Inside Madonna and Guy Ritchie's Custody Battle: An in-Depth Look at Why Rocco Left His Mom, What Has Been Resolved – and What's Next

Rocco "has a huge amount of sway" in his future living situation, a legal expert tells PEOPLE

Photo: Steve Granitz/WireImage; David Fisher/REX/Shutterstock

Madonna and Guy Ritchie have been “Hung Up” in and out of court in a transatlantic custody squabble over their 15-year-old son Rocco.

On Monday, a London judge ruled that the pop star, 57, can withdraw her previously filed legal proceedings in the U.K., so the custody battle will remain under U.S. jurisdiction in the New York Supreme Court.

The exes’ ongoing fight over their son’s living situation began in December and has prompted judges involved in both London and New York to urge Madonna and Ritchie, 47, to settle the dispute as soon as possible for Rocco’s benefit.

As their lawyers work toward a private agreement, Rocco “has a huge amount of sway … given his age, far more than, say, a child under 12 years old, and even more, his parents can’t decide,” Michael Stutman – head of the family group at Mischon de Reya New York and a family law expert who is familiar with but not involved in the high-profile case – tells PEOPLE.

So, while another hearing is tentatively scheduled for June 1 in New York, Madonna and Ritchie’s lawyers and Rocco’s court-appointed attorney will continue to try to hash out a settlement out of court.

“It is their lawyers’ role to get their clients what they want. They guide those wants to fall in line with what’s reasonably possible so everyone walks away with something. If they fail to do that, forcing a judge to make the final decision is a gamble between the best-case scenario and the worst-case scenario: Neither Madonna nor Guy Ritchie may be happy with that outcome,” Stutman explains.

“Aside from that, they will be encouraging their clients to align and become united as this will not be the first time Rocco or any teenager will change his mind and run all over. By coming together they can focus on what’s really important: parenting their child instead of letting their child run the show,” Stutman adds.

While Rocco’s future living situation remains unresolved, here is an in-depth look at his parents’ high-profile custody war.

Dec. 1 – 2, 2015: Madonna plays back-to-back shows at London’s O2 Arena.

Rocco had been traveling with his mom on her Rebel Heart Tour for a string of dates, keeping up on his schoolwork with a tutor.

Her son performed with her dancers on her MDNA Tour in 2012. (“She’s a good mother … She’s very strict strict but in a good way,” he told Ellen DeGeneres the same year.)

But last summer, the pop veteran told Entertainment Weekly guest editor Andy Cohen: “I think he’s probably gonna work behind the scenes … He s not interested in performing on stage with me right now. There’s way cooler things. Your mom is not that cool when you’re 14.”

Dec. 23, 2015: Madonna appears at a New York Supreme Court hearing, where it was revealed Rocco had been living with his father in the U.K. and had expressed his desire to continue living abroad.

Ritchie was not present at the hearing, and it was later revealed he was offered the option to phone in to hear the proceedings but declined.

Justice Deborah Kaplan ordered that the teen be returned to the U.S. by the next month, reportedly saying: “If he wants to stay with his father, he must return to his mother.”

In January, a Ritchie source told PEOPLE Rocco left his mom, an “old-school parent,” in an act of rebellion because he got bored with touring and preferred living with his more laid-back father, splitting time between London and their Ashcombe estate, where Rocco likes to run around with a Nerf gun.

And later in January, a source told PEOPLE Ritchie “wants Rocco to have the confidence he lacked growing up and thinks Madonna’s stern parental style is counterproductive … The welfare of Rocco is Guy’s priority.”

Dec. 24, 2016: Madonna reportedly files legal proceedings in London under the Hague Convention on International Child Abduction, alleging Rocco had been illegally retained in the U.K. after visiting his dad.

Dec. 25, 2016: Madonna celebrates Christmas in New York without Rocco.

The singer posted photos of her family festivities – with daughter Lourdes, 19, son David, 10, and daughter Mercy, 10 – to her Instagram. Rocco’s absence was noticeable in her feed, as she posted a throwback shot of her oldest son, captioning it: “Merry X-mas to the Sun-shine of my Life.”

Dec. 31, 2015: As a source told PEOPLE, Rocco spends New Year’s Eve as he did Christmas the week before: with his father and stepmom Jacqui Ainsley, 34.

Jan. 6, 2016: A new term has started in New York, but Rocco has yet to return to school in the U.S.; Madonna returns to the road, picking up her tour in Mexico City.

“He should have been home already,” a source close to the singer said at the time, alleging Rocco had missed some school. “Madonna is a devoted mother, and a big priority is her children’s education.”

Jan. 9, 2016: Madonna defends her work-life balance as a single mother before she attends her ex’s charity gala with her youngest children.

Madonna walked the red carpet with kids David and Mercy and posed for pictures with ex-husband Sean Penn at his Help Haiti Home fundraiser in Beverly Hills.

“Its possible to be an entertainer and a good mother … Too bad we don’t live in a society where many encourage strong independent single working moms!” she captioned a throwback photo with her kids on Instagram earlier in the day.

The day before, PEOPLE reported that a friend of the former couple said, “She is going to fight, fight, fight, and she is going to fight to the end.”

Jan. 18, 2016: Madonna vents about custody battle onstage.

While performing in Nashville, a fan proposed to her, and she said, “I’m looking for a husband, not a c— … I already married a c—.” (As she was on good terms with ex Penn at his charity gala that same month, she was seemingly calling out her other former spouse, Ritchie.)

Feb. 3, 2016: Madonna and Ritchie’s lawyers are originally due in court for a second custody hearing, but it is postponed until March 2.

At the time, a Ritchie source told PEOPLE Madonna flew to London the weekend before: “She was hoping to persuade Rocco to come back to New York … but Rocco reiterated his determination to stay in London … It was a series of short, difficult conversations between Madonna and Rocco.”

Feb. 6, 2016: Rocco is photographed in London smoking suspicious-looking cigarettes.

The Sun posted photos of Rocco smoking with friends in a public area.

“This is exactly what Madonna has been afraid of,” a source told PEOPLE at the time. “Rocco still isn’t back in school – and now this. He is just a rebellious teenager, but he needs guidance and direction from his father.”

Stutman says Rocco’s antics under his father’s care won’t bode well for his father’s case – but Madonna making headlines won’t do her any favors, either.

“In terms of a judge’s concern over a parent’s ability to discipline a child and/or protect a teenager from themselves, none of these events speak all that highly of Mr. Ritchie and his abilities,” Stutman said.

“However, given Madonna’s recently reported behavior she is demonstrating that discipline is not a strong suit, and it then becomes a question of choosing between the lesser of two evils.”

Feb. 29, 2016: Rocco is photographed with a broken wrist after shaving his head.

March 2, 2016: Madonna and Ritchie’s lawyers attend a New York hearing, where they, Rocco’s court-appointed attorney and Justice Kaplan agree Rocco will remain in London for the time being as his parents work toward a custody settlement in private.

Madonna (in New Zealand on tour) and Ritchie (in the U.K.) called into the hearing, where it was revealed Rocco – whose lawyer described the public custody battle as “stressful” on him – is attending a school chosen by both parents.

Madonna’s lawyer, Eleanor Alter, also noted that the singer decided not to enforce Justice Kaplan’s order for Rocco to be returned to the U.S. – but that they felt Ritchie “taught his son that obeying court orders … is not necessarily important. That is one of the most serious things that has happened in this court.”

All three parties’ attorneys also disclosed that they had nearly reached a custody agreement before the hearing but that it had fallen apart in the eleventh hour.

March 3, 2016: Ritchie attends a hearing in London, where Madonna’s U.K. attorney argued to withdraw her legal proceedings in the U.K. to focus on litigation in the U.S.

High Court Judge Alistair MacDonald urged the contentious exes to reach an “amicable settlement” to the “highly unfortunate and deeply regrettable” dispute, The Guardian reported.

March 5, 2016: Madonna dedicates song to Rocco in concert.

“There’s no love stronger than a mother for her son, and if I talk about him too much, I’m going to cry,” she told the Auckland, New Zealand, crowd, dedicating her performance of “La Vie en Rose” to Rocco. “I hope he hears this somewhere and he knows how much I miss him.”

Later that week at a Melbourne, Australia, show, she dedicated another song, “Intervention,” (sample lyric: “I know that love will keep us together / I know the road looks lonely”) to the teen.

March 10, 2016: Ritchie, wife Ainsley and Rocco appear in court in London, where Judge MacDonald ordered that all arguments be private per restricted reporting conditions.

March 20, 2016: Madonna’s Rebel Heart Tour wraps in Sydney.

Just days before, the singer accidentally exposed a concertgoer’s breast onstage. While the wardrobe malfunction had the Internet buzzing, the fan forgave the incident, reportedly saying: “I didn’t realize my boob was such a big deal … Why would I sue Madonna for the best moment of life?”

Despite tabloid reports that she had been suffering a custody battle-caused meltdown on her final leg of the tour, Madonna slammed the accusations, writing on Instagram: “Too bad people don’t know the art of acting and playing a character. I could never do any of my shows high or drunk … Underlying all of this is sexism and [misogyny] which proves that not only do we not get equal pay but we are still treated like heretics if we step out of line and think outside the box.”

What’s more, the icon continued to garner glowing reviews through her final show.

March 21, 2016: Judge MacDonald releases a written ruling in London that Madonna can withdraw her U.K. proceedings.

He did not rule on whether Rocco should be returned to New York to be with Madonna but did return the teen’s passport so he could visit his mother for Easter, if he so wished.

“As I observed during the course of the hearing, summer does not last forever. The boy very quickly becomes the man. It would be a very great tragedy for Rocco if any more of the precious and fast receding days of his childhood were to be taken up by this dispute,” the judge wrote. “Far better for each of his parents to spend that time enjoying, in turn, the company of the mature, articulate and reflective young man who is their son and who is a very great credit to them both.”

What’s Next: Whether or not his parents come to an agreement in the coming months, Rocco will likely remain in London at least until he finishes school.

In the meantime, his parents will continue working with their attorneys toward settling the custody dispute. If no agreement is reached, they are expected back in New York court for a hearing on June 1.