When Dylan Holloway put pen to paper on a five-year, $38.75 million contract extension with the St. Louis Blues, he didn't just secure his financial future—he joined an elite club of Wisconsin Badgers hockey alumni who have cashed in big at the NHL level.

The 24-year-old forward's new deal carries an average annual value of $7.75 million, placing him second only to Montreal Canadiens star Cole Caufield ($7.85M AAV) among former Badgers. Not bad company for a player who was drafted 14th overall by the Edmonton Oilers in 2020.

K'Andre Miller of the New York Rangers rounds out the top three with a $7.5 million AAV, showing that Wisconsin's hockey program continues to produce top-tier NHL talent.

While the Blues struggled to a 37-33-12 record this season—good for fifth in the Central Division—Holloway has emerged as a cornerstone piece for a franchise looking to return to Stanley Cup contention. His blend of speed, skill, and two-way play makes him exactly the type of player teams build around.

Holloway's journey to this payday started in Madison, where he made an immediate impact as a freshman, earning the Dr. Joseph Coyne-Joe Pavelski Most Consistent Player award. That's high praise considering Pavelski's legendary NHL career. He followed that up with a sophomore season that saw him named a top-10 finalist for the Hobey Baker Memorial Award, a First-Team All-Big Ten selection, and Hockey Commissioners' Association National Player of the Month honors.

For Badgers fans and Blues supporters alike, this contract signals that Holloway's best hockey is still ahead of him—and that Wisconsin's pipeline to NHL stardom is flowing stronger than ever.