A year ago, he daydreamed at his computer as he scrolled through the names of the 2007 First-Year Player Draft and mentally included his own.
Fast-forward to 2008, and Skipworth being taken in the first group is no fantasy. And he very well could be the first catcher selected.
"It's actually pretty surreal," Skipworth said. "I was thinking that I want to be that kid, but now that I'm in that situation, it is kind of like a dream that I live in every day."
Skipworth, 18, is a left-handed-hitting senior catcher at Patriot High School in Riverside, Calif., and has already been compared to the Twins' Joe Mauer.
At first glance the comparisons are fair. Both play the demanding catching position and hit from the left side. Mauer stands 6-foot-5 and tips the scale at 220 pounds, while Skipworth is an inch shorter and will likely fill out to a similar weight.
Mauer also lived up to his projection and was taken in the first round by Minnesota in 2001 with the top pick in the Draft. But he currently has one distinct edge over the potential prospect: Mauer is an All-Star in the Major Leagues while Skipworth is competing for the California Interscholastic Federation title.
Those around him, though, see nothing but upside, and it's not all about playing baseball.
"He is definitely a first-round Draft pick by all means," Patriot head coach Tim Kleveno said. "He is very mature for his age and he's a great leader, a well-rounded student and person."
And that assessment is not just the glowing report from a coach.
"He's intelligent, he can hit and he's a good kid -- it's nice to see guys like that make it," one scout said. "A lot of teams will shy away from taking a catcher that high, but I wouldn't. He's projected in the first half and I've heard as high as top 10."
Skipworth is expected to be more of an offensive threat but also shows plus arm strength. He hit .566 with 11 doubles, 13 home runs and 47 RBIs and posted a 1.844 OPS this season.
A varsity starter since his freshman year, Skipworth began hitting the national radar when he had a team-high 16 RBIs as the U.S. youth national team won the gold medal at the Pan American Championships in Venezuela following his sophomore season.
Skipworth then hit .422 with eight home runs and 45 RBIs in his junior year and collected three RBIs at last summer's AFLAC All-America game.
This season he showed remarkable consistency when he rang up a string of 18 consecutive base hits to break Shane Mack's California state record from 1981. The streak established another state record as he reached base safely in 25 consecutive plate appearances.
Kleveno said he was unaware of the streak until a scout called to ask. Seeing Skipworth get another hit was no surprise, as he was carrying the team to its 25-2 season record, Kleveno said.
But what has impressed his coach more is Skipworth's desire to improve, and added the attention he's been getting while being thrown into the spotlight has not caused his player to press but to get better.
"He works extremely hard, and he takes pride that he's become a more disciplined hitter," Kleveno said. "He was kind of a free swinger and didn't have too much discipline. Being sort of well-known has forced him to become more disciplined, not swing at bad pitches because he doesn't see too many good pitches, so he has to make them count."
For Skipworth, the work has been less about improving his Draft status and more about winning a championship.
"I just wanted to do well for my team, because I knew that if I did well, I'd help myself out individually, too," Skipworth said. "I wanted to go in and win a title for my high school team, and the team we have we can definitely do that. Everything I do is a domino effect with my team."
That included throwing his name into the Warriors' bullpen mix after a pitcher went down to injury. Skipworth, who can throw 90-92 mph and is strictly a fastball/changeup guy, will be the Patriot closer.
Kleveno said Skipworth's baseball IQ is what tips the balance in his favor.
"It's not his physical ability, it's being able to know the game," Kleveno said. "His leadership and knowing the game and making decisions -- he's baseball smart. He's got some baseball savvy. To have a kid that is so baseball smart is a once-in-a-lifetime for a high school baseball coach."
Skipworth has signed a letter of intent at Arizona State, but has his goals set elsewhere.
"I want to get started playing pro ball, so the likelihood of me actually going there and playing is slim," Skipworth said. "But I don't know what is going to happen June 5. College is still an option, but I want to play pro ball."
Mike Scarr is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.