The recent flights to Jamaica have brought the government into conflict with the judiciary again. Whilst the media are unclear as to whether the injunction has actually been breached, it is a timely reminder of the power of the courts to ensure that the executive obeys its will.
Theresa May MP as the Home Secretary in 2012 became only the second Home Secretary to have been found in contempt of Court. The first Kenneth Baker, now Lord Baker, fell foul of the Courts in M v Home Office  UKHL 5, which established the Courts power to hold the office of SSHD in contempt. In that case the Courts had ordered the then SSHD to return an asylum seeker to the UK, the SSHD disobeyed. The SSHD was held in contempt.
In May MP cases, the SSHD had agreed to release an individual, within an interim order. The SSHD then purported to review that decision and not release the Claimant. HHJ Cotter QC sitting as a Deputy High Court Judge, disagreed that this was a lawful approach, and determined that the then Home Secretary was in contempt, and so joined that exclusive club.
May PM, then managed to achieve something no other PM has ever achieved before, when her Government was found in contempt of Parliament at the end of December 2018. Although contempt of Parliament is a very different concept to contempt of court, she did appear to be a trend setter.
The so what of a SSHD being found in contempt of court for a minister is little. The minister would not be personally held liable for a contempt caused by her department. However having been found in contempt the first time, if a Minister were then again to fail to comply with the Order or remedy the breach it seems likely that the minister would then be personally liable. I doubt the current government is willing to test the Courts and find out what happens on the second strike.