This annual event provides DREAM alumni and a select group of DREAM Charter High School students the chance to network, grow their professional skills, and learn about exciting careers. DREAM secures dozens of professionals from a range of industries to serve as networking mentors for the evening, while organizations attend the event to engage DREAM alumni as prospective job candidates. The 2024 conference saw our highest number of Legends turn out to Yankee Stadium to meet with representatives from companies like Bank of America, Mount Sinai, and Blockboard, and to hear from keynote speaker Brian E. Smith, the Yankees' Senior Vice President of Corporate and Community Relations.

The Legends Mentoring Program connects 18-24-year-old Legends with mentors interested in leveraging their experience to coach young, prospective professionals. Mentees will be encouraged to develop self-advocacy skills, and wise decision-making practices, engage in identity exploration, and set goals that will prepare them for their careers and life-long success.

During this year-long program, participants are paired with external mentors considered experts in their field of interest to gain industry exposure and receive post-graduate transition support. Mentees will participate in bi-weekly communications with their mentor via phone, email, text, video call, or in-person; check-ins with their Mentoring Program coordinator; Mentor/Mentee Reveal Day; virtual professional development sessions; the annual Legends Career Conference; and the end of program celebration.