By the time 1990 rolled around, Bobby was quite a success in life. He had just started his own business and asked Peter to come on board as equal partners, and the business was moving in a solid direction north. But even earlier, there were seeds sown for his success first as a key member of his college baseball team (in The Brady Girls Get Married) and later as a race car driver, with several wins under his belt. Even late in the run of the original Brady Bunch, Bobby was a budding pool shark, soundly beating Mike's co-workers at a get-together.
But there were some times when the youngest Brady boy was rarely succeessful. Always the groomsman, never the groom, at jacks, jump rope, checkers ... ice cream eating contests on kiddie shows. That last one was the latest in his long line of failures and second-place finishes, and ensuring a clean trophy shelf in "The Winner."
When Cindy - the youngest - comes home with a first-place trophy for winning a park board jacks tournament, Bobby realizes what this means "I'm the only Brady sibling without a trophy." After alternately moping around the house and trying too hard to win a trophy the efforts of which ended badly Bobby seems to have finally found his niche in selling magazine subscriptions for a school fundraiser. Bobby is doing exceptionally well, but Mike and Carol decide to help him out and not tell him about it. He is announced as the winner of the contest, and Bobby's spirits have perked up considerably ... until Cindy runs into the room and, upon Bobby boasting that he's the best magazine salesman at his school, Cindy says, "No you're not. ..." before realizing she said too much. Bobby figures out what this means he didn't win anything at all on his own. He angrily tells his parents he's canceling all his magazine orders and vows to win something on his own.
A day later, his favorite afternoon TV kiddie show, "Cartoon King," is on the air, with a huge ice cream eating contest and a golden scoop for the winner. Bobby immediately enters, since he loves ice cream. On the day of the contest, Bobby is doing very well, despite the crazy rules of having to eat with your mouth and getting lots of whipped cream to boot ... but then someone finishes ahead of him. "I lost ... again." Bobby sadly sighs, as the winner (a heavy-set boy about Bobby's age) celebrates with the Cartoon King.
Bobby and his parents come home, the young tyke convinced he's a loser that nobody even wants to look at. Until he walks into the living room and sees a trophy ... well, formerly Greg's trophy, that his siblings touched up for him, all for trying his best and being the best "Bobby Brady" out there. Bobby is truly touched and humbled. Out of all the later honors Bobby would win college conference championships on the diamond and trophies on the race track, and even the civic awards during his professional career, the first trophy Bobby ever won would always remain the most special to him.
Tropes present in this episode:
- Always Second Best and Always Someone Better: Why Bobby doesn't have a trophy. What he thinks of himself when he sees that every other Brady sibling — and most likely, his parents and Alice as well — has a trophy.
- Big Eater: The ... well, overweight 9-year-old boy who wins the Cartoon King ice cream eating contest.
- Competition Freak: What Bobby becomes in his quest to win a trophy any trophy and as a result, he does worse than if he weren't playing for anything at all.
- Eating Contest: The ice-cream eating contest on "Cartoon King."
- Everyone Gets A Trophy: In an era before participation trophies were given out merely for showing up, much less the term being coined, the trophy that Bobby is given by his siblings — for being "the best Bobby Brady" — is probably the closest thing to a "participation trophy" that existed in early 1971 (when this episode was filmed).
- No Challenge Equals No Satisfaction: Bobby wins a magazine-selling subscription contest and is finally proud that he did so by his own sweat and efforts. Or so he thinks, as Mike and Carol have helped their neighbor. Bobby wasn't supposed to know ... that is, until Cindy lets slip the truth. Bobby tearfully resolves to win something on his own or he won't win at all.
- Rage Quit: Several times in this episode:
- At one point, this happens three times in succession. First, Peter beats Bobby at checkers, prompting him to flip over the gameboard. Shortly afterward, Bobby asks to join Marcia and Jan in playing a ring toss game but — when he is unable to come close to the target — he throws the rings aside and stomps away. Later, Greg decisively beats Bobby in free-throw shooting, prompting the littlest Brady boy to (literally) take the ball and go home. Surprisingly, Mike and Carol decide to let Bobby's unacceptable attitude slide, hoping the cure will be for him to win at something (rather than take him aside and tell him such an attitude is unacceptable and that winners never Rage Quit, and that he maybe should take a deep breath, take a short break from his "trying to win at all costs" frenzy and then try again later).
- After Cindy unwittingly blows her parents' ruse during the magazine subscription contest, an angry Bobby takes all the magazine subscription slips and tells his parents they won the contest before throwing everything on the floor and storming out in tears.