Jay Cutler: NFL Career, Diabetes Diagnosis, and New Engagement

Jay Cutler has packed a lot of life into 41 years: a decade under center in the NFL, a very public marriage and divorce, a diabetes diagnosis that could have ended his career, and now an engagement to a new partner. This article walks through the key chapters—the stats, the relationships, and the health journey—with the facts and sources to back them up.

Born: April 29, 1983 · NFL Career: 2006–2017 (12 seasons) · Passing Yards: 35,133 · Touchdowns: 227 · Interceptions: 160 · Diagnosis: Type 1 diabetes (2008)

Ten key facts at a glance, from his college days to his health condition:

Why did Kristin leave Jay Cutler?

Kristin Cavallari’s public statements

In April 2020, Kristin Cavallari announced via Instagram that she and Cutler were divorcing after seven years of marriage. The joint statement read: “With great sadness, after 10 years together we have come to a loving conclusion to get a divorce.” (Good Morning America). Cavallari later said on a podcast that the split was due to “irreconcilable differences,” without going into specifics.

Jay Cutler’s allegations of lying

Cutler, in his own divorce filing, cited irreconcilable differences and also accused Cavallari of lying about financial matters, as reported by Nicki Swift. He described himself as the primary caretaker of their three children and requested joint custody. The conflicting statements mean the public has never gotten a single, agreed-upon reason for the divorce.

Divorce timeline and custody

Cavallari filed her own response citing “marital misconduct and irreconcilable differences.” The couple reached a temporary custody agreement in May 2020 to split time with their children Camden, Jaxon, and Saylor. The divorce was finalized in 2022, but the exact terms remain private.

The implication: Without a definitive public disclosure from both sides, the motives behind the split remain the subject of speculation rather than confirmed fact.

Who is Jay Cutler’s new relationship?

Identity of the new partner

Jay Cutler is now engaged to Samantha Robertson, a woman he has been dating since after the divorce was finalized. The relationship became public in September 2023 when Robertson posted a photo of the two in Montana with the caption “Sunsets in Montana never disappoint 🫶,” as People reported. Cutler later made the relationship Instagram-official.

Engagement announcement in 2023

In November 2024, multiple sources confirmed to People that Cutler and Robertson are engaged. The couple attended the Yellowstone season 5B premiere together on November 7, 2024, appearing as a pair.

How the relationship became public

Robertson’s September 2023 Instagram post was the first public sign. Cutler himself has been relatively private about the relationship, but the engagement news broke through insider reports rather than a formal announcement from the couple.

Why this matters: This new chapter signals a clear move forward from Cutler after the high-profile divorce, and publicly cements his personal life beyond football.

When was Jay Cutler diagnosed?

Year of diagnosis

Cutler was diagnosed with type 1 diabetes in 2008, during his second NFL season with the Denver Broncos.

Circumstances of discovery

The diagnosis came after Cutler felt ill during training camp. He lost weight, was constantly thirsty, and struggled to keep energy levels up—a classic onset. After blood tests confirmed the condition, he began immediately managing it with insulin.

Impact on his NFL career

Despite the diagnosis, Cutler continued to play quarterback at the highest level. He never missed a game due to diabetes, and his career stats—35,133 passing yards and 227 touchdowns—show his resilience. He has credited his medical team and modern diabetes devices for allowing him to keep playing. He uses an insulin pump and continuous glucose monitor to manage blood sugar levels.

The takeaway: The diagnosis did not end his career; it forced a new level of discipline that arguably made him more organized off the field.

What is Jay Cutler’s diagnosis?

Type 1 diabetes explained

Type 1 diabetes is an autoimmune condition where the pancreas produces little or no insulin. Cutler has been open about using an insulin pump and continuous glucose monitoring to keep his blood glucose levels stable throughout games and practices.

Symptoms and management

Common symptoms include excessive thirst, frequent urination, fatigue, and blurred vision—all of which Cutler experienced. His management routine now involves checking glucose levels multiple times a day and adjusting insulin doses, especially around high physical exertion.

Advocacy work

In 2015, he founded the Jay Cutler Foundation to increase awareness and support for type 1 diabetes research and education. The foundation has worked with schools and hospitals to spread knowledge about the condition.

The pattern: Cutler’s public advocacy gives a human face to a disease that affects millions, and shows how elite athletes can thrive with it.

Did Kristin Cavallari get money from Jay Cutler?

Alimony and child support

Divorce settlement details are not fully public, but it is known that Cavallari received child support and assets as part of the split. Cutler’s financial disclosures from the divorce proceedings indicated he pays for the children’s expenses.

Dispute over assets

Cutler accused Cavallari of lying about financial matters, but no formal court documents detailing asset division have been made public. Both parties have kept the specifics close to their chests.

Public claims of lying

In an interview, Cutler suggested that Cavallari was not entirely truthful about certain financial issues, though he did not elaborate. These allegations are reported by Nicki Swift but remain unverified in court.

The trade-off: The lack of full transparency means fans and media can only piece together clues, while the couple appears to have reached a private agreement to move on.

The seven years since Cutler’s last NFL snap have been as eventful as his playing days. For a former quarterback who learned to manage a chronic disease in the national spotlight, the next chapter—marriage to Robertson and continued parenting—will test whether the discipline that defined his career can also define his personal life. For fans wondering, the clear lesson is: Cutler continues to make headlines off the field, and his diabetes advocacy remains a growing part of his legacy.

For another athlete balancing a professional sports career with type 1 diabetes, Jordan Thompsons diabetes journey offers a compelling parallel.

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