Rainey was injured in a Sept. 3 scrimmage when was tackled on what appeared to be a normal play. He suffered a broken knee cap on the play, an artery was ruptured, and he was transported to Fair Oaks Hospital, then transferred to Inova Fairfax.
As the Tigers celebrated a season-opening win a week later, players began receiving word Rainey underwent surgery and had the lower part of his left amputated.
"His was big, physical, vibrant," Woodberry Forest coach Clint Alexander said. "To see him go down the way he did – it seemed like the most innocent tackle you've ever seen – it's really been tough because (his teammates) love him. It's really been hard."
Rainey remains hospitalized, and his distraught family is not ready to engage in interviews.
Communication from the family is being made in conjunction with the school and the Rainey family, Woodberry Forest director of communications Cathy Eberly said.
"The Rainey family is overwhelmed by the outpouring of interest and support they have received since Jacob was injured," the statement reads. "They are currently focusing all of their time and attention on his recovery and are not yet ready to speak with the press or to be interviewed. They expect to share their story at some point; in the meantime, they thank you sincerely for respecting their privacy."
To help fray the extensive medical costs, the Jacob Rainey Fund was established.
The injury, and the subsequent developments, rocked the Woodberry School, and the football program.
Rainey, a 6-foot-3, 215-pounder, was a big college prospect. He was receiving interest from a number of Atlantic Coast Conference schools, including in-state programs Virginia and Virginia Tech, as well as Duke and Vanderbilt.
Virginia coach Mike London reacted to the news of Rainey's injury during a press conference last week.
"Our thoughts and prayers go out to the whole Woodberry Forest football family, (and) to this young man's family, in particular," London said. "Wins and losses are important, but sometimes the reality of what's important, what's really important, are the young men and the family members, and the sons, and the things that we're responsible for."
Although the impact of the injury is greatest on Rainey and his family, the effects are being felt throughout the school, and the football program.
Woodberry Forest opened the season with a 16-13 win against Benedictine Prep on Sept. 9, but last weekend lost 28-21 at Blair Academy (Blairstown, N.J.). Each game, a Tigers player will wear Rainey's No. 9 in his honor.
"I think they really played hard for him," Alexander said. "They really played with a lot of passion and pride. This certainly reminded them of what's really important, and how you want to appreciate the people that are in your lives."
Counseling with family members, coaches, teachers and staff members at Woodberry is helping the players cope with the mental anguish of such an injury.
"We're doing a lot better now," Prosise said. "We've been pretty bummed, pretty low on morale. We hadn't been able to see him, and it's been really tough losing one of our guys, and one of the best guys you'll ever want to know.
"It was definitely tough seeing that. It changes you, and it changes the way you play. You start playing timid. I was just trying to be strong for my teammates. I wanted them to know I was going to play as hard as I can, do as much as I can, to keep morale up, and always be positive with everything that happened."
Donations to the Jacob Rainey Fund can be made to: Virginia National Bank, Jacob Rainey Fund, 102 East Main St., Orange, Va., 22960