In those days, Masters were allowed to have an entire group of Padawans, instead of being restricted to only one at a time. Jacoby was known to be quite rebellious, pushing the limits imposed by the Jedi Council. He also enjoyed teaching his students to think for themselves and to question all authority. His proudest moment, yet also most frustrating, was when his students began to question his own teachings. Jacoby felt that all rules and leaders needed to be challenged, if for no other reason to prove why they are necessary from time to time. Otherwise, it was time for a new rule or leader. His students immediately saw the logic and need for such attitudes.
It's well documented that attachment is forbidden for Jedi, but little is said of physical relations. Like most people, Jacoby's students felt it was implied that a life of abstinence was part of the rules for being a Jedi. Though he was a free-thinker and enjoyed challenging all rules put in place, Jacoby had often seen the need for no attachment in the Jedi Knights. And physical relations could certainly lead to such attachment. Even the most dedicated Jedi could still find themself obsessing over that night before, desperately tempted to call their lover back too soon and what not.
Jacoby taught his Padawans that when in desperate need of release, it was good to take matters into your own hands. Thus, the Jedi practice of Handing came about. Quickly, the Padawans would find themselves discussing how many times they "Handed" the night before, and began having competitions. This gave way to Group Handing sessions, so that they students could compare techniques. Word of what they were doing spread through out the Jedi Temple, and Padawans everywhere began to practice Handing. One Padawan, Chae Laciba, even threw a biscuit into the middle of the group. He declared that they must all Hand over the biscuit, and who ever was the final one to reach conclusion would have to consume the biscuit. It was fun and frivolity for all, but it was not without consequences.
And then one of the most cataclysmic events for the Galaxy spawning from the Jedi Temple happened: The Jedi Circle Jerk. Though seemingly harmless, and sounding completely benign, it would have incredibly impacting repercussions throughout the known Galaxy at the time.
As most of the Jedi Order was completely consumed with Handing, and almost exclusively in large groups now, the marshalling of the Galaxy and upkeep of peace and justice was falling to the wayside. Border dispute became all out wars because no Jedi ever showed up to help find a peaceful resolution. Criminal organizations and pirates were rampant. The most notorious space pirate of this era was of course Captain Jack Browneye and his crew of malcontents, who went completely unchallenged due to the Jedi Order's obsession with Handing. The Jedi became known as "Jerks", thus coining the name The Jedi Circle Jerk. The Galaxy slipped quickly into ruin, and the Jedi Council became all too aware that it was their fault. The Jedi Order had ended up forming intense attachment, only now it was to their own hands.
Obi-Wan Jacoby saw what had happened, and accepted full repsonsibility before the Council. He admitted that it was he who created Handing, and he had also pushed his students to go to town with it. He also declared that he would solve this horrible crisis.
Jacoby began to spread rumors through non-Jedi channels that Handing would actually lead to blindness. The Order of course caught word of this, but they blew it off. No pun intended. Handing continued, and Jacoby's Padwans even asked for their mentor to join in on sessions. Reluctantly, he agreed. But in truth, he did so only to make a needd sacrifice in order to help save the Galaxy. During a particularly tense session of biscuit, Jacoby "slipped", and issued directly into his own eyes. Screaming and writhing in agony, Jacoby revealed to the group that he had indeed gone blind from Handing. Word of this spread like wildfire.The entire Jedi Order ceased Handing altogether. It was never again spoken of, and always forbidden by any member. Instead, it was encouraged to fornicate with local floozies as long as attachment was never formed. It was known as the "love 'em & leave 'em" amendment in the Jedi doctrines.Jacoby's memory in the Jedi Temple is more of a grey one. The Order was, in time, able to bring justice and peace back to the Galaxy. Jacoby's ace pupil, Laciba, led the hunt for pirate Jack Browneye, ultimately ending his reign of terror within a year. Without handing, the Order once again had focus. Jacoby ultimately went down as someone who simply made a mistake, but his beliefs in challenging ideas was one the Order adopted. However, from that point forward no Master was ever allowed more than one Padawan at a time. It also wasn't long before the Council got really annoying and started micromanaging every Master, but that's a story for another time.
When the Jedi Council found a baby on Coruscant with an intense connection to the Force around the Old Republic year 24,990, it was foreseen that he would become one of the best Jedi Knights ever. They named him Obi-Wan Kenobi, part in honor of the Jedi Knight who made a large sacrifice for the Order as well as the Galaxy, but also in part to make the name Obi-Wan cleaner.