Jeff Winchester still agonizes over what he did to Matt Holliday.

Winchester, a first-round pick at catcher by the Colorado Rockies in the 1998 MLB Draft, shares his 1999 Topps and Topps Chrome rookie cards with the team’s seventh-round selection from that class. It just so happened to be Holliday.

Holliday, who was incorrectly listed as a first-round pick on the back of the card, developed into a seven-time All-Star outfielder and World Series champion with the St. Louis Cardinals. Winchester never cracked the majors, spending nine seasons in the minor leagues before retiring in 2006. Given their draft slots, collectors in the late ’90s probably assumed Winchester would be the blue-chip prospect, and Holliday the MLB longshot.

“Who would have thought, right? A guy who is probably going to find his way into the Hall of Fame is stuck with somebody who’s bringing his card value down, man. I feel bad for Matty,” Winchester told The Athletic in jest.

When I told Winchester I bought his 1999 Topps Chrome rookie card two months ago for $1.83, Winchester said, “Oooh, you got ripped off!”

“I had to pay a little extra for shipping,” I said, feeling obligated to tell my high school buddy since I was among his family and friends at his parents’ home the night the Rockies drafted him.

“So that’s where the $1 came from,” Winchester said. “My kids used to take my cards and put them in their bicycle spokes because they liked the way that it sounded when they were riding down the street.”

Before his cards became spoke accessories and between playing Danny Zuko in “Grease” and Colonel Nathan R. Jessep in “A Few Good Men” in plays at Archbishop Rummel High School in Metairie, La., Winchester became one of the greatest high school baseball players ever in the New Orleans area.

As a junior, he helped guide Rummel to a Class 5A baseball state championship in 1997. He earned the Gatorade State Player of the Year honor in his senior season. Legendary LSU coach Skip Bertman offered Winchester a scholarship to play for the Tigers. This was in the midst of LSU becoming a baseball dynasty, having won College World Series titles in 1991, 1993, 1996 and 1997.

The choice would’ve been a no-brainer … until the MLB Draft.

The Rockies selected Winchester at No. 40, a sandwich first-round selection, dangling a signing bonus north of $500,000 in front of him. No New Orleans area baseball player has been drafted higher than Winchester straight out of high school since him. He’s the highest drafted New Orleans area prep player in the past 40 years. Factoids, none of which Winchester knew.

Other notable players drafted behind Winchester in 1998: Adam Dunn, Mark Prior, Barry Zito, Aubrey Huff, Eric Byrnes, Mark Teixeira, Juan Pierre, Eric Hinske, Adam LaRoche, Cliff Lee, Ryan Braun.

And of course, Holliday.

The combination of the draft slot, signing bonus and promise that the Rockies would pay for college if Winchester decided to either attend during the offseason or if his career didn’t pan out, Winchester opted to sign with Colorado and head off to rookie ball in Arizona rather than go to Baton Rouge for three years before another shot at the MLB Draft.

Almost 30 years later, people still ask him about that decision, given that he lives an hour away from campus in Mandeville, La. He would have been part of LSU’s national championship team in 2000.

“I’ve got to be honest with you. There are times where I do sit back and I wonder where I would be in life in general had I decided to go to LSU,” Winchester said. “I definitely think that I wouldn’t be the same person that I am today. Mainly because I feel like the amount of humility that I experienced going through professional baseball, I think that was a very grounding thing for me. I really do feel like that in itself kind of helped shape me a little bit more and make me grow up a lot more than where I was when I felt like when I was in high school.

“It was kind of a turning point for me, going through what I went through with professional baseball, given how much of a struggle it was. I tried to be grounded, but there’s moments where sometimes as individuals, we get caught up in some of the hype and stature. You can get lost in it a little bit. I definitely think my time in minor league baseball, it always kept me in check because the moment you feel like you’re on top of the world, the game finds a way of humbling you.”

Winchester’s nine-year minor league run took him coast to coast: Tucson, Ariz., Asheville, N.C., Salem, N.C., Visalia, Calif., Tulsa, Okla., Huntsville, Ala., Reading, Penn. and Clearwater, Fla. His journeys brought him to some minor league All-Star games and league championships. Winchester played a couple of minor league seasons with Holliday, as well.

Winchester’s career never progressed past AA, though. Winchester took off his jersey for the final time in 2007 after his final big league Spring Training call-up game, walking into the Philadelphia Phillies’ Single-A affiliate player development office and said he was done. Winchester hopped in his car and drove back home to Louisiana. He hit 64 home runs and tallied 307 RBIs with a .227 batting average for his minor-league career.

Meanwhile, Holliday was in his third season with the Rockies, on his way to his first All-Star Game nod the same season Winchester retired.

“I gave it a run. I felt like I did my best,” Winchester said. “It just turned out that it wasn’t in the cards for me to be a ballplayer.

“I had to figure out what else to do in life.”

That meant moving back to the New Orleans area and taking up the Rockies’ offer in his contract that the team would pay for college. While taking classes at the University of New Orleans, Winchester would give private baseball lessons. The father of one of his players offered Winchester a job in orthopedic sports medicine sales. It eventually turned into his post-baseball career.

But his true first step upon returning to southeast Louisiana was being a father, not stuck on the road in the minor leagues. Winchester has settled into that role so much that he’s been a baseball dad — along with baseball wife, mom and high school sweetheart Brandi — ever since. His older son, Cooper, plays college baseball for the Air Force. His younger son, Carter, is a high school standout at Mandeville (La.) High.

Meanwhile, Winchester is still part of a text message thread with Holliday and many of their fellow minor-league teammates. Winchester and Holliday have also crossed paths in travel baseball across the country as Holliday followed his sons Jackson (now with the Baltimore Orioles) and Ethan (2025 MLB Draft No. 4 pick by the Rockies).

Holliday (left) with Winchester in 2023. (Photo courtesy of Jeff Winchester)

Multi-player rookie cards were common in older baseball sets, specifically in the 1960s. Some of the more famous multi-player rookie cards from that decade included Nolan Ryan (who shared a card with Jerry Koosman, who would have a distinguished career in his own right), Pete Rose (Pedro Gonzalez, Ken McMullen and Al Weis), Tom Seaver (Bill Denehy), Steve Carlton (Fritz Ackley), Joe Morgan (Sonny Jackson), Jim “Catfish” Hunter (Rene Lachemann, Johnny Odom and Skip Lockwood), Don Sutton (Bill Singer), Rod Carew (Hank Allen), Johnny Bench (Ron Tompkins) and Rollie Fingers (Bob Floyd and Larry Burchart).

The multi-player primary rookie card trend didn’t disappear, but it slowed down as the hobby entered the mid-1980s. Ultra modern cards still pair top prospects, but they’re usually within insert sets rather than primary rookie cards.

The irony is that Holliday’s top 10 most expensive public card sales via online trading card price guide Card Ladder are all dual-autographed cards with Jackson. The most expensive card went for $3,000 in February 2024.

Meanwhile, Winchester’s most expensive card sale with Holliday went for $55.45 in April 2025. Winchester never became a major-league player like Holliday, but he still carries legendary status in the New Orleans area.

“People will say that they remember the name,” Winchester said. “I always question where they heard the name from because that can change the context. But I still get people saying they remember seeing me play. I love to go out to the mailbox, and I’ve still got people who are sending me cards.

“I think everybody’s a part of this one big Facebook group where when somebody sends a card to an address that they find online, and then that person reports back to the group that, ‘Hey, this person actually did sign my card and send it back to me.’ Then everybody now knows that you can send it, and Jeff Winchester will send you back their card.”

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