He exits having done better than them all.
McCutchen bowed out after the first round, as his four homers were not enough to advance in the three-round competition. However, his showing was better than the combined performances of the three Pirates to go before him.
Neither Jason Bay (2005) nor Bobby Bonilla (1990) were able to lift a ball over the wall during their Derby showings. Barry Bonds, in his last year as a Pirate, hit two home runs in the '92 competition.
"You only live once," McCutchen said shortly before taking the field. "I want to have a lot of fun. That's it."
McCutchen was a late addition to the Derby field, taking the spot that had been designated for Marlins outfielder Giancarlo Stanton. Knee surgery forced Stanton to sit out and sent National League Derby captain Matt Kemp looking for a replacement. That's when he called McCutchen, whose 18 home runs rank fourth in the NL.
One of McCutchen's first calls went to his Fort Meade (Fla.) High School baseball coach and longtime mentor, Jon Spradlin. Less than 48 hours after McCutchen invited Spradlin to pitch to him in the showcase event, there they were -- small-town baseball coach and national superstar -- sharing the same All-Star stage on Monday night.
Afterward it was hard to discern which one would come down from the high of the experience quicker.
"It's probably been the most overwhelming thing I've ever had to do," Spradlin said shortly after Detroit's Prince Fielder was crowned the Derby winner. "Even though his senior year was such a long time ago, I threw so much to him then that not a lot had changed."
Spradlin and McCutchen, a 2005 graduate of Fort Meade, have remained close since McCutchen began his ascension through the Pirates' system. McCutchen still has Spradlin, who has been on the Fort Meade coaching staff for 15 seasons, throw to him during the offseason.
It was during one of those sessions that Spradlin, facetiously, let McCutchen know he'd expect a call when the center fielder was eventually asked to participate in the Derby. And when the opportunity actually did arise, McCutchen never hesitated.
"He's been there for me whenever I needed anything, even in the Minors," McCutchen said. "I would say, 'Hey, I need somebody to throw me BP,' and he'd say, 'Hey, I'm there.' He would come out and throw to me regardless of when or where. He's been there for me."
When McCutchen, who hit fifth during the eight-player first round, stepped up, Spradlin targeted the inner half of the plate. McCutchen's plan was to make sure he took some pitches, something that would elongate the experience and help him get into a groove with his timing.
Spradlin, after bouncing his first pitch to McCutchen, seemed to settle in well.
"It was all good when I did the warmup pitches," Spradlin said. "Then all of a sudden, it went live, and he got in the box, and it was pretty overwhelming there for a few minutes. I didn't want to screw it up for him."
Both could exhale after McCutchen's third swing, which resulted in a 435-foot homer that dropped over the wall in left-center.
"It's getting that first one out of the way," McCutchen said. "Then you get a feel for your coach. You get a feel for where the ball is carrying and a feel for your swing."
McCutchen's second blast -- a 436-foot shot -- landed just a little farther to the left. His final two home runs -- one measuring 412 feet, the other 400 feet -- came when he was down to his final out.
McCutchen fell one home run short of matching Fielder's first-round total. Had the two tied, there would have been a swing-off to determine which one would advance to the second round. As it was, Fielder moved on, along with the Blue Jays' Jose Bautista (11 homers), the Cardinals' Carlos Beltran (seven) and the Angels' Mark Trumbo (seven).
Bautista and Fielder later advanced to the Derby final, which Fielder won, 12-7.
Both McCutchen and Spradlin remained at Kauffman Stadium through the event's conclusion, the two enjoying every minute of an opportunity that they know might not come again. Although McCutchen is expected to be a perennial All-Star, he understands that it will be harder to again break into the Derby field.
"It can be a once-in-a-lifetime opportunity for me," McCutchen said. "It could be the only time I ever do the Home Run Derby. I took advantage of it. It was something I wanted to do. I definitely enjoyed it."
As for Spradlin, he and his father-in-law will remain in Kansas City until Wednesday, soaking in all that they can. They will also be at Kauffman Stadium to watch the pride of Fort Meade participate in Tuesday's 83rd All-Star Game.
Spradlin seemed to be extending his stay on Monday, too. Several minutes after coming off the field, he was still wearing his All-Star jersey.
"This is going to hang up forever," Spradlin said. "I don't even know if I want to wash it and mess anything up. I'm definitely going to hang onto it."
Jenifer Langosch is a reporter for MLB.com. Read her blog, By Gosh, It's Langosch, and follow her on Twitter @LangoschMLB. This story was not subject to the approval of Major League Baseball or its clubs.