Samantha Robertson is a name that gained attention in recent months due to her relationship with former NFL star Jay Cutler, but she has her own background and achievements outside of the spotlight of her personal life. In this article, we will take a closer look at her career, personal life, and what has made her a public figure.
Early Life and Background
Samantha Robertson was born and raised in the United States. While not much has been revealed about her early life or education, it is clear that she is a private individual who values her personal life. She is known for being active on social media, where she shares aspects of her life, including her travels and family moments.
Career Path
Although Robertson’s career hasn’t been as widely publicized as some other figures, she has been involved in various entrepreneurial and social media endeavors. Here’s a general outline of her career journey:
- Entrepreneurship and Business Ventures: Samantha Robertson has built a career through entrepreneurial ventures. While specifics about her businesses are scarce, she appears to focus on lifestyle, fashion, and beauty-based initiatives. She often shares updates on her Instagram, where she engages with followers about products, brands, and services that she supports.
- Social Media Presence: Over the years, Robertson has gained attention through her strong presence on social media platforms, particularly Instagram, where she frequently posts about her travels, lifestyle, and family life. Her curated posts, often showcasing beautiful scenic locations and personal moments, have attracted a following. Robertson often engages in brand partnerships and collaborations, using her platform to promote various products.
- Mom and Family-Oriented Content: As a mother, Samantha also frequently shares glimpses of her life with her two daughters, Sophia and River, whom she shares with her ex-husband, Trace Ayala. Her content revolves around motherhood and family life, and she is often seen spending time with her children.
Personal Life: A High-Profile Relationship with Jay Cutler

Samantha Robertson rose to more prominent public attention after starting a relationship with Jay Cutler, the former Chicago Bears quarterback. Here’s a breakdown of the key moments in their relationship:
- Public Relationship Beginnings: The couple went Instagram official in September 2023, posting a heartfelt picture together in front of a sunset in Montana. The caption read: “Sunsets in Montana never disappoint 🫶,” signaling their deep connection and shared joy.
- Engagement Announcement: Robertson and Cutler’s relationship took another step forward when they got engaged. The engagement was confirmed in November 2023 when Robertson appeared at the premiere of Yellowstone Season 5B wearing an engagement ring. Sources close to the couple exclusively confirmed their engagement to PEOPLE. This announcement excited many fans and followers of both individuals, as they had already gained attention for their beautiful moments shared on social media.
- Past Relationships and Family: Prior to her relationship with Cutler, Robertson was married to Trace Ayala, an actor, though details of their relationship timeline remain unclear. Together, they share two daughters, Sophia and River, who occasionally appear on her Instagram. In addition to her romantic relationship with Cutler, Robertson maintains an active role as a mother and is often seen spending time with her daughters.
Jay Cutler and Kristin Cavallari’s Past Relationship
Before Samantha Robertson, Jay Cutler was famously married to reality TV star Kristin Cavallari. The two were married in 2013 and had three children together—Camden (12), Jaxon (10), and Saylor (8). They separated in 2020 after seven years of marriage.
Kristin Cavallari has expressed in interviews that she hopes her ex-husband finds happiness and remarries, stating, “I want him happy… My kids benefit from that.” Despite their divorce, Cavallari and Cutler co-parent their children and maintain a respectful relationship for the sake of their family.
Future Plans and What’s Next for Samantha Robertson?

As Samantha Robertson steps into this new chapter of her life, her engagement to Jay Cutler marks a fresh and exciting turn. She has yet to announce any specific career plans related to her engagement, but it’s clear that her life is about to become more public with her relationship gaining increasing media attention.
Robertson may continue to grow her social media presence, pursue new business ventures, and enjoy her family life. It’s likely we’ll see her balancing her roles as a mother, entrepreneur, and fiancé in the public eye in the coming years.
Conclusion: Samantha Robertson’s Journey So Far
Samantha Robertson has managed to build a life that blends entrepreneurship, family, and love. While her career and personal life may not always be in the limelight, her relationship with Jay Cutler has certainly placed her in the public’s eye. As they begin their journey together, it will be interesting to see how she navigates her growing presence in the media while continuing to be a dedicated mother and entrepreneur.
Fans and followers are eager to watch how her career and family life evolve, and with the support of her growing following, Samantha Robertson is on her way to making an even bigger impact in the future.
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