If this compound can undergo nucleophilic substitution, it can only be via SN1 fashion, as the reverse side attack in the anti-bonding $\ce{C-Br}$ orbital is blocked by the other bridgehead.
The reason that is often given why bridgehead carbon cations are not stable is strain. Strain itself is a concept that is difficult to grasp and it more often depends on what you choose as a reference system. For the sole qualitative purpose the cation is more strained than a non-constricted tertiary cation.
Another reason that is often given is that the carbocation cannot adopt a trigonal planar structure. While this is technically true, the deviation from an ideal trigonal surrounding is quite small; it's just about 25°. (DF-BP86/def2-SVP)
![molecular structure of norbonene cation](https://cdn.statically.io/img/i.sstatic.net/zEFWAm.jpg)
I believe the reason for this instability is a bit different. In $\ce{C+(CH3)3}$ the hydrogen carbon bonds can neatly align with the empty p orbital of the central carbon. Hence electron density can be transferred into this orbital or from another point of view, the positive charge can be delocalised into the neighbouring bonds.
![empty-occupied overlap in CMe3](https://cdn.statically.io/img/i.sstatic.net/yMQQ8m.jpg)
The above is just one example configuration calculated at DF-BP86/def2-SVP. It is not the lowest structure, but one chosen for the purpose of showing the overlap in the hyperconjugation. Since the molecule is not rigid at all and the methyl groups rotate, the stabilising effect will be there most of the time, in this conformation it is easiest to see.
That stabilising effect is not present for the carbon hydrogen bonds in proximity to the bridgehead. Those hydrogens actually point away from the cationic centre, hence overlap is not at all possible. Therefore the charge cannot be stabilised by those bonds.
![empty-occupied (non)-overlap in norbornane cation C-H to p](https://cdn.statically.io/img/i.sstatic.net/DR2LFm.jpg)
However, there is a small stabilising configuration between the carbon-carbon bonds and the unoccupied orbital and this is the reason, why bridgehead carbocations become more stabilized with larger ring structure.
![empty-occupied overlap in norbornane cation C-C to p](https://cdn.statically.io/img/i.sstatic.net/GPfkHm.jpg)
Like always there are a couple of different points at play, that help stabilise certain positions, or cease to do so.
So with the right motivation, a SN1 reaction might be possible.
Colourcode
Occupied orbitals are displayed in orange and blue, while virtual orbitals are displayed in red and yellow. Phases are chosen randomly.