Both had been claimed off waivers in the offseason -- Wilson in December, Olmedo on the first of February -- and both had fluctuated between the Majors and Minors in recent years, never quite able to make it permanent but still showing flashes of potential.
But much has changed since mid-February. Olmedo is no longer with the club, having been claimed off waivers by the Phillies shortly after camp opened. And shortly after, non-roster invitee Luis Rivas quickly entered the mix as the biggest competition for that backup spot.
However, even though Rivas appears to have taken the position as frontrunner in the position for that backup spot, Wilson isn't quite ready to concede.
He has looked adequate on defense in the 16 games he has played this month, though his offense has not kept up that pace. In contrast, Rivas came into Friday's contest against the Reds having hit safely in 10 of the 14 games he has played in.
"I've been doing alright," said Wilson, who entered Friday's game with just six hits in 33 Spring Training at-bats. "I haven't really been hitting the way that I should. As far as hitting goes, though, it's still early. Sooner rather than later, I'll get that figured out."
It's arguably now not so much when as where Wilson will get that figured out. If he comes out the winner in the middle infield battle, then that answer is simple. He'll play in his hometown of Pittsburgh, wearing the uniform that his baseball idols growing up used to wear.
"It definitely always was my dream as a little kid to play for the Pirates," said Wilson, a 1999 Mount Lebanon High School graduate. "I always hoped I would get the chance to play in Pittsburgh, and sooner rather than later."
But the circumstances drastically change if Wilson is left off of the team's 25-man roster.
Wilson has no more option years, meaning that if he is not on the team's Opening Day roster, he would have to clear waivers before the team could send him down to Triple-A Indianapolis.
General manager Neal Huntington acknowledged earlier this spring that he feared that making Wilson available on waivers would be a significant risk. When the Pirates claimed the middle infielder off waivers from Tampa Bay, there were numerous other big league clubs that also had interest in him.
That was part of the reasoning behind making Olmedo the one available to be claimed off waivers -- rather than Wilson -- when the team needed to clear a roster spot for Byung-Hyun Kim back in February.
If that same interest is still there, then the Pirates may not have the luxury of keeping Wilson in their organization. And Wilson's hope of one day playing for the Pirates would be over for the present time.
Regardless, Wilson said he hasn't put much thought into his status.
"It's the way the game works," said Wilson, who has played in 116 Major League games in his career. "If it doesn't work out here, hopefully it means that it works out for me somewhere else. If not, Triple-A isn't the worst thing."
He even added that though the dream of playing at PNC Park remains strong, he is prepared to sacrifice that possibility if it means a more open path to the Majors elsewhere.
"I know [shortstop prospect] Brian Bixler will be down [in Triple-A Indianapolis], and I'm not sure what chances I'd have to play," Wilson said. "I hope that whatever happens will be the best opportunity would be for me in terms of playing time."
But make no mistake, Wilson's central focus right now remains squarely on making the Major League club. He had his first significant taste of big league play a year ago when he combined to play in 105 games with Washington and Tampa Bay. During that stint, Wilson hit .238, but made 22 errors.
Wilson said he is hopeful that Rivas' re-emergence this spring has only pushed him to improve in both of those areas, even if it means that Rivas snatches away that bench spot that Wilson had hoped would be his.
"There's always competition -- there's no hard feeling," Wilson said. "If Luis makes the team and I don't, then I'm happy for him. He's a great player. He's had good experience in the big leagues. The way he's playing right now, he's playing like he wants to make this team."
"It's been awesome," he added. "To show up with a Pirates jersey on every day has been pretty cool."
Jenifer Langosch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.