Staff

Jack Gilmore

Director of Football Operations

Jack is a native of Mobile, Alabama. He attended St. Paul's and then graduated from The University of Alabama with a degree in Kinesiology. Jack was a preferred walk-on for the Crimson Tide Football Team as well as a Recruiting Specialist from 2012-2016. During this tenure, Jack was a part of two National Championships and three Southeastern Conference Championships. 

 

Following his time at The University of Alabama, in 2017, Jack served as a Graduating Assistant at the University of North Alabama, assisting with the defense, and coaching the safeties. In 2018, Jack spent Training Camp with the Buffalo Bills assisting the Operations and Personnel departments.

 

Following the internship, before returning home to the Senior Bowl, where he served as a Scouting Assistant under first-year Executive Director, Jim Nagy.

Following the 2019 Senior Bowl, Jack accepted a position with the Oakland Raiders as the team's College Scouting Coordinator. During his tenure with the Raiders, Jack assisted all efforts pertaining to College Scouting and NFL Draft preparation. He worked under two different General Managers and was a part of the transition from Oakland to Las Vegas.

 

In 2023, Jack returned to the Senior Bowl as the Director of Football Operations. As the Director of Football Operations, Jack assists with player evaluations, manages the player onboarding process and oversees the following support staff during game week: coaching, equipment, trainers, video, and officials. Jack is the son of Shannon and Bo Gilmore and has one older brothers, Joe, who is the Head Coach at St. Luke's Episcopal School.

 

Elizabeth DuPree

Director of Corporate Sponsorships

Elizabeth DuPree joined the Senior Bowl team in June of 2019 after 18 years leading sales account management and operational teams.  Responsible for recruitment and renewal of corporate sponsors and Quarterback Club membership, Elizabeth will partner closely with local and national sponsors to provide meaningful value to businesses and uphold the excellence, tradition and prestige that the Senior Bowl brand represents.  Born and raised in Mobile, AL, Elizabeth is an enthusiastic Crimson Tide football fan and loves spending time with her husband and 2 children on the water. Elizabeth holds a Bachelor’s degree in History &  Political Science from the University of Alabama.

 

Sylvester Croom

Senior Vice President of Operations

Sylvester Croom joined the Reese's Senior Bowl in May of 2018 as an honorary member of the staff. He spent more than 25 years as an assistant coach in the National Football League, with nine different clubs. From 2004-2008 he was the head coach at Mississippi State University, where he was the first African American head coach in the history of the Southeastern Conference. He was named the SEC Coach of the Year in 2007 after leading the Bulldogs to eight wins, including a victory in the Liberty Bowl. Croom attended the University of Alabama, where he played for legendary coach Paul 'Bear' Bryant and later started his coaching career at his alma mater as an assistant under Bryant and Ray Perkins.

 

Molly Middleton

Media & Community Relations Manager

After working for the Senior Bowl as a media relations intern for three years, Molly Middleton joined the full time staff as the media relations coordinator in September of 2021. She graduated from The University of Alabama in 2020 with a bachelor's degree in public relations and a minor in sport communications, where she was a student recruiter and communications assistant for Alabama Athletics. Molly specialized in basketball, football, golf, rowing, and soccer during her time working for the Crimson Tide.

 

Molly is the first point of contact for all year-round media inquiries, serving as the primary liaison between the Senior Bowl and national and local media. She is responsible for and oversees all game-week communication, including Media Day and interview schedules for players and coaches. She also manages the executive director's interview schedule and assists with the planning, implementation, and execution of all Senior Bowl events throughout the year, including, but not limited to, the Quarter Back Club event, Senior Bowl Committee parties, the Charities Celebrity Golf Classic, Turkey Bowl, and the Senior Bowl Hall of Fame.  

 

Johnny Williams

Creative Content Coordinator

Johnny Williams was added as creative content coordinator.  “Johnny Williams brings a unique football background as a Power Five player (at Duke University) to the creative side of our team.  He not only understands the game, but he is also skilled at bringing it to life through his artistic talents.”