Bankrupt Toni Braxton loses the copyright to 27 of her songs

A recently single and broke Toni Braxton has lost the copyright to 27 of her favorite songs.

The six-time Grammy Award winner has filed for bankruptcy not once but twice.

The 45-year old R& B singer was given the opportunity to purchase the copyright of some of her best hits from her music catalog for $20,000 when they were put up for sale on July 15.

But Toni was unsuccessful in her bid to buy back ownership of some of her most famous hits - including You're Making Me High and was outbid by another buyer TMZ reports.

Ross M. Klein doubled the low offer Braxton made and now he now owns the rights and can profit from hits like How Many Ways and Always.

Toni made a deal with the bankruptcy court to resolve her financial woes which included settling a whopping $150,000 debt last month. 

But despite her gloomy predicament she still owns the rights to her most famous hit Unbreak My Heart, which was not included in the auction - for now.

The loss of her music still comes as a bitter blow to Toni after a number of financial conflicts with her trustees.

Toni had previously filed for bankruptcy in 1998 for debts of $3.9 million and has legal trouble this year after her debtors tried to claim $754,000 in fees she made for International performances.

The singer and her trustee finally came to an agreement this week and agreed to pay the $50,000 she owed for the property and $100,000 from the performances.

She recently finalized her divorce from husband of 12 years, Keri Lewis. 

The split was amicable, Lewis is the father of her two sons, Denim, 11, and Diezel, 10 and they share custody of the children.

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