“I Retire”: Career Prisoner Announced Retirement At 66th Conviction

Ricky Q. Caldwell, 52, has announced his retirement.  Caldwell’s career was crime and, like Michael Phelps and Michael Jordan, he has previously announced his retirement. However, when called before the court for his 66th conviction, Caldwell told Court Justice Richard C. Kloch Sr.  “In my illustrious career, I apologize, and I retire.” 


Of course, with 66 conviction, it is hardly an “illustrious career” and more of an infamous career.  His latest crime was the robbery of  a man in his car outside a 7-Eleven store in Niagara Falls.  He is now going back to prison for the sixth time in this life.

The retirement announcement however was the same in 2013 when he was before Niagara County Judge Sara Sheldon and accused of shoplifting and pulling a knife on a clerk at the Family Dollar store.   In the latest crime, he was undone by leaving his glasses in the victim’s car.

Despite his long record, Caldwell was allowed a plea bargain to a reduced charge of attempted second-degree robbery with the minimum sentence of three years behind bars and five years of post-release supervision.


27 thoughts on ““I Retire”: Career Prisoner Announced Retirement At 66th Conviction”

  1. Celebrity time.

    Tennis star Venus Williams T-boned a car in Florida, killing a 78 year old man.

    The tennis great blamed the crash on heavy traffic that left her vehicle jutting out into the intersection, according to the report. Cops did not believe she’d been distracted by a device or under drug or alcohol influence.

    I’ve been driving all kinds of vehicles for 40 years & never got into a t-bone crash Venus!

  2. He bragged that his career in crime was “illustrious”, and he was able to plea down his sentence? 66 convictions and only 6 times in prison? Does that mean that each stint was 11 counts, or has he been able to successfully negotiate his way out of serving time?

    Because I would say that at his 66th conviction, the public needs a break. He should not be allowed to plea bargain a day off his sentence. He’s a slow learner, and not a very good criminal if he keeps getting caught. And at 66 convictions, I can’t see how he would be employable. It would be a liability to any employer to hire him. The employer would be putting customers and other employees in jeopardy.

    Sometimes, people are just a menace to society. And they are so far gone, that going straight and narrow doesn’t seem like either a likelihood, nor a real possibility, because the intent of his record renders him unemployable. Some people just need to be locked up because they refuse to stop preying on the rest of us. If you won’t live with us peaceably, then go behind bars where you can’t do any more carnage.

  3. “i”ve been working on the chain gang!
    Alll the live long day!
    New York is my home state!
    It is just a smile away.
    Don’t you hear the whistle blowing?
    It is early in the morn.
    You can see my work this eveninge.
    We will be a mile away.”

  4. John Gotti Jr. wants to retire from the Gambino crime family. Here’s the interview.

  5. This is tabloid material, no details, no thought gone into it.

  6. He expects to get out early to run for Congressin Charley Rangel’s district when Charley retires.

  7. Predators can’t be tamed & don’t retire. When will judges figure it out?

    1. TJ – there are some statistical studies showing some violent criminals start to age out. And certain categories age out early.

  8. whatever!! when, if ever is JT gonna bring up the DNC fraud lawsuit???

  9. The prosecutor agreed to a 3 year sentence for pulling a knife on a sales clerk at a downscale store. I wonder if he would have gotten the same deal if he pulled a knife on an assistant prosecutor?

  10. 66 convictions and this ONLY his 6th prison stint? Those numbers don’t add up.

    Something is rotten in Denmark, er ah, New York!

    1. I was puzzled by that as well.

      66 convictions and only 6 times in jail suggest he is truly a master at something.

      Perhaps he should have tried politics or religion.

      The pay may not be much better, but at least the paydays are more regular.

  11. The state needs to provide this man with a duly fitting retirement. It’s called incapacitation.

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