Crosby grew up playing soccer and Cross country. He attended New Mexico Military Institute from 2010 until his acceptance to the Naval Academy in 2015. His first time sailing was during plebe summer at USNA, where he decided he wanted to be a part of the Offshore Sailing Team. He started as a foredeck aboard the Colgate 26's, and continued as a mast/bowman on the Farr 40s Patriot and Ranger, the Swan 56 Apollo, and the Navy 44's NA 22 Integrity and NA 23 Defiance, his current boat assignment. He has competed in many regattas, Most notably the 2016 NYYC Annual Regatta, the 2016 and 2017 Martha's Vineyard Race weeks, and the 2017 Marblehead to Halifax race. Majoring in astronautical engineering.