Much of the magic March Madness churns out every year comes from pitting small schools with names and players few people have heard of against the Dukes and North Carolinas of the world at a time when everyone seems to be watching.
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everyone → churn → time
What makes it even better is that, sometimes, those teams win.
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teams → make → ?
But the NCAA Tournament’s most darling participant, Cinderella, is finding it harder to survive and advance in the world of expanding conferences, payrolls and transfer portals.
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it → find → conferences
The 2026-27 season ushers in the era of the 76-team tournament — an eight-team expansion to a bracket in which the biggest of the big not only control the contours of the tournament, but, more than ever, can simply elbow Cinderella out of the way using the power of their checkbooks.
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biggest → usher → checkbooks
“Unfortunately, you may see an upset, but it may be harder for the smaller schools to make those longer runs in the tournament,” said Niko Medved, who was one excruciating buzzer-beater away from taking underdog Colorado State to the Sweet 16 in 2025 before he left to coach Minnesota a few weeks later.
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he → see → Minnesota
“We’ll see what the data shows here in the next 3-4 years, but I could see that scenario.”
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I → see → scenario
Teams that once wore glass slippers, like Gonzaga or Butler, long ago shed the plucky underdog label and have either turned into behemoths or hopped into conferences with them.
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that → wear → them
Others that made a splash, like St. Peter’s or Loyola-Chicago, often see their best players and coaches siphoned away by the big boys.
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players → make → boys
The only two No. 16 seeds to beat a No. 1 — UMBC and Fairleigh Dickinson — along with 2022 Elite Eight team St. Peter’s are among the three dozen or so teams that start with a disadvantage because they don’t participate in the revenue-sharing structure that now rules talent acquisition (read: winning) in big-time college sports.
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that → beat → sports
Meanwhile, the unspoken secret about tournament expansion is that it was done to afford more big-conference teams a chance of making the field and earn the millions that come with it.
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that → do → it
Their thought: The lion’s share of the 32 automatic-qualifier spots in the tournament go to smaller leagues, and the seventh- or eighth-best team in their power conferences are at least as deserving as those teams.
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team → go → teams
Not everyone agrees with that notion.
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everyone → agree → notion
“I mean, there’s eight new spots,” said Jim Phillips, the commissioner of the ACC.
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Phillips → mean → ACC
“Now, if they don’t get any of them, they don’t get any of them, but it’s not any less than what they’ve had before.”
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they → get → what
Three of the first four teams left out of the last two tournaments came from power conferences.
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teams → leave → conferences
Last year, Boise State would have made an expanded field, but so would Ohio State, Indiana and West Virginia.
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State → make → field
Conference expansion leaves fewer mid-major contenders
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expansion → leave → contenders
Meanwhile, conference expansion has plucked some of the best mid-major teams out of their leagues and into bigger ones, and they’ve been replaced by lesser programs.
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they → pluck → programs
One example: The Mountain West used to feature BYU, Utah and TCU, but all have left for the Big 12.
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all → use → 12
Some newer programs in the MWC include UTEP, UC-Davis and San Jose State.
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programs → include → UTEP
All of which means that these days, there’s a better chance of the next Cinderella looking a lot like the 2024 N.C. State team that had to win the ACC simply to make the tournament, and ended up in the Final Four; and less like that 2006 George Mason squad that came out of the Colonial Athletic Conference and shocked the world en route to college basketball’s biggest stage.
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that → mean → stage
It is the program that, in 1983 with coach Jim Valvano, essentially coined the term “Cinderella” with a run to the title that took on mythical proportions over the decades.
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that → coin → decades
Rollie Massimino and Villanova and “Danny and the Miracles” at Kansas followed shortly after, proving that massive upsets don’t all have to belong to the so-called little guys.
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upsets → follow → guys
America loves an underdog ... until it doesn’t
Then, there’s the largely unspoken question of just how beneficial a run by the so-called little guy is for the tournament as a whole.
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run → love → whole
Yes, America loves to see a UMBC beat Virginia in the first round or Florida Gulf Coast knock off big boys on the way to the Sweet 16.
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Coast → love → 16
But the only two national finals to average more than 20 million viewers over the last dozen years involved Duke (2015) and North Carolina (2017).
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finals → average → Duke
The least-watched final involved underdog San Diego State in a defensive snoozer of a game shown on CBS.
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final → watch → CBS
Realities of NIL: Those who do break through see their rosters ravaged
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rosters → break → NIL
The most telling byproduct of the name, image and likeness era might be what happens to small teams that pull off big upsets or make unexpected runs through March Madness.
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that → happen → Madness
After its trip to the Final Four in 2024, Florida Atlantic lost seven players and its coach, Dusty May.
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Atlantic → lose → players
Two years earlier, St. Peter’s made its captivating run to the Elite Eight only to see its roster and coaching staff eviscerated, led by coach Shaheen Holloway’s departure to his alma mater, Seton Hall.
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roster → make → mater
It came as the impact of NIL and less restrictive transfer rules were hitting full gear.
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impact → come → gear
“I’d say if we fell short, we’d probably be there (at St. Peter’s) another year,” Daryl Banks III told The Wall Street Journal after leaving for St. Bonaventure.
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III → say → Bonaventure
“We all talked to each other and we knew what we had to do going forward for our careers.”
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we → talk → careers
Not that all is lost.
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all → lose → ?
Even with the three dozen teams that don’t participate in revenue sharing and dozens more that don’t spend all the way to the cap, there are tons of talented players out there and plenty of schools have the resources to lure them — at least for a while.
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plenty → participate → while
But, as Washington third-year coach Danny Sprinkle said recently, there is a reason the Huskies joined the Big Ten; quite simply, the conference distributes more money to schools, which makes it easier for it to put a stranglehold on the tournament and deprive Cinderella of oxygen.
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it → say → oxygen
“Once we get a full share (in 2030), that’ll help our program immensely,” Sprinkle said.
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Sprinkle → get → program
“The disparity is just becoming wider by the day.
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disparity → become → day
It’ll be interesting to see in the next five, seven, eight years, what that disparity is.”
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disparity → see → years
The Aporia
