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What did ex-Gladiators do after being freed? Did they stay near to what they knew or chose completely unrelated professions and prospered?

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In addition to harper89's answer, some gladiators were in the games to repay debts. Once they were repaid, they would return to whatever life they left before. With some luck, they would have earned a lot more than the debt, and thus be able to live off those earnings or invest them.

The most successful gladiators were also treated like modern day 'Pop Idols' with fan worship, fame and glory. It is therefore not surprising that some free men enrolled as gladiators. These free gladiators were ex-soldiers and some were wealthy Romans who craved the adulation and the glory given to gladiators. Other free men simply needed money to pay off their debts. Their living conditions were much better than the conscripted gladiators and they were given much more freedom and were allowed to leave the gladiator schools, or barracks.

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Some free men also would chose to enroll as a gladiator. @Sardathrion I hope you dont mind my small edit. +1 by the way. – harper89 Feb 29 '12 at 13:41
@harper89: Not at all! Thank you. – Sardathrion Feb 29 '12 at 13:57
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Once freed a Gladiator would become a Rudiarius and would be given a rudis which was a wooden sword that symbolized their freedom.

Some gladiators stayed near and with their rudis were able to take up training of other gladiators.

Others were even offered coin to return to the arena.

The Roman Emperor Tiberius (r. 14-37 AD) once offered 1,000 gold coins to retired gladiators (Rudiarius) who would agree to return to the arena.

Below is a list of the most common things a retired gladiator would do

  • To retire from the gladiatorial games altogether, living on the proceeds he had earned as a gladiator
  • To work as a bodyguard, and status symbol, of a wealthy Roman
  • To work in one of the gladiator schools training new gladiators
  • To work in the arena taking on a role of an arbiter, or referee
  • To continue working as an elite, sought after and well paid Rudiarius gladiator and continue to receive the adulation from the fans and spectators, opting for fame and glory or death

(Quote and bullet points also from this page)

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