Most baseball parents think only about signing bonuses, NIL money, and the path to the pros — but this episode of The Most Valuable Agent with Matt Hannaford pulls you inside the real tax strategy, financial planning, and hidden money traps that shape a player's baseball career long before the big leagues.
Former pro player and CPA Steven CASERES breaks down the real financial side of baseball development — from how players are actually paid in the minor leagues, to why state taxes can quietly take six figures out of a signing bonus, to the truth about NIL money and whether young athletes should really form an LLC.
You'll learn why two players with the same signing bonus can take home dramatically different amounts depending on residency, what families must know before draft day, how MLB teams decide where to "source" payments, and why Shohei Ohtani's contract changed the landscape forever.
If you've ever wondered how money really works in baseball — behind the contracts, behind the taxes, behind the scenes — this conversation gives you the complete playbook parents never get.
Subscribe for weekly MLB draft strategy and baseball development insights.
WHAT YOU'LL LEARN
• How MLB teams actually tax and split signing bonuses
• Why residency and domicile can change a player's take-home by six figures
• How to protect your signing bonus from high-tax states
• What NIL players must know before forming an LLC
• Why Ohtani's contract was a tax masterpiece — and the loophole it used
• How minor league salary, duty days, and jock taxes really work
• The biggest tax mistakes families make during the draft
• What documents parents must keep to stay financially organized
ABOUT STEVEN CASERES
Steven Caseres is a former professional baseball player turned CPA for elite athletes. He specializes in MLB tax strategy, residency planning, NIL structuring, and long-term financial efficiency for players navigating the draft, minor leagues, and major league compensation systems.
ABOUT MATT HANNAFORD
Matt Hannaford is a 25-year veteran MLB agent and founder of Aligned Sports. He has represented Hall of Famers, negotiated blockbuster contracts, and now delivers weekly insights on the mindset, development pathway, and business of elite baseball.
CONNECT WITH MATT HANNAFORD
Instagram: https://www.instagram.com/mfhannaford/
Website: https://www.aligndsports.com/
YouTube (subscribe for weekly coaching): https://www.youtube.com/@mostvaluableagent
CONNECT WITH STEVEN CASERES
Contact: steven@gpccpas.com
#MLBDraft #BaseballTaxes #NILMoney #SigningBonus #BaseballParents #CPAForAthletes #MostValuableAgent #PlayerDevelopment #BaseballBusiness
Popular Podcasts
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
Are You A Charlotte?
In 1997, actress Kristin Davis’ life was forever changed when she took on the role of Charlotte York in Sex and the City. As we watched Carrie, Samantha, Miranda and Charlotte navigate relationships in NYC, the show helped push once unacceptable conversation topics out of the shadows and altered the narrative around women and sex. We all saw ourselves in them as they searched for fulfillment in life, sex and friendships. Now, Kristin Davis wants to connect with you, the fans, and share untold stories and all the behind the scenes. Together, with Kristin and special guests, what will begin with Sex and the City will evolve into talks about themes that are still so relevant today. "Are you a Charlotte?" is much more than just rewatching this beloved show, it brings the past and the present together as we talk with heart, humor and of course some optimism.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.