But that storybook start didn't end with such grace as the Rockies fell to the Red Sox, 15-5, on Wednesday night. A sellout crowd of 48,775 packed in to see that smooth left-handed swing one last time.
Helton pointed to the crowd as he rounded first base and the ball dropped into the right-field seats in the second inning. His No. 17 etched into the outfield grass, painted by each dugout and inscribed into the mound, it felt like the next scene in a carefully choreographed play. The curtain call that followed only added to the spectacle.
The moment was something Helton could only dream of, a situation not fit for the confines of reality.
"It was kind of surreal," "I hit it and I'm like, 'That's a homer.' But I really wasn't sure," said Helton, the No. 17 on his jersey blanketed in a fresh dirt stain. "I thought, 'That couldn't really happen.'"
The Jumbotron flashed tributes from former teammates Jason Giambi and Clint Barmes, his longtime manager Clint Hurdle as well as Denver Broncos quarterback and close friend Peyton Manning. The reserved Helton, who reveals little emotion on the field, admitted it was those moments that brought him close to tears.
" I threw maybe 10 balls in right field playing catch because I was watching the video board the whole time," right fielder Michael Cuddyer said. "Tonight, it was tough being a player because I was a fan first."
Helton provided another great memory in the fifth, losing his helmet as he slid into second headfirst on an RBI double -- the 592nd of his career -- off the top of the left-field wall. Despite having runners on first and third with no outs, the Rockies didn't score after Yorvit Torrealba grounded into a double play.
"I talked about him rising to the occasion on this homestand and tonight was an incredible encore for him," Rockies manager Walt Weiss said.
As his career nears the end, Helton's shown flashes of his former dominant self. Helton's riding a seven-game hitting streak heading into the final three games of the season in Los Angeles and Wednesday marked his third-straight multi-hit game.
"Just to close out his home career with a night like tonight, certain players have a flair for the dramatic, and seemingly that was one tonight," Red Sox manager John Farrell said.
Despite their best attempts to send off their icon with a victory, the seven runs that starter Jhoulys Chacin (14-10) allowed over four innings proved too much to overcome. Jacoby Ellsbury led off the game with a single and Shane Victorino reached on a bunt, setting up David Ortiz's two-run double. Jarrod Saltalamachia added an RBI single to put Boston up 3-0 in the first.
As if imitating Helton fighting off pitches on a 1-2 count, the Rockies rallied with two more runs in the third. Nolan Arenado lifted a two-out double to right to knot the game at 4 after Helton drove in his second run with a sacrifice fly to left-center that scored Charlie Blackmon.
But Victorino sunk Colorado back into a three-run hole with a three-run homer in the fourth.
Reliever Rob Scahill fared no better than Chacin, giving up two hits to open the fifth before Will Middlebrooks launched a three-run, opposite-field shot to give the Red Sox a 10-4 lead.
Peavy (12-5), a longtime member of the Padres and familiar opponent to Helton, gave up five runs over six innings and whiffed five. The first baseman finished his career against the right-hander with a .360 average, four homers, seven doubles and seven RBIs.
Roy Oswalt served up a grand slam to Middlebrooks in the eighth.
But in the end, the final score was an afterthought.
In the top of the ninth, Helton's daughters Tierney and Gentry raced onto the field and took the first base lined with a purple stripe and his number. He called that the "highlight of his night" in a game full of them. He waved goodbye to the crowd as he sunk into the dugout one last time, making one final lap around the field in the ninth for fans to savor.
The Red Sox patiently waited for him complete the lap, expressing the same admiration his teammates did for the legend he's become in Colorado. Amid all the jubilation and precious moments, the other players in the dugout were forced to realize they will one day have to leave this game behind, too.
"It was kind of sad to see one of your teammates go and at the same time, you think about [how] it's going to happen to other players," left fielder Carlos Gonzalez said. In the seventh, the Helton fouled off two pitches, never letting a ball simply slide into the strike zone, but whiffed on a 95-mph fastball from Franklin Morales in his final home at-bat.
"They're all special," Helton said. "I'm going to hopefully remember all of them, remember the whole night. Everything about it was great. If we would've won, it would've been perfect."