Overbey, drafted in the tenth round last month, is brutally honest with the situation and what it could turn out to be.
"I'm 18, and the most (money) I've had in my wallet is a couple of hundred dollars ever. When you sit there and there's a lot of money in your face, it changes everything," Jake said. "Just the thought process kind of shook me. You can think all you want to up until the draft, but once you get drafted, it just changes."
Overbey, an infielder that plays shortstop or second base, is playing this summer for Dulin's Dodgers out of Memphis, Tenn. He's trying not to get caught up in the proceedings too much as far as the Phillies go. He's just enjoying playing baseball.
He said he was forewarned things might be methodical and even slow.
"I was told before the draft that it's a long process," he said. "So I was kind of expecting it. It has been a long process, but I'm not upset about it. I'm just letting it play out. I've got one more month."
But Overbey said he doesn't feel it will take that long for him to have a resolution.
"I really have no idea, but I don't think it will," he said of waiting until the Aug. 15 deadline.
Preston, drafted last summer by the Rays in round 42, is in summer school at Ole Miss currently. Jake said he welcomes his advice and that of all his family as well. But Jake said ultimately he will decide what he's going to do.
"Everything is my decision, but I talk to them and they give me their input and opinion," he said. "But it basically comes down to my decision."
Preston being on the team at Ole Miss is a strong factor in the Rebels' favor.
Overbey said he talks to the Phillies fairly often. He talks to Ole Miss head coach Mike Bianco and assistant coach Carl Lafferty quite a bit as well.
There has been some progress between him and the Phillies.
"I would say we're starting to get on the same page of where we both are," Overbey said. "That doesn't mean we've got an agreement. We're just trying to make sure we're on the same page as to what I want and what they want to give me."
Ole Miss signee outfielder/RHP Michael Reed, a fifth-round pick of the Brewers in June, has expressed interest all along in signing with the pros. He hasn't yet but basically still plans to do so.
Overbey becomes the next highest drafted incoming Rebel that is weighing his options. The 6-foot-2, 190-pound University School of Jackson (Tenn.) product said he has come to terms with being selected in the tenth round.
"I was actually real surprised," said the two-time Mr. Football in Tennessee at quarterback in his school's classification. "I've just tried not to get my hopes up about the whole draft situation. It seems like you hear so many stories about somebody wanting to go this way or that way, and they end up being upset. The whole thing is I'm just trying not to expect anything from it. I was surprised (at being picked in the tenth round), but I was real happy."
There are many important factors involved. He's dreamed of playing professional baseball. He's always thought he would play for the Ole Miss Rebels. He has two good options.
"That's still the way I'm thinking about it," Overbey said. "Right now I'm still leaning more toward Ole Miss. They (Phillies) have to give me enough for me to give up Ole Miss. Right now it's Ole Miss until they offer me that much. And right now I have no idea what that much would be."
"Either way is a win-win," he concluded.
For Ole Miss, however, only if Overbey chooses college is that the case.