Institutional Loyalty vs Premier League Reality: The Adam Underwood Dilemma at Leeds United

Leeds United’s return to the Premier League is a high-stakes moment in the club’s history — a time when shrewd decisions off the pitch are just as critical as performances on it. Amid this pressure, one decision stands out as both bold and potentially dangerous: entrusting Adam Underwood with a leading role in shaping football operations.

1. He’s a Career Administrator, Not a Proven Football Operator

Underwood has spent the bulk of his career in youth development and administrative roles. He deserves genuine credit for helping Leeds attain Category One academy status and building a productive youth pipeline. But developing teenagers and managing Premier League-level transfers are two entirely different skill sets.

A Sporting Director (or football advisor) needs to manage agent relationships, navigate complex contracts, identify undervalued talent in competitive markets, and support the head coach with experienced player recruitment. Underwood has little to no track record here. That’s not a knock on his intelligence — it’s just a mismatch between experience and the role’s demands.

2. His Appointment Looks More Like Internal Convenience Than Strategic Planning

From a systems perspective, appointing internally can maintain continuity — but it can also be a red flag when a club needs radical ambition. After  Victor Orta was released from his duties all hell broke loose at Leeds, demonstrating implications even to this present day of issues regarding transfers and contracts he made; leaving the new regime to sacrifice players that weren’t up to standard to wear the white shirt either selling or loaning out passengers that were brought into Leeds. Then following onto his successor Nick Hammond, Leeds seemingly filled the role with someone brought in to clean up the mess and change the trajectory of where the Whites were heading.

For a club trying to survive in the Premier League, appointing a Sporting Director should be a surgical, high-precision decision, not an HR shuffle. Underwood may have institutional knowledge, but that doesn’t automatically translate into the elite network or judgment Leeds need at the top level.

3. Ideological Rigidity: The B-Team Controversy

Underwood has gone on record advocating for B-teams in the English football system — an unpopular and divisive stance. While this might seem like a small side issue, it suggests something larger: a willingness to push controversial models that alienate fans and lower-league clubs.

Being a football advisor isn’t just about internal operations; it’s also about representing the club in the broader ecosystem. Taking positions that isolate Leeds from the rest of the football pyramid — especially in loan markets or EFL relations — could hurt long-term strategy.

4. No Proven Eye for Senior Talent

A key duty of any Sporting Director is knowing which players to buy, sell, or retain — and how to build a competitive squad within financial constraints due to PSR. Underwood’s strength lies in youth systems and administrative structure — not in talent identification, market valuation, or first-team squad building.

One thing that is a positive was renewing Sam Byram’s contract at Leeds. This feels an honouree contract for someone who has been under the radar over the last two seasons at Elland Road with the impact he has given; despite injuries he has suffered at Leeds, as well as other clubs he has played for elsewhere.

5. This Is the Worst Possible Time for Learning on the Job

Let’s be clear: every Sporting Director has a first season. But not every first season comes during a Premier League return, when TV revenue stakes are sky-high, expectations are massive, and squad depth for pure quality is thin.

Leeds don’t have the luxury of a transitional season to let Underwood learn the ropes. Every mistake — a poor signing, a delayed negotiation, a misjudged contract — could cost the club tens of millions. If the job goes wrong, there may be no second chance.

Final Thoughts: Good Man, Wrong Time?

Adam Underwood is not an incompetent figure — far from it. He’s respected within Leeds, loyal to the club, and has played a huge part in building one of the country’s most productive academies.

But from a risk analysis perspective, this feels like a high-leverage experiment at a fragile moment. Leeds need a deal-maker, a squad strategist, and a pressure-tested football executive. What they’ve chosen instead is someone who’s been excellent at building systems, not navigating top-tier storms.

If Underwood succeeds, he’ll prove many people wrong. But from where I stand, this appointment is less a bold move — and more a risky roll of the dice.