However, none of those gloves will ever mean as much to Drew as the one his dad came home with one day when he was just a young boy.
"We didn't have money growing up, so when something came in like a brand new glove, it was really something," said Drew, who was born in tiny Hahira, Ga. "One day, dad was at the dumpster and just came home with a glove for me. He just found it."
Drew's two older brothers, J.D. and Tim, both of whom, like Stephen, were first-round Draft picks, already had gloves courtesy of Lance Burns, who worked at the Valdosta (Ga.) Boys and Girls Club.
"He helped us out," Drew said. "Lance knew who we were. He saw the talent in all three of us. They had some stuff from Lance that had been handed down. Growing up having those hand-me-downs from the Boys and Girls Clubs meant a lot."
That glove that Drew got from his dad is long gone now and he's not sure who manufactured it, but he remembers the crisscross webbing that it had. It's the same one that all his current gloves from Rawlings have, a basket weave webbing.
Drew used the Rawlings model while starring at Florida State University and continued using it during his rapid rise through the D-backs' farm system.
The basket weave model glove is more popular with pitchers these days than position players. In fact, it's believed that Drew and Yankees star Derek Jeter are the only two big league infielders using it.
The model is named after Jeter -- PRODJ2.
"It just feels comfortable," Drew said. "I've tried to go other model gloves and I can't do it. It brings back memories, using that kind of webbing, it reminds me of what that glove meant to me at the time. That's why I still use it."
The memories that the webbing brings back include Drew playing baseball outside with J.D., Tim and kids from the Boys and Girls Club or the local church group.
"We just loved to play the game," Drew said. "We were always outside playing. Kids today have Nintendo games and stuff. We didn't have that. Every day, my mom would send us out to play. The only thing she worried about was us breaking windows, which we did about four of five of them."
Drew is given several gloves each season, and while one may turn into a gamer or a backup, the others definitely do not go to waste.
"What I do with my gloves now is I give them to kids that are less fortunate," Drew said. "I give them either to someone back at home, or my brother-in-law coaches a high school team in Dallas, so I might give it to someone there.
"I know what dad did for me getting that glove. I know it's crazy that he found it in a dumpster, but at the same time, it was a brand new glove, so it meant a lot."
Steve Gilbert is a reporter for MLB.com. Read his blog, Inside the D-backs, and follow him on Twitter @SteveGilbertMLB. This story was not subject to the approval of Major League Baseball or its clubs.