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Jeff Natale

Director of Admissions


  • Trinity College
  • Professional Baseball Player: Red Sox


Jeff spent most of his childhood playing both baseball and hockey competitively. Playing 2 sports at a high level led him to Trinity College in Hartford, CT where Jeff spent 4 years playing baseball and 3 years playing hockey. After college, Jeff was fortunate enough to be drafted by the Boston Red Sox in the 32nd round of the amateur play draft. Jeff played 5 years with the Boston Red Sox and 1 year with the New York Yankees before giving up his dream to make it to the big leagues. After playing baseball for such a long time, Jeff wanted to give back and help coach younger baseball players which led him to Milton Academy. At Milton Academy, Jeff was the “jack of all trades”—he primarily worked in the admission office but also lived in a boys dorm, advised and mentored 6 boys, coached hockey and baseball, and taught a health class. Jeff’s greatest passion is working with students, supporting them and helping them find their passions whether that be sports, performing arts, or academics. Currently at USPA, Jeff enjoys meeting and interviewing new families, and telling those families about all about USPA. He also loves to go to the beach, hike, run, and do crossfit. Jeff lives with his wife, his daughters, Kendall and Shay, and their 2 giant dogs, Tonka and Lulu.