Suppose $X,X_1,X_2,X_3\dots$ is a $\mathbb{P}$-i.i.d. family of $[-1,1]$-valued random variables with $\mathbb{E}[X] = 0$.
Hoeffding's inequality implies that \begin{equation*} \forall T \in \mathbb{N}, \forall \varepsilon > 0, \qquad \mathbb{P}\bigg[\frac{1}{T} \sum_{s=1}^T X_s \ge \varepsilon\bigg] \le \exp\Big(-\frac{T}{2}\varepsilon^2\Big), \end{equation*} from which it follows that \begin{equation*} \forall T \in \mathbb{N}, \forall \delta \in (0,1), \qquad \mathbb{P}\bigg[\frac{1}{T} \sum_{s=1}^T X_s \ge \sqrt{\frac{2}{T}\log\Big(\frac{1}{\delta}\Big)}\bigg] \le \delta. \end{equation*}
Basically, this result states that the trajectory of the process $Y_t := \frac{1}{t}\sum_{s=1}^t X_s$ is below the threshold $\sqrt{\frac{2}{T}\log\Big(\frac{1}{\delta}\Big)}$ with probability at least $1-\delta$, at any prescribed time $T$.
Instead, suppose that we wanted the whole trajectory $Y_1, Y_2,\dots,Y_T$ under the thresholds $\sqrt{\frac{2}{1}\log\Big(\frac{1}{\delta}\Big)}, \sqrt{\frac{2}{2}\log\Big(\frac{1}{\delta}\Big)}, \dots, \sqrt{\frac{2}{T}\log\Big(\frac{1}{\delta}\Big)}$, where $T \in \mathbb{N}$ is fixed. Can we do any better than using the following union bound
\begin{equation*} \mathbb{P}\bigg[\bigcup_{t\in\{1,\dots,T\}} \bigg\{\frac{1}{t} \sum_{s=1}^t X_s \ge \sqrt{\frac{2}{t}\log\Big(\frac{1}{\delta}\Big)}\bigg\}\bigg] \le \sum_{t=1}^T \mathbb{P}\bigg[\frac{1}{t} \sum_{s=1}^t X_s \ge \sqrt{\frac{2}{t}\log\Big(\frac{1}{\delta}\Big)}\bigg] \le \delta\cdot T ? \end{equation*}
The problem with this last inequality is that a multiplicative factor $T$ appears in the bound, and I feel that maybe, due to something in the spirit of maximal martingale inequalities, we can do much better.
Any suggestion or pointer to the literature is very welcome.
EDIT: I tried to perform some simulations. Taking $X_1,X_2,\dots$ as a $\mathbb{P}$-i.i.d. family of Rademacher random variables seems to suggest that at least something of the form \begin{equation*} \forall T \in \mathbb{N}, \forall \delta \in \Big(0,\frac{1}{10}\Big), \qquad \mathbb{P}\bigg[\bigcup_{t\in\{1,\dots,T\}} \bigg\{\frac{1}{t} \sum_{s=1}^t X_s \ge \sqrt{\frac{2}{t}\log\Big(\frac{1}{\delta}\Big)}\bigg\}\bigg] \le \delta\cdot \log(T) \end{equation*} holds, and even something better than this (maybe, even an upper bound of the form $O(\delta \cdot \log\log T)$).