The family around Mama June Shannon is facing another emotional turning point, as the widower of her late daughter Anna “Chickadee” Cardwell shares that his new fiancée is pregnant. The news lands in a tender spot for fans who watched Anna’s cancer battle and death, and who have seen Eldridge Toney grieve while staying close to the daughters Anna left behind. Now, he is stepping into fatherhood again, this time with fiancée Jessie English, and the mix of joy and lingering heartbreak is hard to miss.
The pregnancy marks a fresh chapter for a man who has spent the last two years trying to rebuild a life that was shattered when Anna died at 29. It is a reminder that even in a reality TV family known for chaos and punchlines, the storylines that stick are the ones about love, loss, and the messy work of moving forward.
The bittersweet baby news
Eldridge Toney, who was married to Anna Cardwell before her death from cancer in 2023, has confirmed that his fiancée, Jessie English, is expecting their first child together. The couple’s announcement framed the pregnancy as something they are “extremely excited” about, a clear sign that Eldridge is allowing himself to lean into happiness again after years defined by hospitals, treatments, and funerals, as detailed in coverage of Anna Cardwell’s widower. For Eldridge, who has already been a hands-on stepdad, the idea of welcoming a baby that he will raise from day one seems to signal a cautious but real sense of hope.
At the same time, the pregnancy is being described as a bittersweet development, because it arrives roughly two years after Anna’s death and in the shadow of a loss that still shapes the entire Shannon-Thompson clan. Reports note that Eldridge and Jessie are expecting their first child together while Jessie also brings a daughter from a previous relationship into the mix, underscoring that this is not a reset so much as an expansion of a blended family that already exists. The couple’s growing household, including Jessie’s child and Eldridge’s ongoing bond with Anna’s girls, is highlighted in updates that describe Jessie as pregnant with their while already parenting her own daughter.
From tragedy to a new chapter
The emotional weight behind this baby news only makes sense when set against the way Anna’s story ended. Anna Cardwell, the eldest daughter of Mama June Shannon, died at 29 after a fight with stage 4 adrenal carcinoma, a diagnosis that was publicly acknowledged by the family as terminal. Her mother, who shared the loss with fans on Instagram, described how Anna’s death hit the family, noting that her daughter was only 29 and that the grief has been a daily struggle. That raw reality has framed every update about Eldridge since, because his identity in the public eye is tied to being the man who stood by Anna through her illness.
In the months after Anna’s passing, Eldridge was often mentioned in the same breath as the family’s grief, with Mama June herself acknowledging how hard it has been to move forward while still honoring Anna’s memory. Coverage of the family’s reality series has emphasized that June and her relatives have been trying to heal from the loss, with The New Season of their show centering on how June and Anna Cardwell’s loved ones are coping after she lost her battle with cancer. Within that context, Eldridge’s decision to get engaged again and prepare for a new baby reads less like a sudden pivot and more like the next step in a long, painful process of rebuilding.
Who is fiancée Jessie English?
For viewers who mainly know Eldridge from his time with Anna, Jessie English is still a relatively new face, but recent reporting has started to fill in the picture. She and Eldridge got engaged in December 2025, a milestone that came after they had already begun blending their lives and families. The engagement, which was described as part of a bittersweet update, signaled that Eldridge was ready to publicly commit to a future that did not include Anna physically, even as he continues to carry her memory.
Jessie is not entering this relationship as a blank slate. She already has a daughter from a previous relationship, a detail that has been highlighted in coverage of the couple’s pregnancy announcement. That means the baby she is expecting with Eldridge will join a household that already includes her own child, as well as Eldridge’s emotional ties to Anna’s daughters. Reports describing Eldridge as Widower Eldridge Toney a baby with his fiancée make it clear that Jessie is stepping into a complex family tree, one that stretches from her own daughter to the kids Eldridge helped raise with Anna.
Staying close to Anna’s daughters
One of the most striking parts of Eldridge’s story is how committed he has remained to Anna’s daughters, even as he builds a new life. He has spoken about how his relationship with Kylee, who is 9, and her sister has been the main thing that has kept him going after Anna’s death. In an interview, he explained that staying present for the girls has given him purpose, especially in the months after Anna died from stage 4 adrenal carcinoma in December 2023, a loss detailed in coverage that notes how he has stayed close to Kylee and her sister.
That ongoing bond matters not just emotionally but practically, because Anna’s daughters are still very much part of the broader Shannon family orbit. Mama June and Alana “Honey Boo Boo” Thompson have spoken about how they are helping raise Anna’s daughter Kaitlyn and how they are processing the loss together, as seen when Mama June and on grieving Anna and their relationship with her daughters. Against that backdrop, Eldridge’s new baby will arrive in a family where the older kids are already navigating grief, reality TV cameras, and a constantly shifting set of adults trying to do right by them.
How the wider family is coping
The pregnancy news also lands at a time when the rest of the family is still very open about how hard it has been to move on from Anna’s death. Mama June has admitted that she struggles daily, even two years after losing her eldest child, and that the grief has reshaped how she parents her other daughters. Her comments about how the family has “accepted” that Anna was not going to go into remission, shared in a video where Dec footage captured the family talking about Anna’s stage 4 diagnosis, underline how long they have been living with the reality of her illness.
At the same time, the family’s shows have leaned into the idea that life has to keep moving, even when it feels impossible. The new episodes that focus on June and her relatives trying to heal from Anna’s death, as noted in The New Season coverage, show a clan that is still messy and loud but also more aware of how fragile everything is. In that sense, Eldridge and Jessie’s baby is not just a private milestone. It is another plotline in a family saga that has always played out in public, one that now includes a widower, a new fiancée, stepdaughters, and a child on the way.
More from Decluttering Mom: