Outside the Lines Mentorship Program was built on the belief that real baseball development happens long before a player steps onto the field — and long after the game ends. Our program combines two powerful perspectives: the on-field experience of a former professional baseball player, and the real-life insight of a parent who has lived the entire youth baseball journey.

Jacob McCaskey
I’ve spent over 20 years in baseball — from youth ball, to earning All-American honors at California University of Pennsylvania, to finishing my college career at Gardner-Webb University, and eventually pitching professionally in the Frontier League and Pioneer League. Along the way, I learned that players and families often feel lost navigating confidence, adversity, development, and the pressures of the sport.
I created Outside the Lines to become the mentor I wish I had growing up — someone who understands the game on a deep level and can guide athletes through every stage of their development, both on and off the field.

Jim McCaskey
As a baseball parent, Jim lived every inning, practice, road trip, hard conversation, and emotional high and low throughout my career. He understands firsthand the confusion, pressure, and responsibility parents feel when trying to support their athlete. His role in the program is to guide parents — helping them navigate communication, expectations, emotional moments, and the long-term baseball journey.
Together, we provide full-circle mentorship: I work directly with the player, and Jim mentors the parent.

Our mission is simple — to help players grow as athletes, develop as people, and strengthen the connection between parent and player throughout the entire baseball experience.