With teammate Yadier Molina pitching to him, Holliday hit five home runs -- totaling 2,090 feet of distance -- on his first turn at the plate. Cardinals coach Dave McKay was initially slated to pitch to Holliday, but was replaced by Molina prior to the competition.
Holliday's total put him in a three-way tie for third place with Ortiz and Fielder, each of whom hand-picked his team for the Derby. As a result, each of the three players received five swings in a tiebreaker round. Holliday, going first, went deep on two of his five swings, but Ortiz topped him with four and Fielder went a perfect five-for-five.
It was the second straight year that Holliday fell just short of the second round. In 2010 in Anaheim, he also hit five first-round homers, which was the fifth-highest total -- one spot shy of advancing. In his only trip to the Home Run Derby before that, Holliday advanced to the second round in 2007, but fell one home run short of reaching the finals.
It appeared that Holliday might have been at a disadvantage on Monday because of the side of the plate from which he swings. All four semifinalists were left-handed hitters, while all four right-handed contestants were eliminated in the first round.
Holliday got off to a bit of a slow start on Monday, hitting ground balls on three of his first six swings and recording outs on six of his first eight -- any swing that doesn't result in a home run is considered an out for the Derby's purposes. He went deep on his first swing, barely clearing the wall in left field, but recorded outs on six of his next seven swings. His second homer, on his fifth swing, landed down the left-field line.
Even after that, he didn't start heating up just yet. He followed with a ground ball to the area of third base, a liner down the left-field line and a fly that fell short of the track in left. Holliday's third homer was a beauty, landing on the walkway behind the first deck in left field, 443 feet from home plate. Holliday was starting to feel it, as his next three outs were two line drives and a fly to very deep center.
And when the gold ball came into play, Holliday surged a bit. He hit a pair of homers to left field after his ninth out, raising $36,000 for the Boys and Girls Clubs of America.
After his 10th out, Holliday had to sit for quite a while. He watched eventual champion Robinson Cano blow past his total, but the next three players fell short of his number. The last two hitters of the first round, Fielder and Ortiz, matched him at five, necessitating the swing-off.
Holliday homered in his third and fifth swings of the tiebreak, but Ortiz and Fielder both topped him and Holliday was eliminated.
Matthew Leach is a reporter for MLB.com. Read his blog, Obviously, You're Not a Golfer and follow him on Twitter at @MatthewHLeach. This story was not subject to the approval of Major League Baseball or its clubs.