Stubborn pride or stupidity?

Okay, so I'm planning out a fic where the MC is an ex-con on "probation" which involves assisting Interpol/Police/Jennies with catching criminals. Part of the probation involves an assigned "Handler" who holds their Pokemon. The issue is that I wanna make it so the mons, or one in particular, pop out sometimes and see this random human who isn't their trainer, wearing the uniform of people who chased their little team in the past, holding their team's pokeballs, and proceeds to beat ass.

Realistically, the problem would be solved by letting MC hold onto their pokeballs, but due to probation requirements, the Handler must be the one holding them unless it's an emergency.

How would I write the Handler not doing the logical thing, without making them sound like a stubborn idiot/masochist.

TBC the Handler is supposed to be a good person, not a total idiot, but sticks to their job. I'm trying to make it so it isn't a pride-type thing.