Delaware Chancery Judge J. Travis Laster Thursday refused Anthem's (ANTM - Get Report) request to extend his previous order keeping the health insurer's reluctant merger partner in their $54 billion deal for another 60 days. On Monday Anthem asked Laster to continue a ban on Cigna (CI - Get Report) leaving the deal until July 7.
Cigna has asked the Delaware court to be freed from the deal and to rule that it is entitled to a $1.85 billion reverse breakup fee.
The vice chancellor did stay his order until noon on Monday, however, to allow Anthem time to decide whether to appeal to Delaware's Supreme Court. After Monday it would be up to the Supreme Court to stay Cigna's exit further.
Both a federal district court and an appeals have supported the Department of Justice's lawsuit seeking to stop the deal but last week Anthem asked the U.S. Supreme Court to review the case.
Rejection by Delaware's high court would essentially make Anthem's appeal to the U.S. Supreme Court moot.
Laster said during a hearing Monday that Anthem's bid to keep the deal together is a "long shot."
The companies have been bickering for months and Cigna announced plans to terminate the merger in February and filed suit in Delaware seeking to collect the breakup fee and $13 billion in damages from Anthem.
The two insurers' legal battle contrasts with the clean breakup carried out by two other health insurers, Aetna (AET) and Humana (HUM - Get Report) , which terminated their merger agreement in the wake of a federal judge's ruling in January blocking that $37 billion deal.
Aetna agreed to pay Humana a $1 billion reverse breakup fee as required by the companies' July 2015 merger agreement. After taxes Humana got to keep $630 million.