Winchester had a sister named Honoria (pronounced ah-NOR-ee-uh), and a brother named Timmy who died when Charles was very young. In another episode, it was revealed he had a nephew named Felix, although it is not made clear if this is Honoria's son or another sibling's. In another episode, he made a tape-recorded message in which he mentioned a cousin, Alfred, making two provisions to his will: that his mother not use his shares to vote for Alfred and that Honoria receive his butterfly collection instead of "cousin Alfred".
As presented in the series, he is tall, stocky, and losing his hair, and speaks in a Boston Brahmin accent. He also suffers from a bad back.
Once Winchester arrived, he found the conditions appalling compared to the comfortable life he enjoyed at Tokyo General. Although his arrogance made a poor first impression, Winchester proved his surgical expertise when he performed a delicate heart operation on a ventricular aneurysm which the other doctors were unfamiliar with.
When it was learned that Major Burns would not be returning to the 4077th, Colonel Potter asked to have Winchester permanently assigned to the unit. This granted, first Radar O'Reilly, then Potter, broke the news to Winchester. He was shocked at first, and attempted to bribe and threaten Potter, but his pleas fell on deaf ears from Potter who threatened to have him arrested for insubordination. Very reluctantly, he moved into Burns' former quarters with Pierce and Hunnicutt, declaring his plans to use family influence to transfer back out.
When the first major rush of wounded arrived, Winchester found himself in over his head once he began operating, taking three or four times as long to finish his operations as his fellow surgeons. He learned that his slow, methodical surgery was unsuited to the gross number of patients he had to operate on, as well as the long hours into the early morning. As a result, he was forced to learn to perform "meatball surgery" from his new colleagues in order to be efficient. (He eventually made an effective transition, even criticizing other visiting surgeons if they operated slowly.)
Winchester felt humiliated at any assistance to improve his efficiency and alienated himself from the rest of the camp with his arrogant, self-centered, and at times, cold persona. He did, however, prove to have a sense of humor and a clever wit, which were not above pranks.
Winchester was the final new regular character added to the show, and the resultant ensemble remained intact for the remaining six seasons of the show's run.
Another similarity between the two characters was their tendency to venture into the occasional get-rich-quick scheme, with disastrous results. Burns fell victim to phony stock tips, rumors of a gold strike near the camp, and a fraudulent betting pool he set up for a baseball game he had already heard on the radio. Winchester tried to make some fast money by buying up Army scrip at a discount, intending to trade it in and keep the difference as his profit, but was outwitted by Pierce and Hunnicutt. He also rigged a mouse race by feeding amphetamines to Radar's pet mouse so that the 4077th staff members could win the bets they had placed, but the truth was exposed and everyone had to pay back their winnings.
Unlike Burns, Winchester was a superior surgeon whose obvious, natural skills indicated earlier on that his intelligence was superior to that of his predecessor, giving Winchester an advantage in his clashes with Hawkeye and B.J. that Burns had lacked - they could not seriously criticize him as a doctor, and he was quite capable of being as sneaky and underhanded as they were, at times even more so.
In stark contrast to Burns, Winchester did not feign adherence to military regulations. He didn't pull rank with the other camp members nearly as often as Burns did, nor did make any effort to force Hawkeye or B.J. to conform to proper military behavior. He never tried to get his colleagues in trouble by reporting their antics to General Clayton or General Mitchell, and even took offense once when Hawkeye and B.J. wrongly suspected that Winchester was secretly sending damaging reports about Potter to his superiors, saying that were no spies in his family (though they would, on occasion, hire them).
Winchester was usually unimpressed by the authority of superior officers, with the exception of Potter. Whereas Burns would shamelessly suck up to them, Winchester would not. He was not scared of Col. Flagg, in contrast to Burns. He even risked an insubordination charge once when a visiting Colonel unfairly berated Hawkeye, B.J. and Margaret for their nonmilitary behavior, Winchester stood up for his colleagues, explaining to one of them in front of the Colonel that it's against protocol that a superior officer be told he was inferior. Burns would never have behaved in such a manner in defense of the others, especially for Hawkeye and BJ.
One final difference between the two was their attitudes towards alcohol. Where as Burns was a teetotaler who chastised his colleagues for their drinking, Winchester would often drink regularly with the other officers in the Officers Club, and would even imbibe some of Hawkeye's moonshine on occasion. He also had a fondness for fine wines and brandies, and would sometimes take advantage of circumstances to procure a supply for himself.
Another incident where Winchester was happy to have Hawkeye around was after a staff switch where he and Nurse Bigelow went to the 8063rd for a week, Winchester absolutely loathed Pierce's replacement, Captain Roy Dupree (George Lindsey), so much so that when he returned to the Swamp, Winchester was absolutely overjoyed to see him, and welcomed him back with open arms. Winchester and B. J. hated him so much that the two swampmates tricked Dupree into riding Col. Potter's horse, Sophie. Potter, who had been considering having Dupree transferred (because 'we can always use an extra chest cutter'), angrily rescinded the offer of transfer. Winchester did, however, enjoy the company of Major Houlihan's old friend and classmate, Captain Lorraine Anderson (Marcia Rodd) who had come along for the week.
He often displayed his fear of war and the question of life after death, and in one poignant episode, Winchester deliberately set himself at the front line after finding a bullet hole in his hat, meaning he had missed death by inches. Ignoring an order by Col. Potter to return to the camp, he desperately questioned a patient who was mortally injured in a fruitless attempt to discover what might await anyone close to death. Winchester asked what the patient was experiencing, but the patient's only semi-comatose response was that he could smell bread.
Winchester took his nominal second-in-command position far less seriously than Frank Burns ever had; on the rare occasions when Potter left him in charge, Charles usually let the camp go through its paces and everyone have what they wanted as long as Charles in turn got what he wanted (usually a personal favor, or simply time alone). In addition, on occasions when Hawkeye was left in charge for varying reasons (once including Winchester's own insistence that he was not up to the task), he did not take offense. (However, the first time he was camp CO, though, he went overboard on ordering creature comforts, only to be put in his place by a returning Col. Potter.)
Winchester always took his personal standard as a physician very seriously, even egotistically painting himself to be the best surgeon in the room, setting himself up for humiliation, throwing a temper tantrum twice: once, when a female surgeon (played by Mariette Hartley) proved herself his equal, and when a younger surgeon taught Winchester a new surgical technique. In one episode he derided local Buddhist Korean physicians who had come to see the methods used by the 4077th, making snide comments on their traditional methods and calling them Moe, Larry and Curly, thinking only one spoke English (he tells them these are respected wise men in America). After one practitioner cured Winchester of a back injury using acupuncture, he apologized deeply, whereupon one quipped, "Not bad for Three Stooges, eh?" Bemused by his experience, Winchester said he felt "knitted and purled". Winchester was often stubborn, once when he had a severe toothache, he refused to admit his tooth hurt. He continued drinking pain killer medication even in plain view of Major Houlihan. Finally, Colonel Potter ordered him to eat a spoonfull of ice cream in the mess tent. Potter shouted, "present spoon!!" Winchester managed to hold his scream until he left the tent.
His medical high standards came into play when he had to make an inspection of a neighboring Army unit in a poor mood and unwilling to concede the realities of life at the front. Its standards of cleanliness were so low that he gave it an approval rating of "zero" on the grounds he couldn't give it anything lower.
Winchester got a dose of humility when he became addicted to amphetamines to compensate for being tired all the time. He suffered a meltdown during a race between one of Radar's pet mice (named Daisy) and a mouse owned by some wounded Marines (Radar's mouse won because Charles fed it some amphetamines, which came out along with his secret). Pierce and Hunnicutt examined him and his locker and realized what he was doing and gave him a stern talking-to. Literally sick and embarrassed at his failing, Charles ended the episode rather cold, sharp and snippy, or as Hunnicutt put it, "perfectly fine."
He once found himself at war with the whole camp in one episode, when his family was sending newspapers from back home, and the isolated camp personnel were anxious to read his papers. When he noticed one missing, he accused someone in the camp of stealing it over the PA system, thereby insulting the whole camp. The pranks grew steadily out of hand and Winchester was on the verge of dropping the whole mess tent on the lunching camp when Col. Potter stopped him, pointing out that there had not been a newspaper that day due to a wildcat strike. Potter forced a humiliated Winchester to apologize over the PA, just as he had insulted them.
Though nowhere near as flirtatious and lustful as Hawkeye Pierce, Winchester, being unmarried, was not immune to desire for female companionship. His surgical knowledge and gentlemanly demeanor initially attracted Margaret Houlihan, and several overtures were attempted for the two to end up in at least a dating relationship. However, the chemistry between the two was not there, and Charles and Margaret maintained a platonic relationship for the remainder of the series. On occasions when Charles did date, the following occurred:
Once during the series, Winchester found a British officer who had similar Blue Blood taste, even becoming envious that the man had more experience and loftier standards and experiences than him. At the end, Winchester was taught a lesson when the man smugly told him that he had those experiences as a butler's son on a wealthy English estate, and insinuated that Winchester's repeated attempts to try to one-up him were ego and masochism (all to Hawkeye's delight, who bursts out laughing.) Winchester was initially offended but attempted the lesson in humility with some self-deprecation.
Furthermore, he engaged in a few pranks, including one episode where Colonel Flagg invaded the camp and Charles planted 'evidence' to lead him on a wild goose chase, wherein Flagg became convinced that conspirators were meeting in the guise of a bridge game. "The 'conspirators' included Hawkeye, Colonel Potter, the Mayor of Uijeongbu, and the chief of police, who were not amused at Flagg's accusations. When Hawkeye questioned Charles, Charles demurely stated that he wasn't the type to pull pranks, unless it was good for a laugh. He also once used a dummy grenade to clear out the Officer's Club so he, Hawkeye, B.J., Klinger, and Soo Lee could get a table. In practical jokes, Winchester was a master manipulator.
Despite Winchester stating that he didn't care about the Red Sox - he considered baseball a "lower-class sport" - he became a baseball expert when he placed a huge bet on the Brooklyn Dodgers not blowing their 13-1/2 game lead during the 1951 season, only to lose all his money during the three-game playoff, when Bobby Thomson hit his famous pennant-winning home run.
In another episode, Hawkeye and B.J. tried to get the Otto Preminger film The Moon is Blue which, because of its supposed "lurid content", had been banned in Boston. Winchester chuckled at this notion and tries to give them a discreet warning to keep their expectations in check by telling them Boston would ban Pinocchio.
Several hours later, Charles was devastated to discover one of the final patients in triage was one of the musicians. Charles asked the corpsman if any other prisoners had survived, but was informed that the dying man was "the only one that made it this far." Charles, sadly and bitterly, remarked, "He wasn't a soldier. He was a musician."
Retreating to his tent, Charles attempted to find solace in a record of Quintet for Clarinet and Strings but after only a few moments of listening, he wordlessly yanked the record off the phonograph and smashed it. The armistice to end the Korean War was signed soon after, and at the 4077's last supper, Charles announced: "I will be head of Thoracic Surgery at Boston Mercy Hospital, so my life will go on pretty much as I expected... with one exception. For me, music has always been a refuge from this miserable experience... now, it will always be a reminder."
Margaret had used her connections to arrange Charles' position at Boston Mercy. At first, Charles refused the help, expressing that he wanted a position based on his own merits. His confession, at the supper, that he would accept the position was a pleasant surprise to Margaret, whom he thanked just before leaving, giving her a book she treasured that he'd initially refused to let her take back to the States with her, as it was part of a collection of books.
With the 4077th packing up and the personnel moving out to return home, Charles left the camp with Rizzo in the last remaining vehicle: a garbage truck. When Rizzo pulled up in the truck, he apologized, "I hope you don't mind riding in a garbage truck, but it's the last vehicle I got", to which Winchester replied, "Not at all. What better way to leave a garbage dump!" Charles bade Hawkeye and B.J. farewell, bowing and uttering his trademark, "Gentlemen", in his typical Boston drawl, retaining his dignity to the end. Yet Winchester emerged from his experiences as a surgeon at the 4077th a changed man, and returned home a more caring, open-minded human being despite his upper class facade. Before climbing aboard the garbage truck, Charles uttered these words of farewell to Hawkeye and BJ: "I want to thank you both. You've... made me realize what going home is all about."
(often used as acknowledgement to others when departing the room, but he always added "Corporal" when referring to either Radar or Klinger.)
(arguing with Col. Potter) "Know this. You can cut me off from the civilized world. You can incarcerate me with two moronic cellmates. You can torture me with your thrice daily swill, but you cannot break the spirit of a Winchester. My voice shall be heard from this wilderness and I shall be delivered from this fetid and festering sewer!"
(to Col. Baldwin) "I've groveled! I have endured your insufferable cribbage playing! I have kissed your brass! But I WILL NOT, even for a return to that pearl of the orient Tokyo, lie to protect you while destroying a friend's career!"
"I do one thing, I do it very well, and then I move on."
"Thank you, no"
(Acknowledging Klinger's dedication) "He is the Michelangelo of deviants!"
"I have no friends in Asia, only in Newport. A few in Martha's Vineyard."
(explaining how he stays dry, during a heat wave) "First of all, I don't sweat, I perspire... and second of all, I don't perspire."
"Pierce, you remind me of a Cocker Spaniel I once had. He, too, was cheerful in the mornings. So I gave him to a family of immigrant Japanese, and they ate him."
"I've heard snappier comebacks from a bowl of Rice Krispies."
(to Col. Flagg) "I will criticize Pierce, I will ridicule him, I will even humiliate him. But I will not spy on him!"
"Mr. Williamson - there is no life after Boston!"
(returning from a night treating wounded soldiers, in an overturned truck) "Be it ever so crumbled, there is no place like home."
(to a raving AWOL Italian soldier) "My good man, I have better things to do than to stand here and listen to someone make no sense in two languages!....(after being told their next meeting won't be as pleasant) "Well, this one has been enchanting, let me assure you. I can hardly wait for the next one. I shall be anxiously counting the decades!"(after which Charles, without thinking, walks onto a floor of wet cement in the O.R.)
(taping a message home to his parents) "Father, you must know someone influential who can get me out of this cesspool. Talk to Senator Griswold. After all, you paid good money for him!"
"Finally, a peaceful moment to conclude this tape. The would-be lothario Pierce is fast asleep, and the 38-hour day is done. Now, Mother and Father, I will put this as eloquently, and succinctly, as possible....(attempts to pour a cup of tea, but finds a rubber chicken in the pot instead) Get me the hell out of here!!"
On screen Plot Holes:
Winchester's other interests include: