About Dr. Preston R. Winfrey
Reverend Dr. Preston R. Winfrey has been Pastor of the Pioneer Missionary Baptist Church of South Holland, Illinois, since November 1981. This coming November, he will celebrate his 44th year as Pastor and will be retiring as Senior Pastor after 44 amazing years, having moved the congregation from Calumet Park, Illinois, to South Holland, Illinois, in 2008. He is the son of Nellye Winfrey and Arthur Winfrey and is the 6th of seven children.
Dr. Winfrey is a native of Chicago, and is married to Dr. Gloria J. Winfrey, a retired Chicago Public School Assistant Principal. He is also a father, grandfather, and great-grandfather. Dr. Winfrey attained his Elementary and High School education in the public schools of Chicago. He attended the School of Business Management in San Antonio, Texas. He earned an Associate of Arts Degree from Chicago Baptist Institute in Theology and majored in Psychology at Chicago State University. He earned his Bachelor of Theology and Master of Theology Degrees, and in November 1997 earned the Doctor of Theology from the Andersonville Baptist Seminary of Camilla, Georgia.
As a busy pastor, Dr. Winfrey finds the time to be involved in civic, social, and religious endeavors. He was the first elected President of the Charles S. Deneen Elementary School Local School Council while also serving as President of the Parent-Teacher Association. He was instrumental in securing a new roof, replacement of windows, and the removal of asbestos from the building, as he presented the needs before the Chicago Public School Board on February 25, 1987. He also served several terms on the Chicago Citizens’ School Committee.
Among his many activities, he served as the Organist for the Progressive National Baptist Convention, Inc. at the request of Past Presidents, Rev. Dr. J. Alfred Smith, Sr., Rev. Dr. Fred C. Lofton, Rev. Dr. B. W. Smith, Sr., and Rev. Dr. C. Mackey Daniels.
Additionally, he is:
- Instructor for Pastoral Search Committees (average of 2 per year) since 1990
- Currently serving as Chairman of the Curriculum Committee PNBC, Inc.
- Past President of the Congress of Christian Education for Local, State, and Regional levels.
- Past Vice-President of Christian Education of the P.N.B.C. Inc..
- Past President of the Parent Body, Baptist State Convention of Illinois, Inc.; (Member)
- Member of the Union District Baptist Association of Chicago and Vicinity, Inc., and past Moderator serving two separate tenures.
- Former Midwest Field Representative of Missions for the Progressive National Baptist Convention, Inc.
- Former President and Member of the South Holland Ministerial Association
- Former Off-campus Field Supervisor for Seminary Interns from McCormick Theological Seminary.
- Former Vice President of the Chicago Baptist Institute
- Former Trustee Board Member for Chicago Baptist Institute
- Former Treasurer for Chicago Baptist Institute
- Former Instructor at the Chicago Baptist Institute, “Introduction to Worship and Church Music”
- A lifetime-honored member of Lexington’s Who’s Who because of his demonstrated leadership and achievements.
- Authored his first book, “TAKE NO THOUGHT,” published in August 2013
Dr. Winfrey is passionate about Christian Education. He frequently responds to the requests to present workshops and seminars in Christian Education and Music and as guest speaker at churches locally and across the country. As an accomplished musician he exhibits his talents at the console of the organ, on piano and keyboard.
Pastor Winfrey’s theme is, and has been, “For I am not ashamed of the gospel of Christ: for it is the power of God unto salvation to everyone that believeth; to the Jew first, and also to the Greek.” Romans 1:16
"Ladies First" - Play & Reception
Culmination Weekend!
🎷 You're Invited! 🎤
Join us for an unforgettable evening of laughter, music, and heartfelt celebration at our Jazz & Roast event honoring the legacy of Dr. Preston R. Winfrey.
🗓 Friday, November 14, 2025
🕡 6:30 PM
📍 Pioneer Missionary Baptist Church
315 E. 161st Place, South Holland, IL 60473
This elegant evening will feature live jazz entertainment and a lighthearted roast in tribute to Dr. Winfrey’s years of service and leadership. Come ready to celebrate with joy and style!
Contributions appreciated
Join us for the culminating weekend celebration featuring a special play and luncheon in honor of our First Lady, Dr. Gloria Winfrey.
A Celebration of Service, Leadership And Love. You're invited to join us as we thank God for blessing us with a powerful leader in Dr. Winfrey for so many years. We will conclude the celebration with a special 3:00 PM service honoring his former students and children in the ministry. Light refreshments will be served
Hotel Suggestions For Your Stay!
Welcome to the Holiday Inn Express Hammond, IN. The Formula Blue concept features public space that is upbeat, dynamic, and friendly and provides flexible seating areas and furnishings that accommodate a wide range of needs and functions simultaneously. Our guest rooms offer a fresh, clean, and contemporary space that allow guests to be productive during their stay and have a great night's sleep. Click the link to book - Hotel in Hammond, Indiana | Holiday Inn Express & Suites Hammond
Frequently Asked Questions
Please reach us at www.prw44gala@gmail.com if you cannot find an answer to your question.
The gala will take place on Saturday, October 18, 2025, at 5:00 PM CST. The Venue will be at the Apostolic Banquest Center - 6320 S. Dorchester Avenue, Chicago, Illinois 60637
Shades of purple, silver and cream.
Yes. The attire is formal. Guests are encouraged to dress in elegant evening wear.
Tickets are available through the pay link on the website. Your tickets will be mailed to your address 45 days prior to the Gala.
Yes. Reserved tables are available for sponsors and groups of 8 or more. Please click the pay link within the website
Yes. We are offering space in the Commemorative Ad Book. You can purchase a full-page, half-page, or congratulatory message. Please click the link for the ad book to purchase your choice of an ad.
Sponsorship opportunities are available at various levels (Platinum, Gold, Silver, and Individual). Each level includes special recognition and benefits. Please click the appropriate link to purchase the sponsorship of your choice
Yes. A full-course dinner will be served during the evening celebration. Please let us know of any food allergies so you may have proper accommodations.
Yes, Pastor Winfrey celebration is open to all. There is a special discounted price for the child's ticket. Please look at the appropriate pricing link for the discounted price.
Absolutely! You can place a message in the ad book or contribute as an individual sponsor to honor Dr. Winfrey’s legacy.
Please email prw44gala@gmail.com for all event-related inquiries.
Countdown to Ladies First Play & Reception
The date is approaching fast and we’re making preparations. Don’t miss out on any of the events!
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