Athletics has played a vital role in the lives of Andrew and Kim Gregory, who were high school sweethearts at Isle of Wight Academy. Andrew was a three-sport (football, basketball and baseball) star, being named the school’s athlete of the year in 1995, his senior year. Kim played basketball, softball and cheered, and was the school’s athlete of the year in 1996. Their son, Gavin, finished a four-year baseball career at Hampden-Sydney College earlier this year. Their daughter, Riley, played field hockey and softball in high school and is at James Madison University.
“Sports definitely we’re a huge part of our upbringing and what we enjoy doing,” Andrew said, specifically mentioning baseball and softball. “We really appreciated the impact (those sports have) had on our lives and our kids’ lives.”
Hoping to have an impact on others who want to enjoy sports at the college level, the Gregory Family Foundation, set up by Andrew and Kim in 2023, has made a $10,000 donation to the Virginia Peninsula Community College baseball team. Andrew estimates 80% of their donations to date have supported college athletics or youth sports.
“Those have been things that spoke to us, that we wanted to support, and we try to do things that will have a longer-term impact where we can,” Andrew said.
VPCC baseball coach Shane Harrison can use the money as he sees fit, but the two have discussed purchasing new uniforms, which are much needed.
“It’s huge,” Harrison said of the donation. “They came through very big for us.”
Oftentimes, items such as uniforms are on the list of needs for years but are pushed back because the team is paying for more immediate costs, i.e., umpires, equipment, travel, hotel and food, to name a few.
“We just wanted whatever other money they’re able to raise to be able to truly support the everyday needs,” Andrew said, adding covering the cost of a one-time item allows that to happen.
Andrew also hopes the donation brings attention to often overlooked programs.
“We really do want to help bring awareness to a program like VPCC is running,” he said.
Within the NCAA, Division I, II or III programs sometimes overlook community college players, missing out on great players and students.
“The programs that really bridge that divide are very important, especially now with kids wanting to do a two-year to save some money,” he said. “They play such a significant role so we’re excited to support it, but any awareness we can bring to that and just know that there are people who care about these types of programs.”
Andrew likes how community college programs also give players a chance to continue their playing career beyond high school. One of those players is Andrew and Kim’s nephew Jake Wells, who is in his first year with the Gators. The Gregorys have younger nieces and nephews so it might be a few more years before they can watch a family member play college sports.
“We’re excited to come watch some games,” Andrew said.
Andrew and Kim live in Suffolk and have been Hampton Roads residents all their lives. After a five-year stint as a teacher for the Newport News Public Schools System, he has been a financial adviser for more than 20 years.
“I did a complete career pivot into wealth management and have never looked back,” he said.
Kim retired after teaching for 25 years at Hampton Roads Academy. Their son is a project manager with Ryan Homes, and Riley is sophomore at JMU studying biology.
The Gregory Family Foundation doesn’t have a stated mission statement. But it’s the family’s way of giving back to sports and a community they have enjoyed being a part of for so many years.
“We decided to take some money and set it aside and create that foundation in order to be able to do some gifting from time to time,” Andrew said.
Harrison is very appreciative, and said the donation is a true reflection of the baseball community in the area.
“When somebody’s in need in the baseball community, if somebody can help out, they just do,” he said.
For more on VPCC athletics, go to www.vpccgators.com.

