Darren Bailey Children: His Family Farm, Marriage to Cindy Bailey and Personal Life

Illinois Republican politician Darren Bailey has frequently spoken about the importance of family throughout his political career. However, his family faced an unimaginable tragedy when his son Zachary Bailey, daughter-in-law Kelsey and two grandchildren were killed in a helicopter crash in Montana. The incident brought national attention to Bailey’s children and the close relationships within his farming family.

Darren Bailey and his wife, Cindy Stortzum Bailey, have four children, three sons and one daughter. Their children were raised in southern Illinois, where the family operates an agricultural business and has longstanding connections to Christian education. Although Bailey has discussed his children and grandchildren during political campaigns, most members of his family have maintained relatively private lives.

How Many Children Does Darren Bailey Have?

Darren Bailey is the father of four children, consisting of three sons and one daughter. He shares all four with his longtime wife, Cindy Bailey.

The couple raised their children near Louisville, Illinois, where the Bailey family has operated a farm for generations. Their household was closely connected to agricultural work, religious activities and community involvement.

All four children married and established families of their own. By October 2025, Darren and Cindy had 13 grandchildren.

One of their sons, Zachary Bailey, worked in the family agricultural business before his passing in 2025. His death, along with those of his wife and two children, became one of the most difficult experiences in the family’s history.

Who Was Darren Bailey’s Son Zachary Bailey?

Zachary Bailey was one of Darren and Cindy Bailey’s three sons. He was 37 years old when he died in October 2025.

He grew up in southern Illinois and became involved in the family’s farming operations. As a fourth-generation farmer, Zachary helped continue the agricultural traditions established by earlier generations.

He was also an experienced helicopter pilot who used his aviation skills in connection with agricultural work.

Zachary had previously participated in Christian humanitarian activities involving the transportation of food and medical supplies.

He married Kelsey Bailey, and the couple established their home in the Xenia area of Illinois.

Together, they raised three children named Vada Rose, Finn and Samuel.

Zachary’s professional and personal life reflected the family’s longstanding emphasis on agriculture, faith and community involvement.

What Happened to Zachary Bailey and His Family?

On October 22, 2025, Zachary Bailey was piloting a helicopter in southeastern Montana when the aircraft crashed near Ekalaka in Carter County.

Zachary, 37, was killed along with his wife, Kelsey, 35, and their children Vada Rose, 12, and Samuel, 7.

Their third child, Finn, who was 10 years old at the time, was not aboard the helicopter and survived.

The aircraft was identified as a Robinson R66 helicopter. Federal investigators began examining the circumstances surrounding the accident.

The tragedy occurred while Darren Bailey was campaigning for the Republican nomination for Illinois governor.

Following the accident, Bailey temporarily suspended campaign activities to focus on his family.

His campaign confirmed that Darren and Cindy were devastated and requested privacy as they grieved.

Political leaders from both major parties offered condolences, including Illinois Governor JB Pritzker, who had previously faced Bailey in the 2022 gubernatorial election.

Who Are Darren Bailey’s Other Three Children?

In addition to Zachary, Darren and Cindy Bailey have two other sons and one daughter.

The family has generally kept the names and personal details of these three children outside extensive national media coverage.

Public accounts have confirmed that all four Bailey children married and established families.

The surviving siblings remained closely connected to their parents and extended family following the helicopter tragedy.

According to accounts shared after the accident, members of the Bailey family lived near one another in southern Illinois.

Their close geographical connections reflected the importance of family relationships and agricultural traditions.

Although their father has been involved in state politics, the surviving children have largely avoided the public attention associated with political campaigns.

How Many Grandchildren Does Darren Bailey Have?

Darren and Cindy Bailey had 13 grandchildren as of October 2025.

Their grandchildren have frequently been mentioned in Darren’s discussions about family values, education and the importance of protecting opportunities for younger generations.

Three of their grandchildren were born to Zachary and Kelsey Bailey.

Their daughter, Vada Rose, was 12 years old when she died in the Montana helicopter crash.

Their youngest son, Samuel, was seven.

Their surviving son, Finn, was 10 at the time of the accident.

Finn was traveling separately and was not aboard the aircraft.

Following the tragedy, relatives and community members rallied around the surviving child.

The Bailey family requested privacy while making arrangements and supporting one another.

Darren Bailey’s Children and the Family Farming Business

Darren Bailey is a third-generation farmer who grew up in Louisville, Illinois.

His family operates Bailey Family Farm, an agricultural business producing corn, soybeans and wheat.

The farm has remained an important part of the family’s identity for several generations.

Bailey began learning agricultural responsibilities during childhood and later continued working in the business as an adult.

His sons also became involved in farming operations, helping maintain the family’s agricultural traditions.

Zachary was particularly active in the business and contributed to its development before his passing.

The family’s farming background has influenced Darren’s political positions on agriculture, rural economic development and property rights.

He has frequently emphasized the importance of supporting family-owned farms and protecting rural communities.

Darren Bailey’s Wife Cindy and Their Family Values

Darren Bailey married Cindy Stortzum Bailey during the 1980s.

The couple built their life together in southern Illinois, raising four children while managing agricultural and community responsibilities.

Their Christian faith has remained an important part of their family identity.

In 2016, Darren and Cindy helped establish Full Armor Christian Academy, a private school offering education from preschool through high school.

The school was founded to provide families with an educational option centered on Christian teachings.

Both Darren and Cindy have participated in religious and educational activities within their community.

Following the loss of Zachary and his family, their religious beliefs became a significant source of comfort.

The couple received support from relatives, friends, church members and residents across Illinois.

How Family Life Influenced Darren Bailey’s Political Career

Darren Bailey began his political career after years of involvement in agriculture and local education.

He served on the North Clay Board of Education before winning election to the Illinois House of Representatives in 2018.

He later represented the 55th District in the Illinois Senate from 2021 to 2023.

In 2022, Bailey became the Republican nominee for Illinois governor but lost the general election to Democratic incumbent JB Pritzker.

He subsequently launched another campaign for governor in 2026.

Throughout his political career, Bailey has emphasized faith, family, farming and community as central principles.

His experiences raising four children and participating in the family business have influenced his views on education, agriculture and government policy.

The helicopter tragedy also revealed the strong support network surrounding his family.

Bailey temporarily stepped away from campaigning before returning to public activities after discussing the decision with his wife and relatives.

Darren Bailey Children and Family Background

Darren Bailey and his wife, Cindy, raised four children, three sons and one daughter, in southern Illinois.

Their family has longstanding connections to agriculture, Christian education and community service.

One of their sons, Zachary Bailey, died in October 2025 alongside his wife, Kelsey, and two of their children in a helicopter crash in Montana.

Their surviving grandson, Finn, was not aboard the aircraft.

Although Bailey’s political career has placed him in the public spotlight, his surviving children have generally maintained private lives.

His family remains an important part of his personal identity, reflecting generations of farming traditions and close community relationships.