John Connolly Week: (7 of 10) – The John Callahan Story

The injustice is great in one sense because when Connolly was first prosecuted he was charged with obstructing justice by leaking information about John Callahan. The jury found that not proved.

Here are the facts: . Callahan was a wannabe gangster. A bright guy, a CPA, he had a good legitimate job during the day but notorious friends at night. He got fired from one job as president of World Jai Alai (WJA) because some good work by Connecticut detectives showed he hung around with the low lives including John Martorano’s brother Jimmy, a Mafia guy.

Callahan recognized that WJA was a cash money pit. He wanted to get back into that business. He tried to buy WJA from Roger Wheeler a legit guy and smart businessman out of Oklahoma. They could not agree on terms.

Callahan went to Miami, where WJA is headquartered to meet with John Martorano then a fugitive from justice. Martorano was known as a cold stone sneak murderer of at least 20 people. He bragged how he murdered unarmed people who he felt might be government witnesses against his friends. Imagine what he would do if he knew one was to be a witness against him.

Callahan paid Martorano $50,000 to murder Wheeler. He promised him a $10,000 weekly cut of the business once he took over. Martorano flew to Oklahoma and shot Wheeler in the head as he got into his car at a country club. Callahan’s hope that Wheeler’s widow would sell the business to him was dashed when she refused.

There was going to be no weekly cut for Martorano. Martorano is obviously not happy. Beyond that, Martorano knew that there was only one person who could implicate him in Wheeler’s murder, that was John Callahan. Well that’s not quite correct, the guy who helped him Joe McDonald might have done it but Joe was no risk for he too was a stone cold killer.

Wannabees like Callahan don’t have the gangster instinct. He should have known his life would not be worth a plug nickel if Martorano sensed he might give him up.

The unexpected happened. Good detective work by a Tulsa police detective had him trying to connect Wheeler’s murder to Callahan. The FBI in Tulsa tried to help. It sent requests to Boston FBI for information on Callahan and his associates. Connolly’s boss, John Morris, made sure Connolly got the requests. He buried them. After all, that was his job to protect them.

Finally pressure came from Tulsa, Connecticut and Florida that could not be ignored.  Both Whitey and Flemmi were asked to take photographs which were to be sent to Tulsa. Connolly was asked to interview Callahan. The word got back to Martorano that the one guy in the world who could jam him in on a murder was being looked at by the FBI.

The expected happened. Martorano (and Joe McDonald) put a bullet into Callahan’s head when he arrived at the Fort Lauderdale Airport for a meeting. Martorano could now breathe easy.

How does Connolly fit into this? Martorano, who never met Connolly made a deal with the federal prosecutor to testify against Connolly. He did so because he thought if Flemmi made a deal before him, “It’s not beyond the realm of possibility that if he starts talking about the murders, he could walk our of [prison] , no murder raps, no forfeitures, no nothing” and “we’re locked up forever.” 

Martorano would do only 12 years in prison. As a bonus for his cooperation he got $20,000 on his release for prison, $1,000 for each victim he murdered. In exchange Martorano agreed to put the blame for Callahan’s murder on Connolly. He would say that Connolly told Whitey and Flemmi to tell him that the FBI was going to pressure Callahan and if Callahan talked they’d all end up in jail.

Of course it was a fairly tale but if you are facing the death penalty as Martorano was if Flemmi beat him to the trough it wasn’t too hard to spin one. That Callahan was being targeted by the FBI was common knowledge.

Corrupt Agent Morris led the FBI  task force protecting Brian Halloran who was wearing a wire. He was trying to entrap Callahan. Word around town was both Halloran (out on bail on a first degree murder charge) and Callahan were hot. Martorano didn’t need anyone to tell him what he had to do.

Even assuming Connolly did tell them Callahan may cooperate then wasn’t that part of his promise to protect them. Didn’t the FBI authorize him to do this? Morris testified Connolly told him his deal with them was to give them a head’s up, that is tell them what’s going on and warn them if paper was out on them. He had no problem with that as Connolly’s supervisor.


8 thoughts on “John Connolly Week: (7 of 10) – The John Callahan Story

  1. Matt
    It too bad dead men cant talk because I still to this day dont see how Callahan thought he could get Wheeler’s widow to sell the business. How could John Callahan think that someone as wealthy as Roger Wheeler could be murdered in cold blood and not have it thoroughly investigated? Were there not other motives for Callahan to have Wheeler murdered? Also how come Callahan let his guard down by agreeing to meet with Martorano at Ft Lauderdale. Actually anywhere after knowing FBI were looking into him. Something seems off about the whole Roger Wheeler murder to me in that its just a crazy plan to try and gain control of the World Jai Alai company no?

    1. Jerome:

      1. He and Wheeler were involved in discussions relating to its sale. Wheeler was interested in getting out of the business. I figured Callahan thought that after Roger Wheeler was dead his wife wold have little interest in running a business in Miami involved in gambling so would be happy to dump it.

      2. I’m not sure he thought much about the follow up investigation. Perhaps if he did he thought it unlikely it would come back at him. He’d have his alibi. Keep in mind no one was ever tied into the murder until Martorano made a deal and confessed around 15 years later.

      3. I don’t think Callahan had other motives. He saw a cash cow. He had been removed from having a part in it, he wanted back in which he could have if he bought it.

      4. Better question is how could Callahan think he could have a stone cold killer like Martorano kill someone for him and it not come back to bite him. My answer to that could only be he felt that once he was able to buy business he could keep Martorano happy with money. But as a smart guy he should have figured that he was the only witness who could link Maetorano to the killing of Wheeler so his life wasn’t worth a plug nickel. He let his guard down because he never figured that stuff out. He probably thought he could convince Martorano he was a stand up guy so he had nothing to fear from him. He didn’t figure Martorano would risk his freedom hoping Callahan would stand up.

      5. Of course it seems off but greed often blinds men to the perils involved in their undertaking.

  2. Matt: I think Connolly should tell his side of this story in his own words. And it would be great if a couple of the former FBI agents who support Connolly would publicly back his version of events.

  3. Callahan was fired because Paul Rico, then retired from the FBI and responsible for Security at the World Jai Alai Company, learned that he was hanging around with Whitey and Martorano in Boston. Callahan was president of the World Jai Alai Company and his having criminal associates like those guys jeopardized the company’s license. It was Paul Rico who brought that information to the attention of the World Jai Alai Board that promptly met and fired Callahan. Rico did exactly the right thing.


    1. Joe:

      I read your book RICO and recommend everyone read it. I don’t know if you mentioned it in your book but I have a simple way of knowing that Rico was not corrupt. If he were Raymond Patriarca nor any of the other Mafia leaders wouldhave gone to jail as a result odf his work. Salemme, Martorano, and Flemmi, but especially Salemme who tells stories about Rico’s corrupt acts which allegedly were going on at the time of the Mafia prosecutions would have been able to set him up so that he never would have been able to go through with the prosecutions.

      The absurd story about Rico needed a toss away gun so that he could murder one of the McLaughlns but didn’t do it because only 4 (or 3) of the FBI agents would go along with it but one wouldn’t. As a former agent I’m sure you experienced other agents asking you if you would go along with murdering people. Obviously it never happened but it was believed by the federal prosecutor. Even the tip off to Salemme and Flemmi to flee after the indictments for the bombing of lawyer Fitzgerald’s car each one told a totally different story.

      Then most preposterously Martorano says Rico is in on the hit of Wheeler. Martorano who is then on the lam does the hit. Now if Rico was in on it the last thing he would do is to meet in his office with Martorano and Flemmi. He would have stayed a million miles away from him or if he was going to meet it would have been in an out of the way place.

      Then the purpose of the meeting is absurd. Martorano says Joe McDonald who helped him murder Wheeler and Callahan wanted to know if the deal to buy World Jai Ala> was dead. Wouldn’t they have known that without asking Rico? They murdered the guy who was going to buy it. Only a blind and dumb prosecutor would believe a guy saying he wanted to know if the deal to buy something was dead when he knew the guy saying it killed the buyer.

      Rico was framed. No doubt in my mind.

      1. Matt
        You are correct. It would be impossible if Paul Rico was corrupt for the big guy, Raymond Patriarca, to go to jail without raising the slightest comment about it. Salemme, who is obviously not the brightest bulb in the box, told stories that are on their face absurd and silly. It is hard to believe anyone, much less an experienced prosecutor would believe them.

  4. Amazing story, Matt. Ought to make a movie out of it.

    That said, I read Black Mass many years ago. How much of that book is fiction?

  5. Hi Matt and thanks for an interesting article.

    Do you think that the deal that the FBI handlers had with their top echelon informants is to tip them off about indictments and to protect them from police investigations and in exchange the informants will give them information about the Mafia figures that they know?

    Why did Flemmi refuse to become inducted into the Mafia as didn’t Baione offer him a chance to become a made guy?

    Were Halloran and Callahan close friends?

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