Jon Skeet is about 143K reputation above the next highest users. Furthermore, he has over 27,000 posts. He hit the reputation cap today 6 hours in to the day. Most likely, he will get 200 reputation even if he doesn't answer another question for a long time to come. But that will limit his ability to get accepted answers, dropping his rate down some. This quarter, he has earned 27.6K reputation. We are almost through the quarter, let's say there's been about 85 days, or 17K reputation via the cap. That means he earned 10K extra reputation through either bounties or accepted answers over the reputation limit. Okay, so what does all of that mean?
If Jon Skeet passively quit today, he would likely still continue to get 200 reputation most days for some time to come. A better estimate can be found by what his "Passive" reputation is, which can be easily found via "My Money for Jam". This would be great, but it unfortunately crashes for Jon Skeet. So I looked around a bit more and found an interesting query, "Staying Power". And that one crashed too... As MikeD mentioned in the comments, with some approximations, his passive reputation is averaging 900, and his older than 4 years is averaging 292, so he's probably going to repcap most days for some time to come.
In the same time, if one of his closest competitors kept up, he would lose his lead by about 13K/quarter (Highest reputation this quarter is 30K as of writing). So that means he would stop being the highest reputation user in about 11 quarters, give or take, or 3 years. But most likely he would not continue to get 200 reputation every day if he passively quit for 4 years. If he stopped increasing his reputation entirely, he would likely have the lead for about 1 year, assuming people kept up their rate. Thus, I would state that it would probably take at least 3 years before anyone overtook him, if he passively quit today. And it would take even longer if no one was actually trying to manage the task, and people suddenly stopped upvoting his answers, which seems unlikely.
Fudging the numbers even more, and given the likelihood that no one would keep up that extreme rate for the time required to make it happen, I'd say his lead is probably safe for at least 4 years, maybe longer, if he stops answering questions today. But that just wouldn't be any fun...
Even if he keeps his current rate, he is 2K below the top person for the quarter. At that rate, given the #2 user, he could keep his #1 spot up for about 20 years, with his recent "Slacking" rate of only ~28K/quarter.