The first thing for you, dear reader, to do is to take a look at the contemporary scholarship: "A Condemned Saint: Devadatta" (it's a PDF file; you might prefer the Google books version). You should also read Bhante Sujato's Why Devadatta Was No Saint to get a critique of Reginald Ray’s thesis of the ‘condemned saint’.
So now I'm assuming you've read "A Condemned Saint: Devadatta" - otherwise my "best guess" as to who Devadatta really was is going to seem rather weird!
Devadatta was a Sakyan like the Buddha; possibly they were cousins, more likely not particularly related. He possibly went forth in the first group of Sakyans after the Buddha's initial return to Kapalvastu, but it seems more likely to me that he was a good bit younger than the Buddha, so didn't go forth until some time much later.
He practiced well and clearly gained mastery of the concentration practices - and probably gained a good bit of insight as well. His learning was good enough that Sariputta even praised it upon at least one occasion.
He was a forest dweller - and found that lifestyle to be much to his liking and very supportive for practice. As the monastic community became more settled later in the Buddha's career, Devadatta felt the Sangha was going soft; that living in monasteries with fixed dwelling was Not so supportive of good practice. He felt that so much association with the laity was a distraction. In short he wanted a return to a more forest oriented, hard core way of life for the Sangha. So he proposed his 5 rules to the Buddha - which the Buddha rejected.
So Devadatta created a schism in the Sangha, drawing off some (the mythical 500) monks and set up a rival cult. This cult was quite successful, managing to survive at least into the 7th century CE. Because of this rivalry with a cult very close in doctrine, the mainstream Buddhist decide to paint Devadatta in a seriously bad light and wound up attributing to him all the nasty deeds we think of when we hear his name. (Think Catholics and Protestants in Northern Ireland.)
But the Buddha was indeed the wiser one - his system managed to not only survive, but thrive; whereas Devadatta's system was too strict and therefore never attracted the critical mass need for survival.
Clearly there is something seriously wrong with the traditional picture as preserved in the Theravadan vinaya. It says that after trying 3 times to kill the Buddha, Devadatta comes waltzing into camp (er, the monastery) and proposes his 5 new rules. Well, if Devadatta was known to be trying to kill the Buddha, he would never have been allowed close enough to the Buddha to propose the 5 rules! The story just doesn't make any sense. And the order of these events seems to be different in some of the other vinayas - perhaps, someone realized the weird order and cleaned things up.
Looking carefully at all the references to Devadatta in the suttas, all he is ever accused of is creating a schism - no mention of attempts to kill the Buddha or of Devadatta's own death. So I think Devadatta was a very serious practitioner who felt the Buddha and the Sangha were going soft, so he tried to return to a more austere way of practice.
It is possible that Devadatta was not even a contemporary of the Buddha! He might have come along later (tho not too much later given that his story is in the Mahasaghika vinaya and that split was about 100 years after the Buddha's death). But whenever he came along, he was very worrisome for the mainstream Buddhists.
On a personal note, I found the research in "A Condemned Saint: Devadatta" to be very interesting. It showed me how easily I could be persuaded to swallow a story - even one with the weird order of the Devadatta story. Many times I told the traditional story of Devadatta as part of one of my dhamma talks. It has been very helpful in reminding me to look carefully at ANY teaching. For years I have been telling my students to not take the stories in the suttas (let alone the vinaya) as literally true - that sutta study is about finding instructions on how to practice that are repeated in multiple places/circumstances - and then to go do those practices. It was kind of humbling to see I'd been taken in again.
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