Kennedy, Sinatra and the Mob Connection

Karen Isaacs

Long Wharf Theater is presenting, depending on how you look at it, either an inventive way of viewing JFK's election and assassination OR glib pandering to all political conspiracy theorists. You will have to decide for yourself which is more accurate.


Ride the Tiger by William Mastrosimone offers some witty lines and intriguing situations but he seldom takes full advantage of either. Whether that is the fault of the play, the direction or the cast is up for debate.


Ride the Tiger purports to reveal the relationship that Frank Sinatra and mobster Sam Giancana played in the election of JFK to the presidency and beyond. Certain facts are not in dispute: Kennedy was a serial womanizer; and one of the many women he was involved with, even after he entered the White House, was Judith Exner. Judith Exner also was a mistress of Sam Giacana, the mobster who "owned Chicago." Giancana was involved in a plot to kill Castro.


Mastrosimone, who wrote the script for the mini-series Sinatra, has said that after extensive interviews with Sinatra, he decided to create "plausible scenarios" for the interactions between five prominent figures: Joe Kennedy, JFK, Sinatra, Giancana and Exner. How plausible you think these scenarios are is in dispute.


Some things are accurate: JFK felt he needed to counteract the anti-Catholic sentiment in early primary states such as West Virginia; union support was essential; Joe Kennedy was actively involved in the campaign; JFK knew Sinatra, partly through brother-in-law, actor Peter Lawford. JFK had an on-going affair with Exner.


The problem for the play is that Mastrosimone jumps from these facts to some conclusions that will lead at least some of the audience scratching their heads. What emerges is a blending of Oliver Stone's conspiracy theories about the assassination of JFK AND the salacious, dubious celebrity biographies of Kitty Kelly. The play ends with Giancana hinting that he will "get" both JFK and RFK for various slights; is this a hint that he played a role in both assassinations? That is certainly the implication with which Mastrosimone leaves us.


The cast is given the difficult job of presenting larger-than-life figures with whom most of us are very familiar -- certainly that is the case for Douglas Sills as JFK and Paul Anthony Stewart as Sinatra. These two performers have the most difficulty. Sinatra, as portrayed by Stewart, is less the cocky, polished performer and more, as I overheard one audience member say, "like a deer in the headlights." Sill's JFK is more juvenile frat boy than war hero, Senator and presidential candidate.


Because the other characters are less well known to us, the actors come off better, particularly John Cunningham as Joe Kennedy and Jordon Lage as Sam. Lage captures the swagger of the mobster, but he also has the most fully written part.


Christina Bennett Lind is given the unenviable task of playing Judith Campbell Exner. Unfortunately, the author has not decided whether she is somewhat intellectual and artistic, a professional bimbo, or just dumb and naive. Her actions make little sense.

Gordon Edelstein has directed this mishmash as well as can be expected given some of the problems with the script.


But if you expect the wit of Gore Vidal, as in The Best Man, Ride the Tiger will seem like a weak imitation.


Ride the Tiger is at New Haven's Long Wharf Theater through April 21. For tickets and information call the box office at 203-787-4282 or online at


This review appears in Shore Publishing Community Newspapers April 17, 2013 and online at

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