He had been a standout pitcher at Freedom (Pa.) High School in his younger days before making the transition to Allegheny College, where he again quickly made a name for himself.
His climb up the Pirates' organizational ladder was much of the same, with confidence breeding success and promotions appropriately following.
But lately, it's been one lesson after another in adversity for the right-handed pitcher from Freedom, Pa. And it's not necessarily about to get any easier.
Sharpless' outing on Wednesday was his last in big league camp this spring, as he earned the not-so-notorious distinction of being the first pitcher reassigned to Minor League camp for non-injury related reasons.
Despite the openings that the Pirates have in their bullpen, general manager Neal Huntington said that the determination that Sharpless would not be in position to compete for one of those spots came long before Thursday's demotion, however. The decision was easy, Huntington said, because Sharpless simply didn't come into camp in the necessary physical condition to compete.
"To come out and compete with the numbers that we have, he didn't put himself in the best position to be able to do that," Huntington said. "If we were in a normal situation with not 30 pitchers in camp, he probably would have been fine. But we've got too large a number of pitchers that everyone needed to be ready to go right out of the chute. He didn't put himself in that situation."
This challenge to improve his physical condition and this early demotion comes after a tumultuous 2007 that Sharpless, in his own words, called "a disaster." And both are sure to make his climb back up toward being a candidate for the big league roster that much harder.
It's yet another setback in a year that has been defined by them.
Back in November, Sharpless was removed from the team's 40-man roster so that the organization could protect some of its other players from potentially being taken in the December Rule 5 Draft.
And even before that disappointment struck, there was Sharpless' initial introduction to true on-the-field adversity.
He spent a total of 20 days with the Major League club midseason last year, making six appearances during that brief stay. He allowed the opponent to score in four of those six games and gave up three homers in just 4 1/3 total innings before being demoted.
His time back with Triple-A Indianapolis wasn't shining either. The struggles continued. The mental edge Sharpless used to have diminished even further. The confidence was nearly void. His results were so suspect that he wasn't even among those considered for a callup in September.
"I lost that confidence, and I lost that edge," Sharpless said, trying to put into words what he experienced last season. "I second guessed myself out there. I was all messed up out there."
What's interesting, however, is that all of these struggles came after Sharpless had been so successful all the way through his climb up the Minor League ladder. He was in Double-A by the time his second full professional season ended. And he had been in Pittsburgh a year later.
So what exactly has happened to a once promising arm in the system?
In Sharpless' own words, the downhill turn he took started, ironically, after a scoreless outing in his 2006 Major League debut. He got out of that Aug. 1 game against Atlanta unscathed, though he did so after having walked the bases loaded.
Sharpless shrugged off the control issues as simply a result of nerves. The Pirates coaching staff saw it as something different. They wanted to change Sharpless' motion.
They worked on taming his high arm angle, adjusting his landing and changing the motion of his back leg. The goal was for Sharpless to have a more fluid arm motion. But for Sharpless, it simply became a forced adjustment that he never adapted to.
"The reason I got to where I am was [because] I don't throw like that. I throw and it's awkward. I don't have the velocity like a Matt Capps," Sharpless said. "We were working with some things that they thought would be better for me. Maybe they would have, but when you're first trying to get to the big leagues and trying to establish yourself and then you try to change some things, that's when you get all frustrated."
The result of this adjustment wasn't found solely on the scoreboard. Its fingerprints were left all over his mental state, as well. Sharpless no longer had it.
So what was done is now in the process of being undone. Sharpless has been given the green light to decide on what he wants to do based on how he feels and not based on what he's been told. The goal, said pitching coach Jeff Andrews, is to piece back together Sharpless' confidence while he simultaneously rediscovers his mechanics.
"He's kind of been given the freedom to get it back any way [he] can," said Andrews, who has worked with Sharpless for parts of the last three season. "You have to have both [comfort and confidence], and you can't if you're paralyzing yourself and analyzing what you're trying to do."
Though he knows he is starting over in some respects, Sharpless said he is just relieved to be doing so on his own terms. He said he believes he has gotten over the seemingly endless frustration. And he insists that he's not bitter about the detour his career has recently taken.
"I've never experienced having that failure. I've always done well until last year, and I think that was good for me," Sharpless said. "I think you need to go through something like that in your lifetime, whether it's in life or in baseball. I think it makes you stronger as a person and as a player.
"Always believe in yourself," he continued. "No matter how bad things get, your family still loves you, your friends still love you, you'll still wake up in the morning. That used to be hard for me to understand."
Jenifer Langosch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.