Winfrey Retirement Gala

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Winfrey Retirement Gala

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    Celebrating a Lifetime of Achievements

    Celebrating a Lifetime of AchievementsCelebrating a Lifetime of AchievementsCelebrating a Lifetime of Achievements

    Celebrating a Lifetime of Achievements

    Celebrating a Lifetime of AchievementsCelebrating a Lifetime of AchievementsCelebrating a Lifetime of Achievements

    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

    A Message from Dr. Winfrey

    Celebrate Unforgettable Moments of the Retirement Gala

    Join us as we honor Pastor Dr. Preston R. Winfrey for an extraordinary 44 years of faithful service to the ministry and community. Celebrate this remarkable legacy at The Regal Retirement Gala, an elegant evening of gratitude, fellowship, and celebration. We invite you to an unforgettable night of reflection, honor, and joy as we pay tribute to a lifetime of dedication and leadership.

     A Legacy Worth Honoring

    For over four decades, Dr. Preston R. Winfrey has served with unwavering faith, visionary leadership, and a heart committed to God's people. As we prepare to celebrate his retirement and 44 years of ministry, we invite you to become part of this historic moment by becoming a sponsor. Your sponsorship is more than a donation — it is a statement of support for a life devoted to service, leadership, and community transformation. Whether through a Platinum, Gold, or Silver Sponsorship, or by choosing an exclusive sponsorship, your contribution will help make this celebration truly unforgettable. Individual sponsors will receive special recognition for their generosity and presence — seated at VIP tables and honored in our promotional materials. Your gift will uplift a legacy and inspire the next generation of ministry and service. This is not just a gala, it is a testimony and a celebration of faith. And most importantly a tribute to a servant leader whose impact will echo for generations. Will you help us honor this extraordinary journey? 

    For over four decades, Dr. Preston R. Winfrey has faithfully served the Pioneer Baptist Church with unwavering dedication, wisdom, and love. As we commemorate his 44 years of impactful leadership and celebrate his well-deserved retirement, we invite you to be part of this historic moment.


    Place a congratulatory message in our 44th Anniversary & Retirement Souvenir Book—a timeless keepsake that will honor Dr. Winfrey’s legacy and the countless lives he has touched.


    Whether you share words of gratitude, cherished memories, or a note of encouragement, your message will become part of a beautiful tribute to a remarkable journey of faith and service.

    Spread the Gospel: A Tribute to Dr. Preston R. Winfrey
    Where: Pioneer Baptist Church

    Beginning July 20, Pioneer Baptist Church will host a series of monthly services featuring guest preachers in honor of Dr. Preston R. Winfrey’s exemplary service to the ministry. 

    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 a heartfelt afternoon honoring our beloved First Lady, Dr. Gloria Winfrey, during the culmination weekend of her retirement celebration. This special event features an inspiring theatrical performance followed by an elegant brunch, reflecting her years of service, strength, and compassion.

    📅 Saturday, November 15, 2025
    🕑 2:00 PM
    📍 Pioneer Baptist Church
    315 E. 161st Place, South Holland, IL 60473
    💜 Admission: $20 (includes hor d'oeuvres and the play)

    Let us gather in love, laughter, and appreciation as we honor a woman of faith, dignity, and purpose.

     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  

    Retirement Gala - Adult Ticket

    Commemorative AD Book - Full Page

    Retirement Gala - Child's Ticket

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase Ticket - Adult

    Retirement Gala - Child's Ticket

    Commemorative AD Book - Full Page

    Retirement Gala - Child's Ticket

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. Please be advised a convenience fee will be added to the total cost. This fee covers the payment pr

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, you may submit payment with a money order.

    Purchase Ticket - Child

    Commemorative AD Book - Full Page

    Commemorative AD Book - Full Page

    Commemorative AD Book - Full Page

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase A Full-Page AD

    Commemorative Ad Book - Half Page

    Commemorative Ad - Inside Back Cover

    Commemorative AD Book - Full Page

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase A Half Page AD

    Commemorative Ad - Inside Front

    Commemorative Ad - Inside Back Cover

    Commemorative Ad - Inside Back Cover

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase Inside Front Cover AD

    Commemorative Ad - Inside Back Cover

    Commemorative Ad - Inside Back Cover

    Commemorative Ad - Inside Back Cover

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. .

    Purchase Inside Back Cover Ad

    Commemorative Ad - Back Cover

    Commemorative Ad - Back Cover

    Commemorative Ad - Back Cover

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase Back Cover AD

    Platinum Package

    Commemorative Ad - Back Cover

    Commemorative Ad - Back Cover

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase Sponsorship Package - Platinum

    Gold Sponsorship Package

    Commemorative Ad - Back Cover

    Silver Sponsorship Package

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase Sponsorship Package - Gold

    Silver Sponsorship Package

    Silver Sponsorship Package

    Silver Sponsorship Package

    Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order. 

    Purchase Sponsorship Package - Silver

    Play & Reception

    Silver Sponsorship Package

    Play & Reception

    Join us for the culminating weekend celebration featuring a special play and luncheon in honor of our First Lady, Dr. Gloria Winfrey. Please click the link below to reserve your seat today!  Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card trans

    Join us for the culminating weekend celebration featuring a special play and luncheon in honor of our First Lady, Dr. Gloria Winfrey. Please click the link below to reserve your seat today!  Please be advised a convenience fee will be added to the total cost. This fee covers the payment processing charges associated with credit card transactions. To avoid this fee, please contact the church to submit payment with a money order.  

    Purchase Tickets to Play and Brunch

    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. Venue details will be announced soon. 

    Yes. The attire is formal. Guests are encouraged to dress in elegant evening wear. 

    Tickets are available through the pay link in the website. 

    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. 

    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 Retirement Gala!

    The date is approaching fast and we’re making preparations. Don’t miss out on any of the events!

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