engaging with both liberal and conservative values is deeply important. To illustrate, he analogized progression in politics to a sailboat: progressive, democratic values serve as the sail that forwards policy and change while conservative values act at the keel that grounds us in stability and prevents tipping against radical tides. In addition, he emphasized the need for more mutual toleration in the journalistic sphere. As most journalists seek to comment on truth and ideals, it is important to confront conflicting views with constructive rather than dismissive feedback. Olena Khiznychenko ‘27 commented that she “respects his confidence in speaking out on more contentious and radical issues” in such a tumultuous political climate. 

Building on his message for open-minded dialogue, Mr. Stephens turned to the craft of opinion writing itself. He stated that all reasoned opinions, if well-researched and personally convicted, are worth writing about, especially when journalistic diversity in opinions is low. But more than that, he concluded that the best way to argue and ground these opinions is through concise but passionate language. Mr. Stephens himself wrote, “A wise editor once observed that the easiest decision a reader can make is to stop reading. This means that every sentence has to count in grabbing the reader’s attention, starting with the first.” In every opinion piece, it is important to ask yourself: Why does this matter? Why should I care? How do I make my reader care? Implicating value, in all writing, is the first and foremost priority for any writer in the journalistic space. 

Finally, he imparted that above all, the journey is hard, that if “you are finding writing easy, you’re doing it wrong.” The experience of writing is constantly changing and evolving as you consolidate your ideas. By no means should writing ever feel like a linear process, as all good writing is formed in the experience of struggling with the best ideas. Mr. Stephens concluded that, as writers, it is important to notice the independent worth of our ideas as moving pieces in a greater political climate. Without discourse, opinions, and writing, there cannot be true progression. Therefore, in every conflicted writer, there lies unbound value in evolving arguments and making change beyond our own opinions. 

Bryan Dong ‘27