Olen Underwood Obituary

Judge Olen Underwood, 82, passed away peacefully into the arms of his Savior on February 28, 2025.

Olen Ulesus Underwood was the rock of his family, a devoted father to four children and a beloved grandfather to thirteen. His steady presence, unwavering support, and deep care for those around him made him not only a cherished family man but also a loyal friend to many.

Judge Underwood dedicated over 40 years of his life to serving the State of Texas as a judge in Montgomery County. He was the first judge of the 284th District Court, presiding from 1981 to 2005. His wisdom and leadership earned him the trust of three Texas governors, who appointed him as the Presiding Judge of the Second Administrative Region, a role he held from 1996 to 2022. A highly respected figure in the legal community, he also served on numerous judicial and nonprofit boards, shaping the justice system with integrity and compassion.

His passion for justice extended beyond the courtroom. Judge Underwood was a tireless advocate for troubled and vulnerable youth. In 1993, he founded the Student Transition and Recovery (STAR) Program, a groundbreaking mentoring initiative aimed at preventing incarceration for middle school students-a program that has since expanded to multiple states. He was instrumental in bringing the CASA (Court Appointed Special Advocates) program to Montgomery County and served for nearly a decade as the Presiding Juvenile Judge in Conroe, working to change the trajectory of young lives. His service to the youth of Montgomery County was further recognized with the naming of the Olen Underwood Juvenile Justice Center.

Before his legal career, Olen was a gifted athlete. He played football for the University of Texas from 1961 to 1964, winning a National Championship with the Longhorns in 1963. His contributions to the team were later honored with his induction into the Longhorn Hall of Honor in 2003. Drafted by the New York Giants, he went on to play linebacker in the NFL and AFL from 1965 to 1971, with the New York Giants, Houston Oilers and Denver Broncos. In 1968, he was selected for the Pro Bowl. While playing for the Oilers, he also pursued his legal education, earning his law degree from the University of Houston Law Center in 1970. He practiced law in private practice before his appointment to the bench.

Beyond his professional achievements, Olen was a man of deep faith. He founded You Are My Sonshine Ministries, a retreat center dedicated to supporting pastors and the Christian community. His love for Christ was evident in all aspects of his life, and he lived by the words of Micah 6:8: "Do justice, love kindness, and walk humbly with your God."

A Celebration of Life service will be held on March 16, at 2:00 PM, at The Woodlands Bible Church, 995 Pinyon Pine Drive, The Woodlands, TX 77380. In lieu of flowers, donations can be made to You Are My Sonshine Ministries at 411 S. Rivershire Conroe, TX 77304, or at https://gofund.me/3f854b9b.

Judge Underwood's legacy is one of unwavering service, steadfast faith, and profound kindness. His impact will be felt for generations to come.

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Published by The Courier of Montgomery County from Mar. 13 to Mar. 14, 2025.

Memories and Condolences
for Olen Underwood

8 Entries

Lyn Ramsey

July 9, 2025

I am heartbroken to learn so late of Judge Underwood´s passing. I worked for him for a few years, assisting with his heavy workload...before the 11th region was created. He was such a joy to work with-a truly brilliant legal mind with a devilish sense of humor. He deeply appreciated his staff who all became like family and who all clearly adored him. I did too. He will be deeply missed.

John D, MacDonald II

July 6, 2025

Judge Underwood was an excellent judge and good man. I had many cases in his court and was always treated with respect. His work in Juvenile law untangled what had been an shameful mess. Rest in peace Judge.

David Walker

May 12, 2025

Judge Underwood was an excellent jurist and an extremely good man. I practiced in his court and worked with him for almost thirty years. I am privileged to have known this wonderful Christian man.
David Walker

Timothy Payne

April 5, 2025

When Barbara was running for District Clerk's, Judge Underwood shared with me the importance of having representatives of ypur candidate at the polls on election day.

Judi Horton

March 23, 2025

Rest in peace.

Ben Breedlove

March 18, 2025

My memories of Mr. Underwood are long ago, but what a mountain of a man, and what I remember most is his display of faith. The family is in my prayers during this difficult time and that Jesus' peace found in John 14 will engulf them as they recall great memories of Mr. Underwood.

Mel Brown

March 16, 2025

Judge Olen Underwood was a man who loved justice and loved youth. I was saddened to learn of his death.

Larry Foerster

March 13, 2025

Montgomery County has been blessed with many fine judges who have been faithful stewards of justice. Olen Underwood was one of the very best.
My friendship with Olen began in the spring of 1980 when we were both running in the Democrat primary -- Olen for the vacant 2nd 9th District Court and me for Montgomery County Attorney. At that time there were no Republican office holders in Montgomery County and few across the state.
Olen made an imposing candidate with his stature as a former NFL football linebacker. But I quickly learned that his character was even more impressive. He was humble, good humored and devout. He made no effort to hide that he loved his Lord Jesus first, followed closely by his family and his community. He lost his race to John Martin (another good man). But God had better plans for Olen.
In the spring of 1981, Republican Govenor Clements appointed him to the new 284th District Court. For the next 6 terms, Olen had no opponent as he was highly regarded for his fairness, sound judgment and hard work. It was always a pleasure to stand before his bench. He never played favorites; he treated both the lawyers and the litigants in his courtroom with respect.
A short time after being appointed to the bench, Olen started the County Dispute Resolution program as he felt the need to move the backlog of cases and reduce the costs to the litigants by offering mediation as an option. Now it is required by all courts. Olen recruited me to serve on the new board of directors; it was hard to say "NO" to Olen Underwood.
Olen also initiated a morning prayer group of local lawyers. He always was humble and willingly shared his personal feelings with each of us. I also became acquainted with his heart for Christian ministers, as he offered his San Saba ranch as a weekend retreat for them to rest and recharge. He was a gracious host who cooked their meals and attended to their needs while they were there.
Olen Underwood was one of the finest Christian men I have known, and I was honored to call him my friend for 45 years. May God bless Barbara and all of Olen's children and grandchildren. He has left an enduring legacy in the judicial community that will last for generations to come.

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