It’s time for my next installment in the process to select the Cardinals’ top players at every position during the 28-season Bill DeWitt Jr. Era of baseball, which encompasses the 1996-2023 seasons.

Yes, the 2023 season was awful for the Cardinals, but please have some perspective. Over the last 28 seasons, few MLB teams can match or exceed the Cardinals’ body of work and sustained success.

With DeWitt as the owner the Cardinals:

Rank fourth in the majors with 2,415 regular-season wins behind the Yankees, Dodgers and Braves.

Have won the most postseason games, 75, by a National League team and are second overall to the Yankees. Have competed in the most postseason games (150) among NL teams.

Are tied for third among MLB teams in league pennants won since 1996. The Yankees have won seven pennants, followed by the Astros (5), Cardinals (4), Giants (4) and Red Sox (4).

Are one of only six teams to win multiple World Series titles since 1996. Here’s the leaderboard: Yankees 5, Red Sox 4, Giants 3, Cardinals 2, Astros 2, and Marlins 2.

So far, I’ve made the Top 10 picks for starting pitchers and relievers – and the Top 5 in catchers, first basemen, second basemen, third basemen and shortstops.

Next: the top five left fielders plus honorable mentions. When doing research, I was surprised by the shortage of candidates at the LF spot. There were guys who played the position but it never was close to being their full-time home. Or they only played for the Cardinals for a couple of seasons – if that.

But one St. Louis left fielder played there for seven-plus seasons, was very productive, and served as a lineup fixture during a prosperous period of time for the team.

1. Matt Holliday. In one of his best trades, John Mozeliak sent a modest trade package to Oakland to acquire Holliday on July 24, 2009. And from the time of the deal until Holliday’s final season (2016) in St. Louis, the Cardinals led the NL in regular-season wins and were virtually tied with the Yankees for the best overall record in the majors.

The Cards also competed in 64 postseason games over that time – the most by an NL team – and their 32 postseason victories were second to the Giants. During this glorious stretch of winning baseball, the Cardinals made it to the postseason six times, advanced to the NLCS four times, and won a World Series and two NL pennants.

As a Cardinal Holliday was chosen for four NL All-Star teams, won a Silver Slugger award, and received Hall of Fame votes in four different seasons. During his peak – from the trade through 2014 – Holliday ranked 5th among MLB hitters in doubles, RBI and runs scored and was 23rd in homers. He batted .299 with a .385 onbase percentage and .504 slugging percentage and ranked 10th in the majors with a .889 OPS.

Holly had 90+ RBI in four seasons, two 100+RBI seasons, hit .300 three times, and had 20+ homers for five consecutive seasons (2010-2014.)

Holliday’s offensive stats made him one of the most productive outfielders in franchise history; he ranks fourth at the OF position in homers, ninth in extra-base hits, 10th in RBI, 11th in doubles and 11th in total bases.

During Holliday’s time with St. Louis, only catcher Yadier Molina accrued more Wins Above Replacement among the Cardinals.

Holliday was an exceptional hitter with runners in scoring position, batting .313 with a .408 OBP and .497 slug in those situations for the Cardinals. Per wRC+, Holliday was 45 percent above league average offensively when batting with runners in scoring position.

Three more things:

* During the DeWitt Era only Albert Pujols, Yadier Molina, Jim Edmonds, Matt Carpenter and Scott Rolen have more Wins Above Replacement than Holliday.

* Based on wRC+, the only St. Louis hitters to outperform Holliday since 1996 are Mark McGwire, Pujols and Edmonds. Per wRC+, Holliday was 41 percent above league average offensively as a Cardinal.

* Holliday was inducted into the Cardinals Hall of Fame in 2022.

2. Albert Pujols. During his first three MLB seasons (2001-2003), Pujols played 269 games in left field, logging 1,081 plate appearances at the position. And he was – of course – outstanding. When playing left field over the three seasons Pujols batted .347, blasted 94 homers, drove in 213 runs, and had a 1.082 OPS. Over a two-season stretch – 2002 and 2003 – Pujols ranked second to Barry Bonds in batting average among left fielders (.364), and was third to Bonds and Ramirez in slugging percentage (.635) and OPS (1.064). And Pujols did all of this in his age 21, 22 and 23 seasons.

3. Reggie Sanders. Walt Jocketty signed Sanders, age 35 at the time, to a two-year free-agent contract worth $6 million total. The investment paid off. Sanders played left field and right field for the 2004 and 2005 Cardinals teams that won 205 regular-season games and won the NL pennant in ‘04. Sanders played above-average defense over the two seasons and averaged 22 homers, 60 RBI and 18 stolen bases. As a Cardinal he slugged .507 with an .833 OPS and had three homers and 13 RBI in the postseason. In his two seasons as a Redbird, Sanders ranked fourth among the team’s position players with 4.1 Wins Above Replacement – and only Pujols, Jim Edmonds and Scott Rolen had more WAR. Sanders was a good player and somewhat underrated.

4. Ron Gant. Signing Gant to a three-year, $14 million contract was one of the first moves made by the Cardinals after DeWitt and partners purchased the franchise before the 1996 seasons. It was a good investment. With the Cardinals winning the NL Central division in 1996, Gant played a significant role by leading the team in homers (30) and finishing third in RBI (82). He slugged .504 and posted a .862 OPS. Gant was part of an impressive St. Louis outfield that featured Ray Lankford in center and Brian Jordan in right. In that 1996 season the three outfielders combined for 68 homers, 272 RBI and 70 stolen bases. In his three seasons with St. Louis Gant banged 73 homers and delivered 211 RBI.

5. Tyler O’Neill. This was a tough call. O’Neill’s St. Louis career has been filled with injury-related disappointment. But he also won back-to-back Gold Gloves in 2020-2021 and has the most Wins Above Replacement among St. Louis left fielders since coming to the majors in 2018. In 2021 O’Neill demonstrated his full talent when healthy by powering his way to a huge season: 34 homers, .560 slugging percentage, .912 OPS, 80 RBI and 15 steals. That season O’Neill led all MLB left fielders with 5.5 WAR and finished eighth in the NL MVP voting. The performance left us wanting more, but O’Neill’s chronic injury issues prevented a repeat. As a Cardinal O’Neill has a .458 slugging percentage and is 12 percent above league average offensively per OPS+.

Honorable Mention: Chris Duncan, Marcell Ozuna, Allen Craig.

Final note: I’ll be rolling out the center fielders and right fielders in the coming days … and both positions have been loaded with talent during the DeWitt Era.

Thanks for reading …


Bernie hosts an opinionated sports-talk show on 590 The Fan, KFNS. It airs 3-6 p.m. on Monday through Thursday and 4-6 p.m. on Friday. You can stream it live or access the show podcast on or through the 590 The Fan St. Louis app.

Please follow Bernie on Twitter @miklasz

All stats used in my baseball columns are sourced from FanGraphs, Baseball Reference, StatHead, Baseball Savant, Fielding Bible and Baseball Prospectus unless otherwise noted.