Show me a Prime Minister that has not pushed the boundaries at some stage?
Sometimes it is the only way to make progress rather than sitting twiddling your thumbs, much like the current situation!
Defining "getting caught" is also subjective.
Remember all those High Court/Court of Session judges that initially called the prorogation of Parliament "political" rather than unlawful?
It was the Advocate General for Scotland that carried on the legal challenge until the "right" verdict was delivered.
Now who was right & when is a moot point - you will take one side and I would take the other - but the job in hand was done.
Politics is in a mess because those in charge have little connection with the people they serve and, invariably, look after themselves first and last.