He didn't make a big deal about the lack of transportation and actually grew to enjoy the walk. What he didn't realize, however, was that someone was watching.
For three consecutive days earlier this week, veteran right-hander Adam Wainwright passed Sherriff on his way to the park. Each time, Sherriff was further away than the last. Wainwright was too curious to leave the observation alone.
He approached Sherriff on Wednesday and, after learning that Sherriff did not have a vehicle, offered him a bike or a car. Sherriff politely declined and went about his day. Then, shortly after walking home that afternoon, he received a call from a member of the Cardinals' equipment staff.
There was a Nissan Altima at the complex with his name on it, Sherriff was told. Wainwright had taken care of the rental car cost.
"I started crying because no one had done anything like that for me," Sherriff said. "It was awesome."
For Wainwright, it was a pay-it-forward moment.
"That's the kind of thing that happened to me when I was younger," Wainwright said. "I remember I wore a couple of tired collared shirts a couple days in a row to the field, and Mark Mulder bought me a whole box of collared shirts. Many, many things like that happened to me, so you just kind of pass that stuff on."
Seeking to find a way to properly thank Wainwright for the gesture, Sheriff did some cyber sleuthing. Wainwright's Twitter bio lists some of his favorite things, and Sherriff used that background knowledge to put together a gift, which he left in Wainwright's locker on Thursday.
There, Wainwright found a gift card to Chick-Fil-A, a jug of sweet tea and a bottle of A-1 Sauce. Along with the items was an unscuffed baseball on which Sherriff had written his name and placed a bow. There was also a thank you note.
"That's the best thank you gift I have ever had," Wainwright said. "It was funny. He wrote a very nice note to me. He wrote, 'I accidentally bought steak sauce instead of barbecue sauce.'"
Wainwright laughed, then added: "It made it even better, I think."