What Players REALLY Keep: The Shocking Truth About MLB Taxes & NIL Money
Most Valuable Agent with Matt Hannaford
Release Date: 11/26/2025
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The Biggest Gamble of Austin Riley’s Career.
Most Valuable Agent with Matt Hannaford
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Stop Being the Fixer - How to Truly Empower Your Son’s Baseball Career
Most Valuable Agent with Matt Hannaford
Most dads step into their son’s baseball journey believing they need to fix, protect, analyze, and carry the weight of every result. It comes from love — but it often creates the exact pressure, resentment, and distance they’re trying to avoid. In this solo episode of The Most Valuable Agent, MLB agent Matt Hannaford reframes one of the most misunderstood roles in youth baseball: the role of the father. Your son doesn’t need you to be the hero of his story. He needs you to be the guide. Matt breaks down why trying to “save” your son from failure actually limits his growth, how...
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Most Valuable Agent with Matt Hannaford
Most parents want the roadmap — the blueprint that turns a young athlete into a confident, motivated, successful player. But very few people have lived all sides of the journey. In this episode of The Most Valuable Agent, Matt sits down with someone who has: Kevin Griffin — • Head Softball Coach at Belhaven University • Associate Athletic Director • Former college & semipro baseball player • And father of MLB’s top minor league prospect, Connor Griffin Kevin brings a rare perspective: parent, coach, recruiter, evaluator, and someone who has navigated the pressure,...
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The Truth About Baseball Development (According To MLB Scouts)
Most Valuable Agent with Matt Hannaford
Most travel ball parents focus on the wrong things — more reps, more tournaments, more lessons, more mechanics, more “fixes.” But in this episode of The Most Valuable Agent, MLB agent Matt Hannaford brings together two of baseball’s most respected insiders to reveal what actually develops a player: • Hugh Quattlebaum — former MLB hitting coach, coordinator, and father of three boys in the youth baseball world • Gus Quattlebaum — Vice President of Scouting Development & Integration for the Boston Red Sox Together, they break down the essential (and often misunderstood)...
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3 Steps To Fix the Parent-Player Relationship In Youth Baseball
Most Valuable Agent with Matt Hannaford
Every parent watching their son strike out in the bottom of the ninth has felt that surge of frustration — not because of the strikeout itself, but because of the unspoken expectations they carry. Expectations about effort. About performance. About gratitude. About results. But here’s the problem: most parents never say these expectations out loud — and because of that, players don’t know the rules, don’t know the standards, and don’t know how to win. The result? Disappointment for parents, defensiveness for players, and a breakdown in trust that lasts far beyond a single...
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Most Valuable Agent with Matt Hannaford
Every travel team promises “elite competition,” “national exposure,” and “top-tier development.” But when you're the parent making decisions, the real questions are much simpler — and far more important: What actually serves my son’s long-term future? What protects our family’s time, budget, and sanity? In this episode of The Most Valuable Agent, MLB agent Matt Hannaford breaks down the four essential questions every baseball parent must ask before choosing a travel team. You’ll learn how to evaluate a program’s philosophy, how to separate hype from real development, how...
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What Players REALLY Keep: The Shocking Truth About MLB Taxes & NIL Money
Most Valuable Agent with Matt Hannaford
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...
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MLB GM Secrets: The Part They Don’t Share with Fans
Most Valuable Agent with Matt Hannaford
Most parents only see the rankings, the showcase stats, and the hype — but this episode of The Most Valuable Agent with Matt Hannaford pulls you inside the real world of MLB draft strategy, where decisions are made long before a player ever hears their name called. Former Minnesota Twins GM Thad Levine reveals what truly drives baseball scouting insights today, from how MLB teams evaluate players beyond raw tools to why character, adaptability, and leadership quietly determine careers. You’ll hear how clubs weigh high school vs. college talent, why certain pitchers carry heavy risk...
info_outlineMost 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
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