Special Jennings joined Montverde Academy in the late summer of 2020, and in that time she has rapidly catapulted the Eagles to an elite national program. In 2021-22, just her second season at the helm, Jennings led Montverde Academy to a 20-3 overall record and its first ever GEICO High School Nationals championship, which was also the first time in program history the Eagles qualified for the tournament. She led MVA to a 61-57 win over New Hope Academy to secure the team's first national championship.
En route to the historic season, Jennings coached individual players who were rewarded for their great play. Janiah Barker earned a host of awards for the Eagles under Jennings, including being named a McDonald's All-American, a Baden first team All-American, Jordan Brand Classic Selection, Women's Basketball Coaches Association All-American, second team All Naismith and a MaxPreps honorable mention. Another of Jennings' players, Fatima Diakhate was a Canadian Games Selection. In addition to Barker, three other players, including Diakhate, Jordana Codio and Fernanda Ovalle were McDonald's All-American nominees.
In her first year at MVA, Jennings coached the Eagles to their highest-ever ranking in the program's history at #1 on MaxPreps Top 25 list midway through the 2020-21 season. Jennings led the team to a 21-1 final record the same year, amassing such milestones as the program's first ever 100 point game and a 13-game win streak.
Her last position before MVA was as Associate Head Coach at The University of Illinois at Chicago, spending two years there from 2018-19 to 2019-2020. While the program was in a rebuilding stage during that time, they are poised for a successful season after the re-tooling of Special and her colleagues in the recent past.
Jennings is no stranger to Florida basketball. She spent the 2017-18 season as an Assistant Coach at Flagler College in Saint Augustine, Fla. She helped turn around the team's play during that time, earning a 16-6 record in the Peach Belt Conference in her final season. Even though it was only a brief spell at Flagler, Jennings left her mark in mentoring the 2018 Peach Belt Conference Defensive Player of the Year, Tabitha Odabe.
Before arriving at Flagler, Jennings honed her craft as Assistant Coach at Augusta University for three seasons. From 2014 to 2017, she played a critical role in scouting, player development, planning and conducting practices, and overall player development on and off the court. The Jaguars made it to the NCAA Division II "Sweet 16" in March 2016 and amassed 46 overall wins during Jennings' tenure.
Prior to her time at Augusta, Jennings got her start as an administrative assistant for the women's basketball program at Wright State for the 2013-14 season. She assisted in many aspects of the program, most notably serving to ensure players maintained academic excellence. Wright State earned their first Horizon League Championship and first NCAA Tournament appearance with her on the bench in 2014.
Jennings stood out as a player, starting 115 consecutive games at Xavier University. She is currently tied for fourth in all-time assists for the Musketeers with 515. She also still holds the fifth-place spot in Xavier's all-time free throw percentage at .773. Jennings led the Musketeers to an NCAA "Elite 8" appearance in 2010, four Atlantic 10 Conference Tournament titles, and three other NCAA Tournament appearances.
Jennings then went on to spend 2011-13 as a professional player in Finland.
