Finley, pitching for Class A Short-Season Staten Island, and his family used to joke that he may play in the pinstripes one day. But it wasn't for the usual reasons someone would think, because Finley grew up rooting against the Yankees.
David Finley, Drew's father, worked for the Red Sox for 13 seasons, so the entire Finley household grew up fans of the Yanks' archrival. David also had a short-lived Minor League career in Oakland's system, and he now works for the Dodgers as the vice president of amateur and international scouting. But when the 2015 Draft rolled around, it was time to get down to business.
Finley hoped to be drafted by a reputable organization -- a place his father had no ties to -- and he couldn't have dreamed of a better club.
"The whole Red Sox thing was in my persona, but I wanted to be drafted by the Yankees," he said. "[My family] always joked around when my dad was with the Red Sox saying, 'Oh, Drew's going to be a Yankee,' so it was cool that it came true."
The Southern California native was selected by the Yankees in the third round in 2015 right after graduating high school. Finley originally committed to playing at USC, but he opted to get a head start on his professional career instead, and he hasn't looked back.
However, the transition wasn't a piece of cake. Finley was forced to get used to a new level of play and a new list of responsibilities right from the get-go. While it was fun at first -- and it still is, for the most part -- the constant stream of games and practices made Finley realize what he was in for, not just on the diamond, but in life.
"I was excited that I got to play baseball every day, but then you get to the grind part of it, and it's all about mentality and how you approach each and every day," Finley said. "It's not like high school, where you know you're the top dog and people right away respect you. You have to make your mark, show your personality and go in and do your work and be humble."
Finley is confident he made the right decision. When he looked at all the pros and cons of forgoing college, he didn't find many cons, and his decision was rather easy. But that doesn't mean Finley completely turned his back on USC or receiving a college education.
Finley can often be found sporting USC apparel, and although he took a one-year hiatus from school, he is planning on enrolling in a few classes through a community college this offseason.
The No. 15 prospect for the Yanks according to MLBPipeline.com, Finley is steadily improving. However, he admits there have been a few bumps in the road. Finley is 0-3 with a 4.28 ERA through 27 1/3 innings this season. He thinks things are starting to smooth out now, and he is eager to see what the rest of the season holds.
"I want to look at myself at the end of the year and say that each day I worked hard and got better, and anything that put me two steps back, hopefully I jumped five steps forward," Finley said.
So while Finley may have grown up a Red Sox fan, he's focused on what lies ahead of him in the Yankees' system.
"I've always said it, but I was blessed to be a kid in the Red Sox's clubhouse, and now I'm honored to be a Yankee," he said. "The past is the past -- I'm a Yankee now, and hopefully I spend the rest of my career in the pinstripes."