Gregory Highstrom was a four-year letter winner from 1998 to 2001 in swimming and captained the team his senior year. During his four years of swimming, Gregory was Conference Champion in the 100 yard backstroke three consecutive years starting his sophomore year. This same year he broke the conference 100 yard backstroke record with a time of 54.32. He then went on to hold the school record in the 100 yard backstroke with 53.71 seconds.

In WIAA postseason action, he was a four-time qualifier in the 100 yard backstroke.

Gregory also qualified in 12 other events over his career. He finished high school swimming by being a two-time State Champion in the 100 yard backstroke in 2000 and 2001.

Gregory attended and competed as a Division One swimmer at the University of

Wisconsin-Green Bay. He then enlisted in the U.S. Army and proudly served for 11 years as a Commander of Bravo Battery 2nd Battalion 4th Field Artillery Regiment, completing two tours in Iraq.