Go to 1939 with 1 buck. Buy 10 Action #1’s. They go for a couple a million each. Even if you are worried about paper ageing, just buy a bunch of Walking Dead #1’s. Less than a decade old. In mint condition, $3.00 investment becomes thousands.
We know it’s possible for the time traveler to successfully win the lottery, as clearly it’s been done. There are people who won the lottery multiple times, defying odds of billions to one. At that point, time travel is a more likely explanation than happenstance (though rigging the lottery is an even likelier explanation, but the various lotteries say it ain’t so.)
The fact that this happened not just once, but that winning multiple times itself happened multiple times, makes these odds stupefying and time travel a solid hypothesis.
So, clearly, we have about two dozen time-traveling lottery players in our midst, and given the publicity photos, they either stay in our timeline between wins, or else, time their trips to make the intervals between winning match their biological aging.