Gilman’s Greatest Alumni

Of the many questions frequently circulating the Gilman community, including “Where did Mr. Smyth really learn to unicycle?,""How many deans will be added before the school has more deans than students?,” and “What really happens in Mr. Malkus’ comedy elective?,” one query reigns above the rest: who is Gilman’s greatest alumni? In almost 130 years of history, Gilman has had its plethora of successful businessmen, politicians, artists, and athletes. What defines the greatest alumni, and which alumni is truly the greatest? To answer these questions, The News went profession by profession in search of the ultimate Gilman man. Beginning with politicians, we then moved to athletics, authors, artists, educators, war heroes, and businessmen in search of prominent alumni.  

Beginning in the area of policy making, Gilman has its fair share of big-time politicians. Locally, this list includes Kevin Kamenetz ‘75, who served as the 12th Baltimore County Executive from 2010 to 2018 and Gerry Brewster ‘75, who served on the Baltimore County House of Delegates and Judiciary Committee from 1991 to 1994. At the state level, Malcolm Ruff ‘02 has been in the Maryland House of Delegates, from District 41, since 2023, and he is currently running for the West Baltimore State Senate seat; Governor Robert Ehrlich ‘75 served as the 60th Governor of Maryland from 2003 to 2007; and taking a trip down south, Gilman alumnus Governor Fife Symington ‘63 served as the 19th Governor of Arizona from 1991 to 1997. While in high school, Symington is famed to have rescued inebriated and future-president Bill Clinton from drowning while visiting Hyannis Port, Massachusetts. Finally, federally, John Sarbanes ‘80 served in the House of Representatives for Maryland’s third congressional district from 2007 to 2025; Benson Legg ‘66, nominated by President George H. W. Bush in 1991, served on the United States District Court for the District of Maryland until 2013; and although Maryland Senator Chris Van Hollen did not attend Gilman, his father, Christopher Van Hollen Sr. ‘41 did, and interestingly, served as the United States Ambassador to Sri Lanka and the Maldives from 1972 to 1976 under Nixon and Ford.     

Moving on to everybody’s favorite category, professional athletics, Gilman has represented the genre well with both players and other professions in the field. Lecky Haller ‘75 is a two-time Olympian in whitewater canoeing, placing fourth in the Barcelona games in 1992 and winning medals on four different occasions at the ICF Canoe Slalom World Championships, including a gold and two silvers. In the MLB, Gavin Sheets ‘14 currently plays for the San Diego Padres, John P. Angelos ‘85 served as the Chairman and CEO of the Orioles from 2020 to 2024, and Mark Shapiro ‘85 served as the General Manager and President of the Cleveland Indians before moving to the Toronto Blue Jays, where he now serves as President and CEO. Lacrosse wise, Ryan Boyle ‘00 played for the Philadelphia Barrage and the Boston Cannons in the Major Lacrosse League from 2004 to 2014, in which he was named the 2004 Rookie of the Year. He also was a three time member of Team USA in the World Lacrosse Championships. Currently, Marcus Holman ‘09 plays for the Boston Cannons in the PLL, in which he is an 11 time All Star and was the league-wide leading scorer in the 2019 season. Likewise, Piper Bond ‘18 has played for the Utah Archers since 2023. In the basketball world, Colin Pine ‘92 was the translator for first-overall draft pick Yao Ming on the Houston Rockets. Finally, Frank DeFord ‘57, although not associated with a single sport, wrote for Sports Illustrated from 1962 to 2017; he is a member of the National Sportscasters and Sportswriters Association Hall of Fame, was a six times National Sportswriter of the Year, and was named as the Magazine Writer of the Year by the Washington Journal Review twice.  

There have also been a fair share of Hounds in the NFL, many a product of the Poggi era. Of these include Victor Abiamiri ‘02, a second round draft pick that played five seasons with the Eagles from 2007 to 2011; Brandon Copeland ‘09, who played for ten seasons from 2013 to 2022, including two stints with the Ravens; Darius Jennings ‘11, who played for a variety of teams from 2015 to 2021; Cyrus Jones ‘12, a second round draft pick who played from 2016 to 2019; Micah Kiser ‘13, a fifth round draft pick who played from 2018 to 2022; and Thomas Booker ‘18, who was drafted in the fifth round and currently plays for the Raiders. After retiring, Abiamiri, Copeland, and Jennings have all become business leaders. 

We also have an abundance of successful artists. With the pen, famed author and historian Walter Lord ‘35 has received international praise for his 1955 telling of the Titanic: A Night to Remember. Timothy Parker ‘78 is famed for creating the ‘Universal Crossword’ that was managed by the Universal Press Syndicate and sent to newspapers worldwide. Parker currently holds the Guinness World Record for “World’s Most Syndicated Puzzle Compiler.” Acting wise, Nicholas David Pryor ‘53 famously played roles as a conflicting father in movies and TV shows, notably in Risky Business (1983) and Beverly Hills (1994-1997). Remak Ramsey ‘54 was another famous stage and television actor, known for Julie and Julia (2009), The Stepford Wives (1975), and Addicted to Love (1997). 

In the realm of production and composition, documentarian Allen Moore ‘70 produced numerous works that received high praise, including Wild by Law (1992), which earned Academy Award nomination; Baseball (1995), which earned a Primetime Emmy Award nomination; and Monkey Trial (2002), which earned a George Foster Peabody Award. Judah Adashi ‘94 is a famed pianist and composer at the Peabody Institute, and Derrick Wang ‘02, another composer, received international acclaim as the composer for “Scalia/Ginsburg,” the opera about United States Supreme Court Justices Antonin Scalia and Ruth Bader Ginsburg. Finally, in a slightly niche occupation, Bradley King ‘02 is a famed theatrical lighting designer, known for his contributions to Natasha, Pierre & the Great Comet of 1812 and Hadestown, for both of which he won the Tony Award for Best Lighting in a Musical in 2017 and 2019, respectively.  

Gilman alumni also lead in the education sector. Of course, Redmond C.S. Finney ‘47, an All-American football and lacrosse player and Princeton and Navy veteran of the Korean War, served as Gilman’s headmaster from 1968 to 1991. Mr. Finney is known for his work at creating an integrated Gilman and for preparing boys to be first class citizens. Another headmaster, Andrew Matire ‘89, served as the Head of School at Calvert and the Tatnall School in Delaware; he now serves as the Head of School at Landon. Finally, Charlie Cahn ‘88 has served as the Head of School at Suffield Academy in Suffield, Connecticut since 2004. 

There have also been a few Hounds that have stood out while bravely protecting our country. Ensign C. Markland Kelley Jr., who attended Gilman in the 1930s, was a top lacrosse goalie that enlisted in the Navy during WWII and was killed in action at the Battle of Midway. After his death, his father established the Ensign C. Markland Kelley Jr. Memorial Foundation to support community, cultural, educational, and youth programs. Likewise, the Ensign C. Markland Kelley Jr. High School Lacrosse Award is given to the top high school lacrosse player in Maryland each year. Kelley actually completed his high school education at McDonogh after beginning at Gilman, but his bravery is worth noting. Another veteran is John W. Nicholson Jr. ‘75, who served as a four star general, commanding American troops in Afghanistan. 

Finally, there have obviously been a surplus of alumni that have found great success in the business world. Of these include William P. Carey, founder of the W.P. Carey & Co. real estate financing firm and educational philanthropist, whose efforts included establishing the Carey Business School at Johns Hopkins. Carey left Gilman to attend the Pomfret School in Connecticut, but his impact on our school is evident by the name of our main building. Other business stars include hedge-fund manager turned Gilman and college football coach, Biff Poggi ‘79; Founding Dean and CEO of the Kaiser Permanente Bernard J. Tyson School of Medicine in Pasadena, California, Mark Schuster ‘77; founder of Charm City Run, Joshua H. Levinson ‘89; and corporate attorney and President and CEO of the Baltimore Grand Prix, Jay Davidson ‘85.

Woah. As you can see, there are quite a lot of options to choose from. So with all of this being said, who is Gilman’s greatest alumni? Is it famed historian Walter Lord? Blue Jays CEO and President Mark Shapiro? Olympic canoer Lecky Haller? Sports Illustrated Writer Frank DeFord? Or maybe even war hero Ensign C. Markland Kelley? To me, there is only one answer: Head of School Mr. Redmond C.S. Finney. In my opinion, the greatest Gilman alumni is the man that has given the most back to the school. Mr. Finney raised generations of boys to be first class citizens, to make the world a better place by picking up our political, social, economic, cultural, and global trash rather than easily walking by it. He influenced thousands of Gilman men. But who am I to pick! With the full list of Gilman greats at your disposal, who do you think is Gilman’s greatest alumni? Take a look at the essay contest to see some current students’ opinions.