That was Charles' way of motivating Derek to win on his own; no freebies allowed. Derek would learn to savor victories when they came.
And now it's Derek who gets to grin, knowing that he has the upper hand on Charles in some things, such as tossing a baseball back and forth.
"Catch? He's too old for that," Derek said with a grin.
As Father's Day approaches, Derek and Charles stand out as a pair that has a fun, true and growing father-son relationship.
Charles has always poured himself into Derek's life. From teaching him character through the games they played to writing up contracts of expectations, Dad was there for Derek.
Jeter's Turn 2 Foundation, in particular, has bonded the two.
"He's always been there for support, advice, and he's always been there to bounce ideas off of," Derek said. "We're probably closer now than we were when I was growing up. We were close growing up, but especially through the foundation, we get an opportunity to work together as well. I talk to my parents every day, pretty much."
Charles, a social worker with a Master's of Social Work and doctorate degree from Western Michigan University, serves as vice president of his son's foundation. It's one of several pursuits that have brought the two closer. For the most part, though, Derek and his father enjoy what's free in life -- a good conversation. They don't have to go out or hire a catering service or dress in suits and ties.
"I don't know if it's necessarily doing anything, just spending time together," Derek said. "That's pretty much it. It's not like doing anything in particular. Talking is the thing we do the most."
Derek said that he and his father talk about anything and everything. Work, family, you name it. But with Father's Day just around the corner, there's one thing the two won't have to talk about: a Father's Day present. According to Derek, Dad isn't hard to shop for.
"He's pretty easy," Derek said, "because he tells you what he wants. He's not very difficult."
Caleb Breakey is an associate reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.