After being drafted and signed by the Cubs and sent to Class-A Boise, he managed to steal 30 bases in his first 45 games, often swiping up to two and three a night. Gregg had seven stolen bases in his first four games alone with the team.
So how is it this 22-year-old mid-round pick's knack for driving opposing teams crazy on base went relatively unnoticed until only recently?
"I guess it's a matter of the system I was a part of in college," said Gregg, 32 of 40 in stolen base attempts with a .270 average through 55 games with the Hawks. "In college, we were more of a home run hitting team. Coach Tanner didn't let me run as much as I do here. Everyone knew I was fast, but he liked to get a guy on, bunt him over to second and drive him in with a double. I think the Cubs knew I was pretty fast. They saw me hit a double or two and saw how fast I could get from home to second."
Trey Forkerway, the first-year manager of the Hawks, was quick to pick up on Gregg's proficiency on the bases.
"One day," Forkerway said of how long it took him to notice Gregg's quickness. "That's all it took. A lot of times when players come to our organization, some things are said about them prior to their arrivals, such as what their game is. He happened to play in an exhibition game before we left Mesa, and one of the things we saw immediately was his speed and his ability."
Gregg admits, "Our manager here is more open to running. He pretty much lets you run as long as it's a good count and a good situation to run in. That's been the biggest thing for me. I've always been fast; I'm just now getting a chance to show it."
While in college, Gregg was redshirted his freshman year in 2002 and played in only 15 games the following season, primarily as a pinch-runner before becoming a starter his last two years in Columbia.
Gregg still has a semester of college left before he can graduate and obtain his degree. While at South Carolina, he majored in Business Management and minored in Criminal Justice.
"I was planning on finishing up this fall, but I was invited to instructional leagues so maybe next fall," said Gregg. "I have only five classes left. I also did a lot of marketing while I was in college."
Now with the Cubs, Gregg remains in close contact with Roving Outfield and Baserunning Instructor Vince Coleman. The former major leaguer was recently in town for the team's home series against Salem-Keizer and saw Gregg first-hand.
"He came in and showed me so many different things and various techniques and tendencies they have here," Gregg said. "He used his time in the big leagues as an example to teach me new things to look for and analyze on the bases every day. It's always great to have someone of that caliber helping us."
As for Gregg's hitting, he was a career .313 hitter with 24 extra base hits and 49 RBIs in college. He entered this month batting .307 with the Hawks before hitting a skid that dropped his average below .200 for August. He remains the team leader in hits with 60.
Without showing concern for the recent slide, Gregg is quick to point out that playing professional baseball leaves no time for staying in prolonged slumps.
"It seemed like I couldn't get a hit to save my life," Gregg said. "If I hit the ball hard, I'd hit it right to someone. Every pitch the pitcher made seemed to be perfect. I finally got a few hits one night and got myself going again. The whole thing about this game and this level of competition is being consistent. Baseball in general requires you to work your way out of those slumps. You have to keep trucking along.
"It's a marathon out here; not a sprint."
And so far, Davy Gregg is holding up quite well in that marathon.