Current students Lenora Winkelman ‘27 and Grace Mascio ‘26 are following in their family’s footsteps as they continue the long line of LT alumni dating back five generations. The legacy left before them by their ancestors has prepared them for their high school years to come. 

“I feel like this has paved the way for me because I always knew I was going to attend LT,” Mascio said. “I knew I was going to graduate from [LT] and follow what the rest of my family did.” 

Mascio is looking forward to meeting new people and excited for her swimming and water polo seasons to come over the next three years. Winkelman, her cousin, is a part of the marching band at LT, and is embracing the full high school experience. 

“I think it’s really cool to have [multiple] generations of people who all went to the same high school, in the exact same building,” Winkelman said.  

Winkelman’s current English teacher, Ann Dudek, has been at LT for 29 years and can only imagine the stories that have been shared across four generations, regarding the way things were and how they have evolved, she said. 

“I’m sure there are more students who have long family histories at LT, but it was great to hear the excitement in my student’s voice as she shared how she too was now following in the footsteps of her family,” Dudek said. “I was thinking about homecoming and the idea of always having a welcoming place to come back to. That should be our goal [as teachers,] to make LT a meaningful place and [positive] experience for all who walk through its halls.” 

Thousands of students have graduated from LT over the past 135 years, and since 1926, the Winkelman family legacy has been passed down from generation to generation. 

It all started with George Edward Winkelman, the great grandfather of Winkelman ‘27 and great great grandfather of Mascio. He was a member of the graduating class of 1926. Mascio and Winkelman will graduate from LT just about 100 years after their great grandfather and great great grandfather. 

During his time at LT, he played football, basketball, baseball and ran track and field, Lenora said. George married Nora Winkelman and they had three children who all attended LT. 

Two of their children, Ann Winkelman ‘50 and George David Winkelman ‘52, grew up in Western Springs and attended a private school first through eighth grade. During their time at LT, George ‘52 played baseball while Ann was captain of the bowling team. 

George ‘52 also attended junior college for two years at LT, which was located on the fourth floor of NC at the time. He later finished his college education at Valparaiso University. He married Lillian Winkelman who did not attend LT, but taught Spanish at LT from 1963-1969. They had two sons: Mark Winkelman ‘87, and Tom Winkelman ‘89, who is Lenora’s father. Both Mark and Tom attended Cossitt Elementary School and Park Junior High prior to highschool. 

Mascio’s great grandmother, Ann Winkelman ‘50, married Paul Jarabek and had five children. One of which, Ken Jarabek ‘75, (Mascio’s grandfather) played baseball and football at LT. Ken married Julie Jarabek and had two daughters: Stephanie Andersen ‘03 and Elizabeth Mascio ‘01, who is Mascio’s mother. 

“[Although my sister and I] were never at the same campus, I did have a locker near my cousin,” Elizabeth said. “I think it’s so cool that now Grace has a cousin at the same school, with the same lockers, same hallways, it’s wild.” 

During their time at LT, Andersen was involved in choir, cross country and soccer and Elizabeth was a part of the poms, tennis team, and was a part of choir as well. 

“It was pretty neat walking the halls of the school knowing that my parents, aunts and uncles, and grandparents did the same thing, in the same place,” Elizabeth said. “[They] had the same worries, hopes, embarrassments, struggles and giggles [as I did.] The shared experience feeling was palpable.” 

Gallery • 6 Photos

George Edward Winkelman class of 1926 poses for senior photo.