The pair -- who officially separated in early April amid the coronavirus outbreak -- have been fighting in the courts over everything from custody agreements to marital funds and assets, and a lot of it has spilled out into the public sphere. So where did it all go wrong?
The couple tied the knot in June 2013 -- after first getting engaged in April 2011, calling it off three months later, and then recommitting to their engagement the following November. They also share three children -- 7-year-old son Camden, 5-year-old son Jaxon and 4-year-old daughter Saylor.
While their relationship has had its fair share of ups and downs, we're taking a look back at the time leading up to and since their split, and breaking down the legal battle brewing between the estranged pair.
Aug. 29, 2017 -- "Single Parent" Problems
In August 2017, Jay signed a one-year, $10 million deal to play for the Miami Dolphins, and Kristin revealed that she had no plans on uprooting the family and moving to Florida for the season. Kristin told ET's Katie Krause during a Facebook Live interview, "So, I'm a single parent for the next five months... It's a little chaotic, but in the best way." Kristin added that it "doesn't make sense to pack up the family just for five months."
"My kids are great," she added. "They're good kids for the most part. Of course we have our stuff, but it actually hasn't been as hard as I thought it was going to be, being a single parent. I have an amazing nanny, my mother-in-law is there with my kids right now, so I couldn't do it without them." Kristin also said that the kids were old enough that it was hard for their boys when Jay was working out of state. "They're old enough now, they get that Daddy's gone."
July 9, 2018 -- For Sale Signs Go Up
The couple decided to put their Nashville mansion up for sale, and they put it on the market for $7.9 million, six years after they bought it for $5.3 million. The lavish estate served as the backdrop for the first season of their reality show, Very Cavallari. During an episode that aired July 30, Jay and Kristin tour another mansion, which they end up moving into, and talk about their plans to stay there for the long haul.
As it turns out, they bought the new home back in April 2018 for a comparably reasonable $4.23 million, and this is the couple's "current marital residence" to which they frequently refer in their post-split court documents.
March 19, 2019 -- Role Reversal
While Kristin may have felt like a single mom after Jay signed with the Miami Dolphins in his 12th season with the NFL, the reality star said their parenting dynamic switched after Jay retired from playing football. With Kristin spending more time on her children's clothing and fashion line, Little James, she told ET's Katie Krause that they had "really completely shifted roles."
"So it's just been trying to navigate this new normal," Cavallari shared. "He's been great. I mean, obviously he's here with my three kids today, and you know, this is not the first thing he wants to be doing, so he's been great and I couldn't do it without him, truly."
"I think we make each other laugh," Kristin said of how they'd made their relationship work through the ups and downs of life. "I think that really can take you pretty far, and obviously trust is huge. We definitely have those two things, so that helps."
March 17, 2020 -- Vacation Complications
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being stuck on an empty island and forced to quarantine could be worse. thankful for my wolf pack during these scary times. this is where we are, this is us staying positive. we couldn’t be social here if we tried ✌🏼 i am afraid of what we will go home to when they let us back into the states 😢 hope you’re all staying safe where ever you happen to be ♥️
During a vacation to the Bahamas with Kristin, Jay and their three kids -- as well as Kristin's friend Justin Anderson and his fiancé, Austin Rhodes -- the group got stuck as a result of quarantine mandates over coronavirus concerns. They were all forced to stay in the Bahamas for several weeks. Kristin announced their return on April 6 in a series of posts she shared to her Instagram story.
April 7, 2020 -- Splitting in Secret
According to her divorce documents, filed later in the month, Kristin stated that the date of their official separation was April 7 -- one day after the group returned home to Nashville after their weekslong quarantine in the Bahamas. This date does not match up with Jay's divorce filing, which lists the date of their separation as several weeks later. It was subsequently revealed in court documents that the pair had actually begun discussing their split in March, before ever going on vacation with their kids.
April 21, 2020 -- Jay Files First
Jay filed for divorce April 21, citing "irreconcilable differences" as the cause. In his paperwork, Jay listed the couple's date of separation as April 21 as well. In his filing, Jay requested joint custody of their children and equitable distribution of the marital assets, stating that he has always been "the available at home parent and primary caretaker of the parties' minor children."
April 24, 2020 -- Kristin Hits Back
Three days after Jay filed for divorce, Kristin responded with her own divorce filing, citing both "irreconcilable differences" and "marital misconduct." She claimed in her legal docs that Cutler "is guilty of such inappropriate marital conduct as renders further cohabitation unsafe and improper," adding that "any misconduct alleged or implied against her in the complaint for divorce was in response to and/or as a result of misconduct on behalf of the Husband."
Kristin petitioned for primary physical custody of their children and requested child support. She also requested that Cutler be allowed visitation and that the former NFL star pay for their children's health insurance and maintain a life insurance policy with her name listed as the sole beneficiary. Kristin also denied her ex's claims regarding parenting roles in her filing, alleging that she has been "the primary residential parent" and that she is "a fit and proper person to be named Primary Residential Parent."
The court docs also revealed that a temporary restraining order was filed, which is said to be a standard in divorces in the state of Tennessee. The restraining order prevents Jay and Kristin from disposing of or concealing marital property, harassing each other or relocating the children.
As for the "marital misconduct" claim, ET spoke with Rachel Stockman, president of Law & Crime Network, for more information on what the term could mean from a legal standpoint. "At its face, you might assume that means affair or some kind of adultery, but under Tennessee law that is not necessarily the case. It basically means that she believes her husband has been treating her in some way unfairly and she can’t cohabitate with him anymore," Stockman said, adding that "inappropriate marital conduct" can refer to many things, ranging from infidelity or abuse to alcoholism.
April 26, 2020 -- Kristin Announces Their "Loving Conclusion"
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With great sadness, after 10 years together we have come to a loving conclusion to get a divorce. We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of. This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family.
Kristin took to Instagram to announce the news of their divorce with a sweet snapshot and a statement that painted the split in a positive and amicable light.
"With great sadness, after 10 years together we have come to a loving conclusion to get a divorce," she wrote. "We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of. This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family."
April 27, 2020 -- Custody Conflict
A day after Kristin announced their divorce, and their court docs went public, a source told ET that things had turned sour between the pair after Kristin requested primary custody in her filing.
"Kristin and Jay planned to keep everything amicable, but that's not the case anymore," ET's source said. "Kristin filing for primary physical custody upset Jay. He loves his children more than anything and thinks the couple should be reasonable and split custody… Kristin has made comments about possibly moving back to L.A., which is also a concern of Jay's, as home for the family is currently Nashville."
April 28, 2020 -- Living Apart
ET learned that the couple are no longer living together but instead are trading off, with each living there three days on, three days off, with their children. When not in the primary marital residence, Jay stays at their second house -- the Nashville mansion they put on the market in 2018 and have yet to sell -- while Kristin stays with a friend.
April 29, 2020 -- At War Over Money
In new court documents obtained by ET, Kristin said that Jay was trying to control their marital assets and was preventing her from buying her own home. In the docs, Kristin claimed that she and Cutler "have been experiencing problems in their marriage for the last several years," and in the fall of 2019, "Things were so bad in the marriage that [she] started looking for another home." After she found a place she liked, she "put a contract on the property, escrowed the funds," and Jay "never objected." However, she said she decided not to buy the house after she and her estranged husband "attempted to salvage the marriage… However, both parties realized the attempt to reconcile was not working and knew a divorce was inevitable."
Kristin said that, after they separated and began splitting their time with their kids in their home, Jay approached her with a settlement that she felt was "unfavorable," and she alleged that Jay then told her he was going to ask his attorney to tell their business manager not to release the funds she'd need to buy herself a new home. She further claimed that Jay said he'd only release the funds if she agreed to his parenting and custody plan. Furthermore, Kristin said she believes that her estranged husband "hurried to file his complaint as a way of punishing her."
For Kristin, one of her main concerns is the emotional well-being of their children, and she said she's afraid that if she and Jay are required to reside in the same home, it might create "an unhealthy environment causing irreparable harm" to their kids. She further claimed that Jay often "attempts to draw her into an argument" in front of their children, and she "fears the situation will escalate."
May 4, 2020 -- Peace Is Made
According to court documents obtained by ET, Kristin was "permitted to purchase" the home she was looking at in Franklin, Tennessee, and she and Jay also entered into a permanent parenting plan "that they attest is in the best interest of the minor children." The documents state that, until Kristin moves into the new home, "the parties shall continue to follow the week to week nesting plan that they have previously agreed to."
According to the parenting plan, Jay and Kristin will each have the kids every other week. The permanent parenting schedule took effect immediately. "The parties will continue this parenting schedule rotation and alternate parenting time with their children on a week-on, week-off basis," the documents state.
Meanwhile, a source told ET that the two want to work things out amicably for the sake of their children. "Jay and Kristin are doing better, as the couple has hammered out temporary custody for the time being and Kristin was able to buy the house she wanted in Nashville, not too far from their current house," the source said. "At the end of the day, Kristin and Jay want to make everything work for their children and they're still deciding what that looks like but know they need to remain a solid front."