8. Mariah Carey

Derek Jeter got his fair share of reps out of the leadoff spot throughout his career. Looking at his side career in dating, it is safe to say that Mariah Carey served as the catalyst.

Serving as the first celebrity girlfriend for the rising star, the famous singer/songwriter gave him experience on just how to land the biggest fish in the sea.

Let’s just say her leadoff prowess could earn her a spot on the 2016 New York Yankees. This list being present today is a long-term result of their relationship.

 Next: Girlfriend No. 7