In general usage, if you say someone is currently (now, in the present) “attempting to do something”, it means he has not actually successfully done it yet. Hence he is “attempting” to do something. Eventually he may succeed, but that time has not come yet.

If you are talking about an event that has already passed, like Iketani’s jump over the “monster box”, then “attempt” takes on the meaning of “failure”. “Here’s a video of Iketani attempting to jump over the box” would normally be interpreted as “Here’s a video of Iketani failing to clear the box”, since if he succeeded then his attempt was successful, hence he is no longer “attempting” to clear the box.

Something like “Here is a video of Naoki Iketani facing the challenge of jumping over a 21-level ‘monster box’” would avoid giving away the result (which is what James was aiming for), and as it is neutral in tone it would remove the reader’s preconception that the attempt was going to end in failure.

I think the title is fine… I was pleasantly surprised when he made it over the box.