He grew up on these streets. He ran these playgrounds. He earned his first dollar of scholarship money out of a rookie contract that paid him $15,000 a year — and he gave $1,000 of it back. That is the measure of a man. That is the measure of Dave Winfield.
This month, the annual Winfield Awards scholarship banquet returns to St. Paul for its 50th year — a milestone that warrants both celebration and reflection. For half a century, the Winfield family has been doing quietly what this city has talked about loudly: investing in Black and brown student-athletes, recognizing their whole selves, and sending them forward.
David Mark Winfield was born October 3, 1951, in the Rondo community of St. Paul, Minnesota — a neighborhood defined by the cultural and intellectual richness of its Black residents, and then defined again by the 1956 destruction of Rondo Avenue by Interstate 94. The freeway took the heart of the community. The community rebuilt its spirit anyway. Dave Winfield is a product of that resilience.
“I didn’t know any English when I first came here, so being here is really important for me.” — Hte Mow Chaw, Humboldt High School, Winfield Award recipient
He and his older brother Steve were raised by their mother, Arline V. Winfield, a single woman of formidable strength. When Steve Winfield spoke at Dave’s legacy celebration at Toni Stone Stadium in St. Paul in July 2025, he recalled what it was like growing up without much — and how they always tried to find something extra to give when a new teammate showed up with nothing. That impulse toward generosity did not diminish when they made it. It grew.
Dave attended St. Paul Central High School, where he earned All-St. Paul and All-Minnesota honors in both baseball and basketball. He went on to earn a scholarship to the University of Minnesota, where he starred in both sports, won a Big Ten basketball championship, earned All-American honors in baseball, and was voted Most Outstanding Player of the 1973 College World Series — as a pitcher.
He was then drafted by four professional leagues in three sports: the San Diego Padres (MLB), Minnesota Vikings (NFL), Atlanta Hawks (NBA), and Utah Stars (ABA). He chose baseball. He walked directly to the major leagues without a single day in the minors. And he never forgot where he came from.
“The angle was that I was appreciative of what people did for me. I couldn’t have made it by myself.” — Dave Winfield
In 1973, his first season with the Padres, he began buying blocks of tickets so families who could not afford games could still attend. By 1977, he had organized those efforts into the David M. Winfield Foundation for Underprivileged Youth — the first 501(c)(3) charitable foundation established by an active professional athlete in American sports history. He was 25 years old.
That same year, he and Steve launched the Winfield Awards — a scholarship recognition program for student-athletes of color in St. Paul who excel academically, athletically, and in their communities. The scholarship has since honored more than 400 students from St. Paul’s high schools.
The structure of the award matters as much as the money. Recipients are selected from schools across the city. The recognition is built on three pillars: academic achievement, athletic excellence, and community involvement. It insists on the whole student. It insists on the whole human being. In a society that often reduces Black and brown youth to their athletic potential alone, the Winfield Award has always said: that is not enough, and you are more than enough.
The 49th Annual Winfield Awards banquet was held June 1, 2025, at the Intercontinental St. Paul-Riverfront Hotel, honoring 20 student-athletes from 10 St. Paul high schools. Steve Winfield, who has served as committee chair since the beginning, has anchored the program through five decades of leadership on the ground. He built this not from a penthouse suite or a foundation boardroom, but from the same St. Paul soil he and his brother grew up on.
“David was doing it before it was a popular thing to do.” — Steve Winfield
The 50th Annual Winfield Awards arrives this spring as something genuinely historic. Fifty years of scholarships. Fifty graduating classes of student-athletes who heard, perhaps for the first time, that their community saw them — not just as players, but as scholars and citizens. That is not a small thing. That is a generation of young people who carried that recognition into their adulthood, their careers, their own families.
The broader arc of the Winfield family legacy took on new dimension in July 2025, when St. Paul Mayor Melvin Carter announced at Toni Stone Stadium that a statue of Dave Winfield would be placed in the Hall of Fame Plaza at Dunning Sports Complex. Statues of fellow St. Paul Major League Baseball Hall of Famers Paul Molitor, Jack Morris, and Joe Mauer are planned as well — four sons of St. Paul, honored in bronze in the city that made them. The plaza will be a gathering of giants.
That day, Mayor Carter said something that stopped the room. He reminded those gathered that of some 20,000 men who have played Major League Baseball, only 33 have accumulated 3,000 hits. Dave Winfield is among them. “When we say Dave Winfield is literally one of the best to ever do it,” Carter said, “that is not hyperbole at all.”
Dave Winfield was inducted into the Baseball Hall of Fame in 2001. He is a 12-time All-Star, a seven-time Gold Glove Award winner, and a six-time Silver Slugger. He drove in the series-winning runs with a two-run double in the 11th inning of Game 6 of the 1992 World Series. He recorded his 3,000th hit with the Minnesota Twins, in his hometown. He hit his 400th home run against the Twins. These are the bookmarks of a cathedral career.
But Steve Winfield, who has never played an inning in the major leagues, may have built the more enduring legacy right here, every spring, in a hotel ballroom on the banks of the Mississippi. Fifty years of showing up. Fifty years of calling the names.
The Winfield Award ceremony has always been a community event. It draws family, school administrators, coaches, city officials, and friends. It draws former recipients who are now parents, educators, and civic leaders themselves. Former Mayor Melvin Carter is among those who attended college on a Winfield scholarship. That is the compound interest of community investment.
Insight News has covered St. Paul’s Black community for more than five decades. We know that what the Winfield family built is rare. It is consistent. It is accountable. It is personal. Dave Winfield took $1,000 from his first professional paycheck and started a scholarship. He never stopped. Neither did Steve. And as this community prepares to gather again this spring for the 50th Annual Winfield Awards, we say: that means something. That means everything.
For information on the 50th Annual Winfield Awards, contact the event organizers. For those wishing to support the scholarship fund, visit davewinfield.io.
“This neighborhood that raised legends continues to make history.” — Anika Bowie, St. Paul City Council, Ward 1
This article was produced with AI assistance.
