Let $B_t$ be a Brownian motion, and let $S_t = \sup_{0\leq s\leq t}B_s$. Show that $T := \inf \{ t \geq 0 : B_t = S_1 \}$ is not a stopping time.
It suffices to show e.g. $\{T \leq 1/2\} \not\in \mathscr{F}_{1/2}$ . This amounts to proving, $$\left\{ \sup_{s\in [0, 1/2]} B_s \geq \sup_{s\in [1/2, 1]} B_s \right\} \not\in \mathscr{F}_{1/2}$$
This seems pretty obvious to me: at time $t = 1/2$, you know $\sup_{s\in [0, 1/2]} B_s$ is some number, but cannot tell whether or not $B_s$ will cross above that number in $s\in [1/2, 1]$. But I am stuck figuring out how to make this intuition rigorous.