Team Jiraiya
*The Team Jiraiya image was looted from wikipedia.org
Here’s another possiblity that Pein and Konan were Jiraiya’s students before together with Yondaime. The girl closely looks like Konan. Her hairstyle is definitely identical with Konan’s. However, the other guy doesn’t look similar to Pein. He looks like Choji a lot. 
But I have a gut feel that they are Konan and Pein in the picture. I calculate Jiraiya’s familiarity with Konan and it results to “Konan is a former student of Jiraiya”. I also strongly feel that Pein and Konan is of Yondaime’s generation. The fact that Konan calls Pein by his name, proves that they have been close enough and the only possiblity I can think of right now is that they were best friends. And best friends usually belong to same team.
Disclaimer: This is just my opinion. You can reject or accept it, you are free to comment.
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September 28th, 2007 at 2:53 am
The reason why the other guy in the picture doesn’t look like Pein is because Pein shapeshifts. haha
October 1st, 2007 at 11:54 pm
[...] like another speculation of mine has been proven wrong. I guessed on my previous post that Konan and Pein were Yondaime’s teammates. I believe I had an educated guess though. But [...]
October 4th, 2007 at 1:01 am
i really believe that konan and pein were not on yodame’s team but were seprat students of Jeraiya. i think this cuz if you read the newer chapert closely there is a threed nin that was with konan and pein when they came to jeraiya….Nagato…remamber?
February 10th, 2008 at 4:47 am
noob read the manga, they were his old students that orochimaru wanted to kill but he didnt let them and he stayed with them for like 1 year or 3 i forgot, but he stayed with them and trianed them so they oculd fite for themselves and live bitch! but that kid that b ecame pain(black haired boy) became evil and banged konan up the butt~
June 14th, 2008 at 8:56 am
i think you r right or wrong i dont know
June 14th, 2008 at 8:58 am
i think your right or wrong i dont know
October 10th, 2008 at 6:40 am
yes there were a spreate team there was a war going on in the five contries and the hidden waterfall village was in between it and there family was killed and then jiaiya took them in for three years and tout them some jestu’s and pein was said to be the succer of the person who found and started the ninja world and was said to be a god that was desided to have the eyes of pein. And konan and pein became the leaders of the akataski . but the third person who he tought with them has not been said were he is. And Jiraiya did leave them to fend for them self and went back home to kohana.