Jake Esterline

Jake Esterline

Jacob "Jake'' Esterline was born in Lewistown, Pennsylvania, on April 26, 1920. When he was eighteen he enrolled as an accounting student at Temple University in Philadelphia. In 1941 he joined the Officer Candidate School at Fort Benning.

During the Second World War Esterline was recruited into the Office of Strategic Services (OSS). Esterline was sent to India in early 1943. Later that year he was infiltrated into Burma. By the end of the war he had became a commander of a guerrilla battalion fighting the Japanese Army in China.

Other important figures working in China during this period include John K. Singlaub, Ray S. Cline, Richard Helms, E. Howard Hunt, Mitchell WerBell, Jake Esterline, Paul Helliwell, Robert Emmett Johnson, Jack Anderson and Lucien Conein. Others working in China at that time included Tommy Corcoran, Whiting Willauer and William Pawley.

After the war Esterline finished his accounting degree. He then worked for a family law firm in Pennsylvania. On the outbreak of the Korean War Esterline joined the Central Intelligence Agency (CIA). He was sent to work at what became known as "The Farm" - a clandestine training school for CIA recruits at Williamsburg, Virginia. Esterline was put in charge of guerrilla warfare training.

Jake Esterline in China during the Second World War.
Jake Esterline in China during the Second World War.

Esterline went to work for Frank Wisner, head of the Directorate of Plans (DPP) an organization that concentrated on "propaganda, economic warfare; preventive direct action, including sabotage, anti-sabotage, demolition and evacuation measures; subversion against hostile states, including assistance to underground resistance groups, and support of indigenous anti-Communist elements in threatened countries of the free world."

In 1954 Esterline was placed in charge of the CIA's Washington task force in the successful overthrow of Guatemalan President Jacobo Arbenz. Esterline also served as CIA station chief in Guatemala, Venezuela and Panama.

Richard Bissell, the new head of the Directorate of Plans, appointed Esterline as Task Force Chief for the Bay of Pigs invasion. He was also involved in the plot to assassinate Fidel Castro. In an interview he gave to Don Bohning of the The Miami Herald just before his death, Esterline admitted that Juan Orta, who functioned as Castro's private secretary, had been recruited to slip a poisoned pill into a drink. However, a few days before the invasion Orta changed his mind and fled to the Venezuelan Embassy.

When Esterline discovered that the assassination plot against Castro had failed he had serious doubts about whether the Bay of Pigs operation would be a success. Esterline and Jack Hawkins, Chief of Paramilitary Staff, were also unhappy about the decision to change the landing site from Trinidad to the Bay of Pigs. On 8th April, Esterline and Hawkins went to see Richard Bissell and told him they wanted to resign. Bissell persuaded them to stay and be "good soldiers".

In February, 2005, Gerry P. Hemming claimed that it was Esterline and not David Atlee Phillips who was Maurice Bishop, the man who met with Antonio Veciana and Lee Harvey Oswald in August, 1963, in the building that housed the office of Haroldson L. Hunt in Dallas.

Esterline also served as chief of the CIA's Miami office (1968-1972) and as deputy chief of the agency's Western Hemisphere division. Esterline retired from the CIA in 1978.

Jacob "Jake'' Esterline died at Hendersonville, North Carolina, in October, 1999.

Primary Sources

(1) J. S. Earman, Memorandum (25th April, 1967)

We find evidence of at least three, and perhaps four, schemes that were under consideration well before the Bay of Pigs, but we can fix the time frame only speculatively. Those who have some knowledge of the episodes guessed at dates ranging from 1959 through 1961. The March-to-August span we have fixed may be too narrow, but it best fits the limited evidence we have.

a. None of those we interviewed who was first assigned to the Cuba task force after the Bay of Pigs knows of any of these schemes.

b. J.D. (Jake) Esterline, who was head of the Cuba task force in pre-Bay of Pigs days, is probably the most reliable witness on general timing. He may not have been privy to the precise details of any of the plans, but he seems at least to have known of all of them. He is no longer able to keep the details of one plan separate from those of another, but each of the facts he recalls fits somewhere into one of the schemes. Hence, we conclude that all of these schemes were under consideration while Esterline had direct responsibility for Cuba operations.

c. Esterline himself furnishes the best clue as to the possible time span. He thinks it unlikely that any planning of this sort would have progressed to the point of consideration of means until after U.S. policy concerning Cuba was decided upon about March 1960. By about the end of the third quarter of 1960, the total energies of the task force were concentrated on the main-thrust effort, and there would have been no interest in nor time for pursuing such wills-o'-the-wisp as these.

We are unable to establish even a tentative sequence among the schemes; they may, in fact, have been under consideration simultaneously. We find no evidence that any of these schemes was approved at any level higher than division, if that. We think it most likely that no higher-level approvals were sought, because none of the schemes progressed to the point where approval to launch would have been needed.

(2) Evan Thomas, The Very Best Men: The Early Days of the CIA (1995)

It never occurred to Bissell that if push came to shove, Kennedy wouldn't put in his stack," said MacBundy. "He never said, "Do you really mean it? If we get the beachhead, will you back us up?" These worries were covered up. Once engaged, Bissell believed, Kennedy wouldn't allow it to fail." Bundy or Kennedy himself should have pressed Bissell to own up to his real expectations and intentions. It is the job, particularly, of the national security adviser to prevent misunderstandings between the president and his foreign policy advisers. But Bundy was a little too trusting and admiring of Bissell, as was the president. And Bissell was too sure of himself and his plan to fully seek their advice as well as consent. The cheerful, damn-the-bureaucrats bond between the CIA and the New Frontiersmen was a curse.

Back at Quarters Eye, Colonel Hawkins and Jake Esterline, the project director, worked through the night to produce a plan for the White House that was less "noisy." A few days later Dave Phillips, the propaganda chief, walked into the war room and noticed that someone had scrawled a large red "X" over the town of Trinidad. "There's been a change in the plan," said Colonel Hawkins. "Trinidad is out. Now we are going to land here." He pointed to an area on the coast a hundred miles to the west. Phillips laughed when he saw the name. "Bahia de Cochinos? How can we have a victorious landing force wading ashore at a place with that name? How can propagandists persuade Cubans to join the Brigade at the Bay of Pigs?"

Phillips squinted at the map. "It's too far from the mountains," he said. The invaders were supposed to be able to "melt into the mountains." Now the Escambray Mountains were eighty miles, away-across an impenetrable swamp. "How will the Brigade take' the beach and hold it?" he asked Hawkins.

"The first ships to land will carry tanks."

"Tanks!" Phillips was "stunned," he writes in his memoirs, The Night Watch. "We're going to mount a secret operation in the Caribbean with tanks?"

"That's right," said the colonel. "A company. Three platoons of five each, with two command tanks.

It is hard to see how the addition of tanks made the operation "less noisy." But the loss of the "guerrilla option" was a serious change in the plans. Without the ability to "melt into the mountains," the invaders had to secure and hold the beachhead-or, pushed back into the sea. There was no fallback plan. Bissell never told Kennedy. "I did not deliberately mislead the president," he said. "I didn't take the trouble to say to him that if we shift from Trinidad to the Bay of Pigs, the fallback plan becomes totally different. The guerrilla option was not an option.

(3) Jake Esterline was interviewed by Jack Pfeiffer on 10th November, 1975.

Jack Pfeiffer: I have a question, and it is what was Pawley's relation to this whole operation... and your relation with Pawley seems to have been quite close, too.

Jake Esterline: I think it was a hangover relationship from the things that Bill Pawley had done as quite a wheel with a number of very senior people during the Guatemalan operation ... that they felt that Bill, who had been very closely tied into Cuba ... that he was a very prominent man in Florida... that there were a lot of things that he might be able to do, in the sense of getting things lined up in Florida for us... and also his ties with Nixon and with other republican politicos. I used to deal with him quite a bit before.... From my point of view, we never let Bill Pawley know any of the intimacies about our operations, or what we were doing. He never knew where our bases were, or things of that sort. He never knew anything specific about our operations, but he was doing an awful lot of things on his own with the exiles. Some of the people that he had known in Cuba, in the sugar business, etc. I guess he actually was instrumental in running boats and things in and out of Cuba, getting people out and what not, and a variety of things that were not connected with us in any way. He was a political factor from the standpoint from J.C.'s standpoint. I don't know whether Tommy Corcoran entered in at this point... I think Tommy Corcoran was strictly in Guatemala. I guess Corcoran didn't come into this thing, at least not very much.

Jack Pfeiffer: His name turns up once or twice.

Jake Esterline: Yes, I met him once, in connection with Cuba, but I don't remember who... for J.C King, but I don't remember why, at this point. It wasn't anything of any significance. My feeling with Pawley... he was such a hawk, and he was every second week... he wanted to kill somebody inside... . It was from my standpoint - we were trying to keep him from doing things to cause problems for us. This was almost a standing operation.

Jack Pfeiffer: This is what I was wondering, because Tracy Barnes, I know on a number of occasions, seemed to make it quite clear that what the Agency had to be careful of was getting hung with a reactionary label, and then at the same time that was going on, here is all of this conversation back and forth with Pawley and his visits...

Jake Esterline: Really to keep him from doing something to upset the applecart from our standpoint. In that sense, I did fill that role in part for a long time; and the net result of the thing is that Bill thinks I am a dangerous leftist today. If I hadn't been a foot dragger, or hadn't taken all these dissenting opinions of this, things in Cuba would have been a lot better.

Jack Pfeiffer: Was Pawley actually involved in the covert operation in Guatemala?

Jake Esterline: Yes, he, well I am sure he was, in a...

Jack Pfeiffer: I mean, with you as far as you...

Jake Esterline: Not I personally, but he was involved with State Department. I said Rubottom a couple of times, I didn't mean Rubottom, I meant Rusk. He was involved - especially in Guatemala with Rubottom or whoever Secretary of State was, and Seville Sacassaa and Somoza and whoever Secretary of Defense was in getting the planes from the Defense Dept., having them painted over, the decals painted over and flown to Nicaragua where they became the Defense force for that operation.

Jack Pfeiffer: I ran across some comment that he had made to Livingston Merchant.

Jake Esterline: They were good friends, and knew each other. But to my knowledge, he never had any involvement like that during the Bay of Pigs days, although you'd have to ask Ted Shackley about what they did later, because I think he ran some things into Cuba for Ted Shackley.

Jack Pfeiffer: That is beyond my period of interest. He was involved in a great amount of fund raising activity, in the New York area apparently - pushing or raising funds in the New York area - wasn't Droller involved in this too? What was your relation with Droller... were you directing Droller's activities, or was Dave Phillips running Droller...

Jake Esterline: Oh, I sort of ran Droller, except I never knew what Tracy Barnes was going to do next, when I turned my back. Droller was such.an ambitious fellow trying to run in... trying to run circles around everybody for his own aggrandizement that you never knew... but Droller would never have had any continuing contact with Pawley, because they had met only once, and I recall Pawley saying that he never wanted to talk to that "you know what" again. He was very unhappy that somebody like Gerry... he just didn't like Gerry's looks, he didn't like his accent. He was very unfair about Gerry, and I don't mean to be unfair about Gerry - the only thing is that Gerry was insanely ambitious. He was his own worst enemy, that was all.... We just didn't think that Tracy really understood it that well, or if Tracy did, he coudn't articulate... he wouldn't articulate it that well. Tracy was one of the sweetest guys that ever lived, but he coudn't ever draw a straight line between two points....

Jack Pfeiffer: What about JFK?

Jake Esterline: JFK was an uninitiated fellow who had been in the wars, but he hadn't been exposed to any world politics or crises yet if he had something else as a warm up, he might have made different decisions than he made at that time. I think he was kind of a victim of the thing. I blame Nixon far more than I do Kennedy for the equivocations and the loss of time and what not that led to the ultimate disaster. Goodwin, I just thought was a sleazy; little self-seeker, who I didn't feel safe with any secret. His consorting with Che Guevara in Montevideo had rather upset me at the time...

Jack Pfeiffer: How about McNamara did you get involved with him at all?

Jake Esterline: No.

Jack Pfeiffer: Bobby Kennedy?

Jake Esterline: I wouldn't even tell you off tape. I didn't like him. He's dead, God rest his soul.

(4) Don Bohning, Troubling questions still haunt legacy of Bay of Pigs, The Miami Herald (17th April, 1998)

Thirty-seven years later, as the Bay of Pigs fades into history, many questions have been answered by the release of long-secret documents and the increasing willingness of the few remaining central participants to talk.

But many of the answers raise other questions surrounding the ill-fated invasion of Cuba on April 17, 1961, by a brigade of 1,500 Cuban exiles trained and supported by the CIA.

Two of the most troubling, according to participants and analysts:

Was a failed Mafia assassination plot against Fidel Castro directly linked to the invasion? And, if so, did that detract from the invasion planning and execution?

Did a combination of ego and ambition cause the late Richard Bissell -- the man most directly responsible for the invasion as the CIA's chief of clandestine and covert operations -- to mislead both President Kennedy and Bissell's own planners?

Author Seymour Hersh, in his recent book The Dark Side of Camelot, a critical look at the Kennedy presidency, most persuasively raises the linkage between the invasion and an assassination plot that began under the Eisenhower administration.

Why was mission canceled? " One of Kennedy's most controversial and least understood decisions during the Bay of Pigs was the cancellation of the second bombing mission'' Hersh writes. "The assumption that Castro would be dead when the first Cuban exiles went ashore, and the fact that he was not, may explain Kennedy's decision to cut his losses. The Mafia had failed and a very much alive Castro was rallying his troops.''

Hersh quotes Robert Maheu, a former FBI agent and the link between administration officials and the Mafia for the assassination plot code-named ZR/Rifle, as telling him that "Taking out Castro was part of the invasion plan.'' Castro's murder, said Maheu, was to take place "before - but preferably at the time of - the invasion.''

The plot fell apart when Juan Orta, who functioned as Castro's private secretary and was to slip a poisoned pill into a drink, apparently got cold feet and took refuge in the Venezuelan Embassy a few days before the invasion. Orta died several years ago.

Kennedy, Hersh said in an interview, must have known by April 15 - two days before the invasion - and perhaps earlier, that the assassination plot had fallen apart and "he was in real trouble with the operation.''

The question then became, Hersh said, whether Kennedy should "take a bath by going ahead with it or take a bigger bath politically if he stops it. If he stops it he takes a tremendous hit from the right.''

Peter Kornbluh, senior analyst at the National Security Archive, a nonprofit documentation center in Washington responsible for the recent declassification of hundreds of Bay of Pigs-related CIA documents, concurs that the question of linkage between the assassination and invasion is an intriguing one.

"The degree to which it (the assassination plot) was coordinated as part of the planning and whether the President actually knew about it and factored it into the decision-making process'' is a key question, Kornbluh says.

Historian Arthur Schlesinger insisted in at least two appearances at the Miami Book Fair last November that he did not believe Kennedy was even aware of an assassination plot against Castro.

If there was a link, key CIA planners for the Bay of Pigs invasion apparently were not aware of it. Jake Esterline, the Bay of Pigs project director, says he learned of the assassination plot by accident when he was asked to approve an unexplained expenditure by the late J.C. King, then head of the CIA's Western Hemisphere division.

"I really forced my way in by refusing to pay unless I knew what I was paying for,'' Esterline said in an interview. "That got me partially briefed.''

Esterline said he was sworn to secrecy and didn't even tell Jack Hawkins, a retired Marine colonel who headed the Bay of Pigs paramilitary planning staff. Hawkins did not learn about it until long after the failed invasion.

Esterline now believes there "is no question about it... if that whole specter of an assassination attempt using the Mafia hadn't been on the horizon, there would have been more preparation'' for the invasion.

He believes "Kennedy and his group were not prepared to support the operation and if Bissell and others hadn't felt they had that magic bullet (assassination), I don't think we would have had all the hairsplitting over air support.''

Esterline has no doubt that Kennedy knew of the assassination plot.

The questions surrounding Bissell arose in the spring of 1996 at a conference on the Bay of Pigs attended by former CIA officials, brigade members and academics, following release of documents to the National Security Archive.

Those documents and later information have convinced both Hawkins and Esterline, who worked for Bissell on the Bay of Pigs, that Bissell was not leveling with them and probably was not passing on their concerns to Kennedy over such things as a change in the landing site and air cover.

Hawkins cites a recently declassified briefing paper by Bissell to the President dated April 12, 1961, that he says "proves that Bissell had agreed with Kennedy several days before the operation began to cut the air support in half.''

Bissell didn't tell Esterline and Hawkins about the decision until the invasion.

"I am sure Bissell never made it clear to the President why it was necessary to eliminate Castro's air force before the landing,'' Hawkins said. `"I gave great emphasis to this... Bissell knew what the military staff's opinion was about this need but . . . Bissell never pressed it.''

(5) Don Bohning, The Miami Herald (18th October, 1999)

Jacob Donald "Jake'' Esterline, a veteran of US intelligence services and the CIA'S project director for the ill-fated 1961 Bay of Pigs invasion of Cuba, has died at age 79. Death came quickly at midday Saturday as he collapsed of an apparent heart attack while riding in a car with his son-in-law near his home in Hendersonville, N.C.

Esterline, who spent 27 years with the Central Intelligence Agency and its World War II forerunner, the Office of Strategic Services (OSS), was a significant participant in the making of contemporary history.

In addition to his role in the Bay of Pigs, he commanded a battalion of Burmese guerrillas in a jungle war against the Japanese; was chief guerrilla warfare trainer at The Farm, a once-clandestine training school for CIA recruits at Williamsburg, Va.; headed the CIA's Washington task force in the 1954 overthrow of Guatemalan President Jacobo Arbenz; served as CIA station chief in Guatemala, Venezuela, Panama and Miami during the height of the Cold War and as deputy chief of the agency's Western Hemisphere division.

Apart from the Bay of Pigs, it was as chief of the CIA's Miami office from 1968 to 1972, that involved him most directly in Cuban affairs.

His task in Miami was to quietly complete the phase-out of the unsuccessful post-Bay of Pigs secret war against Fidel Castro - started by the Kennedy administration and known in its initial stages as Operation Mongoose - without creating a scandal that might embarrass Washington.

That meant disposing of ships and boats, terminating leases on safe houses, marinas, boat yards, relocating the CIA's Miami offices and - the most difficult task - laying off the several hundred Cubans still directly on the payroll.

''I felt a sense of obligation to the Cubans after the failure of the Bay of Pigs,'' he said, explaining in a 1995 interview why he volunteered for the Miami assignment. ``If it was going to be done, I wanted to see it done right.

''I thought, Really, my heart will always be with these people, these Cuban exiles in all these years, starting with the Bay of Pigs, and I don't want to see them cast in the cold.''

For better or worse, however, his role in the Bay of Pigs remains the event for which he will be most remembered and one that haunted him for the remainder of his life.

He had been recalled from Venezuela in early 1960 to undertake the project, which initially was envisioned as a guerrilla incursion at Trinidad, on Cuba's south coast. It eventually evolved into a full-scale invasion at the Bay of Pigs, an isolated swamp area 80 miles to the west.

Both he and Marine Col. Jack Hawkins, his paramilitary counterpart in planning the invasion, became increasingly doubtful of its chance for success. On an April Sunday, a week before the invasion, Esterline and Hawkins went to the home of Richard Bissell, the agency's director of clandestine services who was in overall charge of the operation, and told him they were quitting.

After a heated discussion, Bissell talked them out of quitting by appealing to their loyalty and warning that their resignations wouldn't stop the invasion.

''We made a bad mistake by not sticking to our guns and staying resigned,'' he said in the 1995 interview.

The invasion failed, with both Esterline and Hawkins convinced the change in landing sites had much to do with its failure, along with President Kennedy's reduction in the air cover that had been promised for the invaders.

Hawkins, in a telephone interview Sunday, recalled that Esterline, in his capacity as the invasion task force chief ``had struggled continually to persuade political authorities to provide all the support and protection necessary for a small force of Cuban exiles to be landed on the Cuban coast.

''Failing this,'' said Hawkins, "he warned his superior at the CIA that the landing could not succeed with the restrictions imposed by the president. He recommended cancellation, but his advice was not heeded. The result was a military, political and diplomatic disaster at the Bay of Pigs.''

Hawkins praised Esterline as a man ``whose dedication and abilities were recognized at the CIA throughout his long career'' and who "devoted his life to the defense of the United States.''

''Jake was a great leader,'' said Sam Halpern, a retired CIA colleague and contemporary of Esterline. "He believed in what he was doing and he saw trouble ahead at the Bay of Pigs and tried to stop the operation to no avail.''

''I had the privilege and honor of serving under him during the U.S. intelligence community's secret war against Castro communism,'' said Carlos Obregon, a Cuban-American businessman in Miami. ``He shared with hundreds of us exile Cubans a love and passion for our cause.''

Born in Lewistown, western rural Pennsylvania on April 26, 1920, Esterline attended Temple University in Philadelphia for three years then enrolled in Officer Candidate School where he was when World War II war broke out.

He was recruited into the OSS, winding up as the commander of a Burmese guerrilla battalion fighting the Japanese, and was awarded a Bronze Star for his service.

He returned to Pennsylvania after the war, finishing an accounting degree at Temple. Ordered back to active duty in 1951 when the Korean War broke out, he took up a standing offer to join the CIA.

Survivors include Mildred, his wife of 53 years; two sons, Jacob Alan Esterline of Austin, Texas; and John Esterline of Peachtree City, Ga.; and a daughter Ann Hutcheson of Flat Rock, N.C.