The couple's divorce battle has become bitter, and late last year a request from the actor to see more of their six children was rejected.
Now, a source told the Mail on Sunday that he has told friends it has been the "worst holiday season" of his life as he tries to come to terms with the breakup.
"He desperately misses having his kids with him for Christmas and New Year," the insider added.
"He's broken down in tears so many times - he's not ashamed to cry anymore. Brad is like a broken man."
It comes weeks after Pitt's lawyers stated that Jolie "has no self-regulating mechanism" to prevent sensitive information about their children and divorce becoming public through the media.
The actor's legal team filed a memorandum in a Los Angeles court on December 21 explaining to a judge why he wants information about the divorce and the custody of their six children sealed from the public.
In the paperwork Pitt, 53, accuses Jolie, 41, of compromising their children's privacy and not acting in their "best interest".
The move from Pitt comes weeks after a judge refused to take emergency action to seal the file but told the actor he could apply for the case to be sealed in January 2017.
Pitt's lawyers also drafted a proposed order which they would like the judge to approve at the January hearing, which will be at a court in Los Angeles.
Earlier this week Brad's demands to see more of his children were rejected by his ex-wife as their divorce battle became increasingly bitter, and the star was said to be facing a Christmas alone.
The details emerged as the actor's request to seal sensitive court documents in his custody fight with the Tomb Raider star was denied by a judge.
However, Superior Los Angeles Court Judge Richard Burdge Jr did not rule out sealing specific documents, including those related to the couple’s children.
Before the hearing, which neither Pitt and Jolie attended on Wednesday, lawyers for both sides reportedly submitted information via emails to the court that shed light on the increasingly acrimonious dispute involving access to their six children.
The actor’s attorney Lance Spiegel claimed in one that while his client has complied with the child therapy process, 'the therapy team has ignored or disregarded issues that [Brad] has raised.'
He added: 'Regardless of [the therapists’] views, there is no reason for Brad not to request court orders for more access to the children.'
At the end of November Pitt’s lawyers had asked Jolie’s legal team if the actress would agree to greater visitation during December between him and the children, in a number of 30 to 60 minute monitored sessions.
US website TMZ states the mum-of-six rejected the request.
Her attorney Laura Wasser accused Pitt and his attorneys of ignoring the best interests of the children as decided by the therapists.
Currently a temporary custody arrangement is in place that sees Jolie have custody of the children as professionals make decisions about visitation.
Comments