If you notice above, it is mentioned that if you enter in the last 30 minutes of a lottery, @lottobot will actually enter you in the next lottery, rather than the current one. @jaywon entered two posts consecutively as you can see in the bottom box in your image, but the entries were spaced a few minutes apart. The first was entered into lottery #17 (which was ongoing at the time), but the second one was actually entered into lottery #18 (the upcoming lottery at the time). This is because the second post was entered after the 30-minute threshold (it is actually a bit less than 30 minutes, but also somewhat variable)
If you notice above, it is mentioned that if you enter in the last 30 minutes of a lottery, @lottobot will actually enter you in the next lottery, rather than the current one. @jaywon entered two posts consecutively as you can see in the bottom box in your image, but the entries were spaced a few minutes apart. The first was entered into lottery #17 (which was ongoing at the time), but the second one was actually entered into lottery #18 (the upcoming lottery at the time). This is because the second post was entered after the 30-minute threshold (it is actually a bit less than 30 minutes, but also somewhat variable)
As for why @jaywon won both of these lotteries, I can only attribute it to beginner's luck :) The lottery winner is random: you can check out the logic here on @lottobot's repo on GitHub: https://github.com/ErikLetson/steem-lottobot . If you want to see the logic behind @lottobot's decisions, check this file specifically - https://github.com/ErikLetson/steem-lottobot/blob/master/lib/lottobot.py