Five years later and nobody is complaining.
The Cardinals are in the postseason for the fifth time in the six Octobers Holliday has been with them, and this year, more than ever, Holliday was a critical cog in their late-season surge to a National League Central title. They open the NL Division Series against the Dodgers at Dodger Stadium on Friday at 5:30 p.m. CT (watch on FOX Sports 1) in a rematch of last year's NL Championship Series.
These aren't your Cardinals of recent years, the team that was so good at creating offense. These Cards relied on pitching and defense to stay in the NL Central race. And then, in the final six weeks, Holliday started to hit like, well, Holliday.
The Cardinals not only overtook the Milwaukee Brewers to win the division, but they also held off a late charge by the Pirates.
"Holliday's [resurgence] was in sync with our team changing its trajectory," said general manager John Mozeliak. "You look at it month to month, and we were consistent but we never took that step up. His bat got hot, and that allowed our team to make that move."
The numbers don't lie.
The Cardinals were 66-57 at the end of play on Aug. 17, the 10th-best record in baseball. They had scored 461 runs in 123 games, which ranked 29th out of the 30 big league teams. The Cards had gone .500 (14-14) in April, and they were never more than three games better than .500 in May (15-12), June (14-13) and July (13-11). St. Louis won nine of its first 16 games in August.
And Holliday? He was hitting .260 on Aug. 17. He had hit 12 home runs, driven in 59 runs and played in 119 games.
In the next six weeks, the Cardinals went 24-15, scoring 158 runs in 39 games.
And Holliday? He hit .309 with eight home runs and 31 RBI in 37 games, the third-most RBIs in the Majors over that stretch.
"It's a long season, so you keep grinding," said Holliday. "You look for ways to help the team win. You try and do little things to feel like you are contributing.
"It's about experience. You learn how to handle situations from having been through them. It's all part of the process of playing the game. You know it's a long season. You just keep pushing."
Sounds so easy. But then, Holliday makes it look easy. He's big, he's strong and he is athletic.
Holliday was rated the third-best high school quarterback in the country when he came out of Stillwater (Okla.) High School in 1998. He had a pile of big-time offers and committed to Oklahoma State, where his father was the baseball coach at the time. Holliday, however, opted to sign with the Rockies, who selected him in the seventh round of the 1998 First-Year Player Draft but gave him an $840,000 bonus, at the time the record for that late of a pick in the Draft.
No regrets with that decision. And no regrets from Holliday and the Cards with the decision for him to make his commitment to remain in St. Louis five years ago, even if Mozeliak was second-guessed by many in the media, and even some of his peers, for giving Holliday that kind of deal before he worked out an extension with Albert Pujols.
Mozeliak, however, didn't hesitate.
"How often do you get the opportunity to get a player who swings a bat like that?" said Mozeliak. "How often do you develop at bat like that? It's rare.
"We had the opportunity to sign him and make sure he stayed with us. We hoped at the time we could sign [Holliday and Pujols], but what happens if we signed neither? Where would we be now?"
Turned out the Cardinals weren't able to sign Pujols. They made what they felt was a strong offer, but Pujols signed a 10-year, $240 million deal with the Angels -- three years longer and double the money of the deal Holliday signed.
But then, Holliday didn't try and push the market to the max.
"I got to play there for those two months before free agency," he said. "I saw what the organization was about. Everything was done to win. I got to spend time with players like [Adam] Wainwright and Yadi [Molina]. That appealed to me, and obviously it was a fairly laid-back city, something I was comfortable with having grown up in Oklahoma."
Nothing has happened since to give either the Cards or Holliday any regrets.
"We've been in the postseason [all but one year] since I have been here," Holliday said.
And Holliday has been a key part of that success.