Exactly two weeks after Grilli signed his new deal, the Pirates traded former All-Star closer Joel Hanrahan to the Red Sox, opening the door for Grilli's promotion.
"It's very relaxing knowing that you don't have that monkey on your back trying to prove yourself," said Grilli, who stopped by the MLB.com headquarters on Friday to field questions from fans via social media and a live video stream inside the Edward Jones Chatting Cage. "And it's obviously nice to have a two-year contract behind you and an organization that believes in you and says, 'This is your job.' I've never really had that in my career."
Instead, Grilli has spent the past 16 years trying to live up to the expectations of being a 1997 first-round Draft pick. Taken by the Giants with the fourth overall pick, Grilli was traded two years later to the Marlins without making an appearance for San Francisco's big league club.
He eventually made his Major League debut with the Marlins on May 11, 2000, but that would be his only big league appearance that season. Then, after six appearances in 2001, he wouldn't appear in another Major League contest until Aug. 27, 2004, after the White Sox had selected him from the Marlins in the Rule 5 Draft.
"When you're a first-round pick, you have not only big expectations of yourself, but the organization does as well," Grilli said. "I started bouncing around, had some peaks and valleys, injuries, falling behind -- it's been a tough journey. It all made me better suited for the role I have now, though."
Even in Chicago, Grilli was still a long ways off from achieving any career stability. He went 2-3 with a 7.40 ERA in eight starts with the White Sox in 2004 and was released at season's end.
After his release from the White Sox, Grilli spent time in the Tigers, Rockies, Rangers, Indians and Phillies organizations before signing with the Pirates on July 21, 2011 -- one day after being released by Philadelphia.
The Phils had turned Grilli loose after 28 appearances with Triple-A Lehigh Valley, despite the righty going 4-1 with a 1.93 ERA and 43 strikeouts in 32 2/3 innings of work.
"After that, it was just like, 'What do I have to do?'" Grilli said. "I almost went to Korea, just because I had to make money -- this is the way I support my family -- so it's been crazy."
One day after signing with the Pirates, Grilli took the hill and tossed one scoreless inning of relief. He hasn't left the Majors since.
By the end of the 2011 campaign, Grilli had made 28 appearances out of the Pirates' bullpen, tallying a 2.48 ERA over 32 2/3 innings. One year later, Grilli made a career-high 64 appearances, notching a 2.91 ERA and 32 holds while setting up for Hanrahan. More importantly, Grilli impressed the Pirates' front office enough last season to make it feel comfortable going through with the Hanrahan trade in late December.
"I was excited as well as maybe a little bit anxious -- in a good way. Not nervous like, 'Oh, can I or can't I do this?' I knew I could," Grilli said about assuming the closer's role. "It's still getting three outs, just in a different inning with a lot more pressure."
That added pressure on the field, however, has seemingly been erased by his long-awaited stability off of it. Though Grilli entered in a tie game and conceded a walk-off hit in Thursday night's loss to the Mets, he remains a perfect 13-for-13 in save situations this season.
Between making his third appearance for Team Italy in the World Baseball Classic this spring and the daily rigors of being a Major Leaguer, Grilli admitted he hasn't had time to let his new role fully sink in. Yet given what he's been through to get there, Grilli said it's hard not to appreciate where he is right now.
"I've just got my head down and the foot straight on the gas pedal. Whether it's a good season or bad season, I don't look up until it's over," Grilli said. "I definitely have an appreciation for where I am now and what it's taken to get to this point, but I don't think I fully reflect on these things until the season is over.
"For now, I'm just having fun with it all."