Who Is Chelsea O'Donnell's Boyfriend? Inside Rosie O'Donnell's Daughter's Troubled Past Before Jail

Rosie O'Donnell's adopted daughter, Chelsea O'Donnell, is back in the headlines after she was sentenced to prison for violating her parole in a drug-related case, marking a new chapter in Rosie's ongoing family troubles. According to Page Six, a Wisconsin judge has officially cancelled Chelsea's probation on October 22, 2025, after she could not fulfil the designated Treatment Drug Court Program.

Further, the court documents reported that she showed 'minimal advancement' in her treatment. But it is not the first time that Chelsea has faced legal or personal troubles. Amid her recent arrest, learn more about her relationship crisis and drug-related offences.

Who is Chelsea O'Donnell's boyfriend? 

Chelsea O'Donnell's current relationship status is not publicly known. But her most notable past relationship was with Jacob Bourassa, her ex-boyfriend and father of three out of her four children. They reportedly began dating in 2018 amid her divorce from Nick Alligero. Chelsea went on to welcome three daughters, Skylar Rose, Riley and Avery Lynn. According to court filings by local outlets, Jacob obtained primary physical custody of his children in 2019 after they split up. 

Later, Chelsea O'Donnell welcomed a son with Jacob Nelund. But in 2024, she was again arrested following a domestic dispute with Jacob at their Wisconsin home. During this incident, the authorities found illicit substances and needles at their home. In the same year, she was arrested multiple times for drug-related cases, and her ex-boyfriend, Jacob Bourassa, sought to change the custody arrangement to cancel Chelsea's unsupervised visits. 

What does Rosie O'Donnell have to say about her adopted daughter?  

Chelsea O'Donnell's ongoing battles with addiction and the law have led to her current prison sentence. She has been arrested three times in 2024 with twice due to m**h-related charges and once for domestic issues. However, according to US Weekly, her failure to meet treatment conditions and new allegations resulted in the revocation of her release. Despite Chelsea and Rosie's strained bond, the comedian has expressed her heartbreak to the public.

During a previous interview with People and ET, Rosie admitted that despite their estrangement, she loved her deeply. At the same time, Rosie O'Donnell has prayed for "peace and recovery." Their sour bond further came to light when Chelsea filed to legally change her last name months ago and using her birth mother, Deanna Micoley's maiden name, Neuens. The decision reportedly came after she was cut from Rosie's will. Rosie, in turn, took to Instagram and asked for prayers on Instagram for Chelsea, sharing a picture of her before she suffered from addiction. In her words:

“I have compassion for those struggling with addiction. Chelsea was born into addiction and it has been a painful journey for her and her children we continue to love and support her through these horrible times. prayers welcomed.”

What do you think about the court's decision to revoke Chelsea O'Donnell's parole? 

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