Walking through the pair of double doors in the field house entrance, so heavy you need to use two hands, the same feeling every year on the first Saturday of the spring season. The sound of tennis balls hit with spin and the colors of eight different schools’ uniforms blurring into a kaleidoscopic cluster bring it all back. You head to the Hospitality Suite, already in uniform, put your bag down, grab some tennis balls, find a player from your team, and go hit in the most inconvenient spots, with all seven courts filled with four people each at 7 in the morning. When KO’s varsity Head Coach Andy Krugman ’86 finally rounds up the 40 players and coaches to the first court for introductions, you can’t help but give a little smile. The KITT has finally arrived.
The KITT – Kingswood Invitational Tennis Tournament) – is our annual boys tennis pre-season tournament, held onthe first Saturday after spring break. It includes eight different teams: Deerfield, Lawrenceville, Westminster, Groton, Hall, Hotchkiss, Choate, and, of course, KO. The KITT however, isn’t just an annual tournament we host every year; it’s an engraved piece of history that stretches way back in the 20th century and runs to this day, being a tradition everyone looks forward to.
The KITT was started by Chuck Glassmeyer in 1973, the Varsity head coach of the team at the time. “He wanted to have an invitational tennis tournament,” Coach Krugman said, “and so he just invited a bunch of schools and sort of started it from nothing.” And, before you knew it, Chuck’s little idea turned into an annual KO event that all eight participating schools look forward to,going on for the last 51 years, including the two years where it did not take place due to COVID.
However, the current eight teams weren’t the original eight; in fact, it was originally four. “There was a stretch of time when Hopkins came to this tournament,” Coach Krugman said. “There was this stretch of years when Taft came to this tournament. Milton came one year ago.” But among the eight original schools, the one that remains to this day is Lawrenceville, only invited in the first place being that one of Chuck’s good friends was the coach at there.
Coach Krugman had a year’s worth of play in the tournament. In his senior year — 1986 – he played two doubles, ultimately losing in the semifinals. However, he came back to KO to become the head coach of the team in 1992. “I had no idea at the time that six years later,” he said, “I’d be in charge of the tournament; it’s crazy.” From then on, he pretty much inherited the tournament from Coach Glassmeyer, still running it to this day.
Coach Krugman also talks about how even though we have been inviting some of the best teams in New England, and KO usually being the only day school in the tournament, we still have done very wellin the past. “Kingswood won it from ’74 to ’80,” Coach Krugman said. “They had a streak where they won it all those years.” Ultimately, apart from those seven years, we have done it seven other times.
This tournament is a very special tournament, not just to KO, but to all the other teams participating. Deerfield junior Gunter Weldon says that winning the tournament as a team, and the No. 1 singles final as well as No. 1 doubles, was a keystone in his career. “Winning last year was like the best memory I’ve had playing tennis at Deerfield,” he said. “It was pretty special to me. And then coming back, I was very excited.” Thisgoes to show how much this tournament really means for not just KO, but also for the other teams.
Even though this tournament has been going on for 51 years, it still has relevance to be played every year, and the legacy of the tournament has a huge impact on the players as well. Gunter also talked about how one of his friend’s dad won the tournament when he went to Deerfield. “His Deerfield team won the KO tournament when he went to Deerfield,” Gunter explained, “so when he saw that we won, it was kind of a cool connection that this tradition is still going.” And this goes to show the everlasting connection that people have to this tournament, even after graduating.
This tournament, over the years, has been dedicated to one player in particular, who reshaped KO tennis entirely. Tim Burtman ’78, a KO alum and former player, always displayed the utmost class. He brought his team up, showed amazing sportsmanship, and was a great person. He unfortunately passed away from cancer soon after his graduation. However, to this day, we honor Burtman before every home match, when the captains introduce him and his legacy.
The KITT is not just about history, however; it is about the experience that players go through every single year. Compared to a normal high school tennis match, or even a USTA – United States Tennis Association – match, the environment is completely different. “You’re there with your whole team,” Gunter said. “It’s energetic and exciting.” Unlike individual tournaments, where players often compete alone, the KITT creates a team atmosphere where players constantly cheer each other on between matches.
The team atmosphere is something that stands out to KO players as well. Senior Captain Pratt Blair describes the tournament in one word: community. Teammates spend the entire day supporting one another, watching matches, and building connections that go beyond just the sport itself.
Countless, smaller traditions that make the tournament memorable. “We have to leave campus at 6:15 in the van,” Gunter said, “so those two days are the only two days of our season where we are there that early. The one little memory I have that brings me back to the KO tournament, and we always get Dunkin on the way there, which makes it a fun little tradition.” Even simple things like stopping on the way for food contribute to the KITT experience.
In the end, the KITT is more than just a tournament. It is a tradition that has been built over decades, connecting players from different schools, different generations, and different backgrounds. Whether it’s a senior playing their final KITT in the final, a freshman’s first KITT in the first round, or an alum looking back on their memories, the tournament continues to have an everlasting impact.
As players walk through those same heavy double doors each spring, hearing the same sounds and seeing the same courts filled with competition, one thing remains the same: the KITT continues to be more than a tournament. It’s a legacy.

