Markovnikov Rule of Alkenes
My suggestion is to stop trying to predict the product by rules like “rich becomes richer” or “proton goes to carbon having greater number of hydrogens attached to it”, etc. for Markovnikov addition and opposite for anti-Markovnikov addition.
These are subject to many exceptions.
Instead, draw the direction of dipole in the molecule at the site of the double bond, (order of precedence: +R effect, +H effect, +I effect for considering direction). After doing this, $\ce{H+}$ will attach the carbon with δ− charge (as electrophile will attack first, and carbocation formed on δ+ carbon which is more stable), and nucleophile going to other carbon atom in case of Markovnikov addition.
The opposite holds for anti-Markovnikov addition, i.e. $\ce{H+}$ will attack carbon with δ+ charge.
Now coming to your question. After you figure out on which carbon $\ce{H+}$ will attack, the carbocation can further be stabilized by Hydride shift (always check for rearrangement possibilities like hydride, methyl, ethyl shift, ring expansion, etc.). After rearrangement only does the nucleophile $(\ce{Br-}$ here) attack.