In the short story "Winter Dreams" by F. Scott Fitzgerald, the protagonist Dexter Green comes from a middle-class background but aspires to rise in society. The story tells of Dexter's business success as well as his off-again on-again relationship with a wealthy socialite named Judy Jones.

Fitzgerald focuses on Dexter's relentless ambition just a few paragraphs into the story as he describes Dexter's "winter dreams." Although Dexter at the time is merely a caddy, he envisions himself as a brilliant golf champion who always wins matches, sometimes "with laughable ease" and sometimes coming up "magnificently from behind." He also imagines himself stepping out of an expensive automobile and meeting Mr. Mortimer Jones, Judy Jones's father, as an equal at the golf club. While there, he gives an imaginary "exhibition of fancy diving from the springboard of the club raft."

The next indication of Dexter's ambition in the story is when he quits caddying. Rather than behave as a servant and carry eleven-year-old Judy Jones's golf clubs, Dexter resigns from his position on the spot.

Fitzgerald continues to highlight examples of decisions Dexter makes with the goal of his "winter dreams" in mind. For instance, he passes up studying business at the local state university for an opportunity to study at an older, more prestigious eastern university. After college, he avoids the temptation to become involved in the buying and selling of bonds or other traditional business pursuits like his peers and instead buys a laundry business. He not only works hard, but also specializes in cleaning certain types of clothes to cater to the rich. As a result, while he is still very young he becomes rich and a member of the golf club at which he had once caddied.

The author also describes that while Dexter is still at university he affects the dress and mannerisms of young men he meets who are born into wealth. This makes it easier for him when he begins to pursue a relationship with Judy Jones. His ambition also extends to a marriage with Judy Jones, so much so that he is willing to drop his fiancé, Irene, when Judy accepts his proposal.

It is clear from the beginning that Dexter Green plans to leave his humble beginnings far behind him. Rather than relying on his father, who owns a grocery store, for an allowance, young Dexter gets himself a job. He is not the type of young man to sit around and leave fate to decide how his life will go.

He is earning $30 a month being a caddie for golfers at the Sherry Island Golf Club. He does his job admirably, and is considered by many to be the best caddie at the club.

Everything that Dexter does is strategic—even his sudden decision to quit his job is far from random, but based on a change of heart after the arrival of Judy Jones. His strong feelings for Judy make him realize that being a caddie may not create an impression that will allow him to succeed.

The fact that he expresses determination to go to a prestigious East Coast colleg to get an education also contributes to setting Dexter up as an ambitious young man. Once his education is behind him, our ambitious protagonist, who is still in his early twenties, acquires a loan which allows him to set up a business.

Once again, Dexter is not a man content to sit back and wait for good things to happen to him. He is an ambitious go-getter who has the brains and the determination to go far.

F. Scott Fitzgerald’s story traces Dexter Green from adolescence into adulthood. The author uses considerable detail in building the portrait of an ambitious boy who ties his dream of future success to moving away from the small town where he grew up. For the teenager, ambition is shown in the details regarding his having a job, which is a caddy at the golf course, and the way he performs this job.

Dexter seems determined not only to earn some money but also to make an impression of diligence and energy in carrying out his duties. As he grows up, he shows that he values education as a stepping stone to achieving his goals. One factor showing this aspect of his ambition is his decision to go to college. Even further, Dexter also decides to apply to an elite, East Coast private school.

Dexter is shown as a boy who always strives for more. Ironically, this striving sometimes involves taking an unpopular or unconventional step. While he values his earnings and reputation at the country club, he also realizes that carrying clubs for the members puts him in an inferior social position. Dexter’s abrupt decision to quit his job shows that he is willing to take risks and values his independence, which are also qualities associated with ambitious people.

As mentioned above, Dexter was only fourteen but renowned as the best caddy there ever was. He was so diligent at his job that he never lost a ball, causing all golfers to prefer him over every other caddy. In fact, his 30 dollar monthly salary was unheard of in his town. He opts out of attending the State University and instead chooses to attend a well known one so that he can mingle with the affluent because he wanted what they have. At only twenty three years of age, Dexter took out a loan against his college degree so as to invest in a laundry business partnership. Even though this business was small, Dexter devoted himself to learn how to handle linen without causing shrinkage and within no time, every wealthy golfer sought his service. Dexter’s business acumen propelled the expansion of the business and he opened five branches across the city and also ventured into the lingerie business. He did all the above before attaining the age of twenty seven.

At fourteen, Dexter is such a good caddy that all of the golfers request him more than any other caddy. He has many "winter dreams" of a bright, successful future. When Judy Jones makes him feel inferior, however, he quits his job and decides he must make something of himself. He goes to a prestigious college back East and becomes a successful business through hard work. He learns everything he can about the cleaning trade in order to be the best he can. He improves his manners and the way he dresses to be able to fit into the world of money. He has a vision of creating a perfect life in order to have the things that the wealthy men he used to caddy for had. Dexter was not lacking in ambition and achieved the success he thought would make him happy.

In "Winter Dreams," what indicates that Dexter is an ambitious young man?

Dexter shows his ambition by getting work as a caddy at an upscale country club. He sees this job as an opportunity to rub shoulders with the wealthy social elite, people whose glamorous lifestyle couldn't be any more different from his own. Dexter hails from an ordinary lower middle-class background and it's clear that he's anxious to escape his humble origins and achieve fame and fortune. He knows that someone like him needs connections if they're to get on in life, and so what better way to make those connections than by mixing with the kind of people who can open the doors of opportunity.

As indeed they do. For the connections that Dexter's able to make at the country club allow him to become a successful businessman, certainly far more successful than his old man ever was.

In "Winter Dreams," what indicates that Dexter is an ambitious young man?

Dexter from this Fitzgerald short story is much like the author's most famous character, Jay Gatsby.  They are both from Minnesotan families and long for a better, glamorous life away from their upbringing.  Dexter begins working at a young age, showing his ambition. And, he knows that caddying for rich golfers is no way for him to escape his tedious life; so he refuses to caddy for a little girl.

Another example of his ambition is his willingness to pass up a sure thing (a business course that his dad could have paid for) in order to pursue a more prestigious education out East. Just like James Gatz, Dexter makes a plan for his future early on and successfully carries out the business part of it (if not the personal part).

In the short story "Winter Dreams," what details indicate that Dexter is an ambitious young man?

In F. Scott Fitzgerald's short story "Winter Dreams," there are many details which indicate that the protagonist, Dexter Green, is ambitious. At the opening of the story, we discover that Dexter's family is solidly middle class and that his father owns a moderately successful grocery store. Dexter caddies for golfers at the local country club, but only for extra money.

In the first section of the story, Dexter creates wild imaginary stories that feature him playing golf with the rich men at the country club and driving an expensive car. Later, when he leaves for college, he chooses to attend an "older and more famous university in the East"—probably Yale University—though does not have a lot of money while he is there. The story explains that Dexter "wanted not association with glittering things—he wanted the glittering things themselves." This distinction is important since it tells us that Dexter wants to be wealthy and powerful, and not just be associated with the wealthy and powerful.

As an adult, Dexter owns a string of successful laundries and makes more money than other young men. This success allows him to finally access the "glittering things" he so desires. Of course, one important example of his ambition is his pursuit of Judy Jones, the wealthy and beautiful young woman who represents all that Dexter desires. Dexter's frequent attempts to possess her through marriage constantly fail. It is no coincidence that Judy is often described as being "golden" or dressed in expensive "gold" clothing; her character is symbolic of the wealth and power that fuel Dexter's ambitions. Ultimately, though Dexter becomes incredibly wealthy, he remains unhappy and disillusioned because he cannot "own" Judy.