By Delgreco K. Wilson, MA

PHILADELPHIA, PA – The federal court ruling landed on a Friday afternoon, the kind of late-week news dump that usually signals bureaucratic machinery grinding through the offseason. U.S. District Judge Charlotte Sweeney, sitting in Denver, had just delivered a decision that sent shockwaves through college athletics: all high school class of 2022 athletes who exhausted their fourth season of eligibility this spring are eligible for a fifth season this school year.

NCAA President Charlie Baker called it “chaos.” He warned of roster upheaval, of undrafted NFL players potentially returning to campus, of a system already straining under the weight of the transfer portal and NIL now facing another structural rupture .
Baker is not wrong about the chaos. But chaos, as any economist will tell you, is also opportunity. And for one player in particular—Derek Simpson, a 6’3″ point guard from Mount Laurel, New Jersey, who just completed a magnificent senior season at Saint Joseph’s—the ruling represents something else entirely: a fifth-year windfall that could transform his professional trajectory.

The Ruling and Its Discontents

The NCAA’s plan had been tidy. The so-called “five for five” rule—allowing athletes to compete for five seasons within a five-year window—was supposed to go into effect starting with athletes who enroll in college in fall 2027. The governing body had spent years trying to establish a clear eligibility framework, one that would limit the chaos that has defined the transfer portal era.
Sweeney’s ruling blew that framework apart. In granting the preliminary injunction, she argued that athletes who had already lost a year of eligibility due to the COVID-19 pandemic or other circumstances would suffer “irreparable harm” without the option of a fifth season. She did not buy the NCAA’s argument that retroactive application of the rule would create “roster chaos” .
Baker disagreed. “Today’s rulings and the chaos they bring to college sports are exactly why it’s time to pass this bill,” he said, referencing legislation in Congress designed to provide the NCAA antitrust protection on eligibility issues .
But for athletes like Simpson, the ruling is not chaos. It is a lifeline.

The Simpson Resurgence

Simpson’s journey to this moment has been anything but linear. He began his college career at Rutgers, where he played two seasons in the Big Ten, enduring the “eye-opening experience” of guarding future NBA players and navigating the brutal physicality of the conference . As a sophomore, he was thrust into the lead guard role unexpectedly after Cam Spencer and Paul Mulcahy departed via the transfer portal. The Scarlet Knights struggled. Simpson’s shooting percentages—30.5% from the field, 28.2% from three—reflected a player trying to carry too much weight.

He transferred to Saint Joseph’s, and everything changed.

Under the guidance of Coach Billy Lange—and then, after Lange’s sudden departure for the New York Knicks, under incoming head coach Steve Donahue—Simpson transformed from a struggling high-major guard into one of the best point guards in the Atlantic 10.

2024-25 (Junior):
Appeared in all 35 games, making 22 starts
Averaged 8.7 PPG, 3.9 RPG, and 3.6 APG
Had a 2.1:1 assist-to-turnover ratio
Scored in double figures 15 times 


2025-26 (Senior):
Started all 36 games
Averaged 13.8 PPG, 5.2 RPG, and 5.2 APG
One of seven players nationally to average 13-5-5
Led the A-10 in assists per game (5.2) and free throw percentage (91.7%)
Shot 91.7% from the free throw line, the highest single-season mark in Saint Joseph’s history
Recorded 188 assists, the second-most in a single season at SJU
Named Atlantic 10 First Team, NABC All-District Second Team, and Philadelphia Big 5 Player of the Year

The numbers tell a story of a player who found his fit, his confidence, and his game. Saint Joseph’s finished the regular season 21-10 (13-5), good for third place in the A-10. Simpson was the engine.

The Portfolio Problem: A Fifth Year Changes Everything

Simpson’s decision-making in the NIL and transfer portal era must be understood as a strategic choice made under conditions of incomplete information, asymmetric power, and time pressure. He is not simply choosing a team. He is weighing short-term financial incentives, projected on-court opportunity, developmental infrastructure, exposure to professional pathways, and personal fit against long-term career risk.

Treat Simpson’s decision as a portfolio allocation problem. He balances immediate returns—guaranteed NIL compensation, a promised role—with speculative assets: brand growth, skill development, competitive success.

Before the Ruling: Simpson was a senior with no eligibility remaining. His college career was over. His professional pathway was uncertain. He would have been a mid-major star hoping for a G-League opportunity or an overseas contract.

After the Ruling: Simpson has a fifth year. He can enter the transfer portal and leverage his All-Conference credentials, his 91.7% free throw percentage, his 5.2 assists per game, and his status as one of the best point guards in the Atlantic 10.

The portfolio has changed. The risk calculus has shifted. And Simpson is positioned to be one of the biggest winners in this chaotic new landscape.

The Case for a High-Major or Mid-Major Plus Transfer

With one year of eligibility remaining, Simpson should identify a program that will provide him with maximum NIL compensation and an opportunity to compete at the highest collegiate level.

Why a Move Up Makes Sense:

Simpson has already proven he can produce against high-level competition. He spent two years in the Big Ten. He knows what it takes to guard NBA-caliber guards. He has the size (6’3″, 175 lbs) and the skill set to compete at the Power 5 level.

The Case for Mid-Major Plus Programs (Gonzaga, Memphis): These programs can offer comparable NIL compensation to many Power 5 schools, but more importantly, they can offer a clear starting role. Simpson would be the unquestioned lead guard, running the offense, playing 30+ minutes per night, and showcasing his skills for NBA scouts.

The Case for Power 5 Programs (SEC, Big Ten): These programs may offer the most money, but they also offer the most competition. Simpson would need to earn his minutes, and there is no guarantee of a starting role. However, the exposure—playing in the SEC or Big Ten, facing NBA prospects nightly—could elevate his draft stock more than a guaranteed starting role in a mid-major league.

The Steve Donahue Factor: Simpson benefitted from the guidance and direction offered by Steve Donahue, who was named A-10 Coach of the Year after assuming the helm following Billy Lange’s sudden departure for the New York Knicks. St. Joseph’s needed Simpson’s talents and skills, and the Hawks and the A-10 provided him with a perfect platform to rejuvenate his professional aspirations. Now Simpson should identify a program that will maximize his final season.

Why Simpson Is the Quintessential Winner

Simpson is not a one-dimensional player. He is not a player who dominates the ball. He is a player who makes winning plays. His assist-to-turnover ratio is elite. His free throw percentage is historically great. His defensive instincts, honed in the Big Ten, have translated to the Atlantic 10.

And now, thanks to a federal court ruling in Denver, he has a fifth year to showcase those skills on an even bigger stage.
The NCAA calls it chaos. Simpson’s future employers call it opportunity. In a system that has been defined by uncertainty, Simpson has been given the most valuable asset of all: time.

Derek Simpson’s 2025-26 season: 13.8 PPG, 5.2 RPG, 5.2 APG, 91.7% FT, Atlantic 10 First Team, Philadelphia Big 5 Player of the Year. One year of eligibility remaining.