[5][6][7] Escalera was born in Santurce, San Juan, Puerto Rico where his baseball abilities were noted at an early age, and later moved to Bradenton, Florida[8] to enhance his training.

His father, Alfredo L. Escalera, MD, an internal medicine physician, met his mother, Nancy, a New York nurse of Hispanic descent while undergoing his medical training in the Long Island College Hospital.

Escalera's younger sister Gabriela has become one of her brother's closest advisors and is closely involved in his professional career.

Between the ages 9 and 12, Escalera participated in the internationally regarded IMG Academy Baseball Camp in Bradenton, Florida.

During Escalera's high school career he participated in over two hundred IMG scrimmage and spring games as well as several workouts, showcases, and tournaments across the United States and Puerto Rico.

Escalera mainly played for the IMG Royals but during the summer he joined the Puerto Rico Rookie Palomino Team (2010) and the Miami Bombers (2011).

[17] Just prior to the National Letter of Intent signing day, Escalera, determined not to join the FSU Seminoles and instead signed a Letter of Intent to attend Stetson University's business school where he was expected to be the starting centerfielder for the Stetson's Hatters Baseball Team.

The IMG Academy experience propelled Escalera's early talent into a solid professional skills player with good knowledge of the game.

[21] During his high school senior year Escalera was scouted by eighteen Major League Baseball (MLB) organizations.

He caught the attention of the professional southeast scouting staff who were regulars in Escalera's high school baseball games and workouts.

Mesa lobbied the Royals’ management team and later got support from Paul Gibson and Lonnie Goldberg, National Cross-Checker and Director of Scouting respectively.

"Combine Escalera's youth, glimpse of hitting talent, arm and speed and the Royals could have a true diamond in the rough" stated sports analyst Zach Mortimer.

[36] Escalera has shown a commitment with participating and supporting altruistic events organized to improve the quality of live of the homeless population as well as underprivileged kids.

During his recurrent outings to the Royals’ training camp in Surprise Arizona, Escalera has gotten involved in many humanitarian activities mostly related with assisting kids to get motivated to succeed in life.