The strongest agents know when to stop pushing.

Become a leader in the sports industry through The Game Plan Sports Business Accelerator | Representing world-class athletes at ISC | $250M+ in negotiated contracts | Levelling the playing field for children through DFYJune 5, 2026

It was the day before transfer deadline day ⌛️

We were in a club training ground...and a 6-figure commission was about to go down the drain.

The player had travelled to the local hospitals to get MRI scans and the usual tests, the club photographer has already taken the signing images...but what nobody could see outside the training ground was a frantic 24-hour negotiation playing out in the background.

I was sat there translating between English and French, the agent on one side, the club on the other, brokering in the middle to hold the deal together.

The talks were tense, long, and highly adversarial. The agent argued every point, every clause, every bonus, and was barely giving an inch on any of them.

Half an hour went on whether a car would be added to the player's benefits package or not. The ordeal ended only in the painful realisation that the player didn't even have a driving licence.

Sadly, the longest part of the negotiation was the agent's fee. Over two and a half hours were spent on this, slowly moving up in quarter percentage increments. Then, when we finally agreed on the percentage, the next sticking point was the payment structure the agent wanted: not paid annually but front-loaded.

There were frequent coffee breaks, cigarette breaks, side-talk breaks. It was relentless.

We finished after midnight 🕛

Just before we finished the medical came back. The doctor had flagged a minor concern with the player's knee. A small risk, the kind that on any other day, with any other room, would have gone the player's way. The club sent it to a specialist overnight to be reviewed, and the final decision would be made in the morning.

That following morning the club walked away. The deal was dead. A 6-figure commission had gone, and the player was heading back to his old club on a fraction of the money, in a league he didn't want to be in.

After the player's agent had left, I sat with the sporting director to debrief. He was honest with me. It was a 50/50 call, and had the agent not pushed so aggressively on every single detail, the deal would have gone ahead.

There was one element in particular that concerned them. The agent had pushed hard to have the entire fee paid up front, in year 1 of a 4-year contract. They worried that because the agent had spent so much time prioritising his own fee, once he'd been paid in full, he'd push the player to move again so he could earn another commission, and they'd be left with the headache. That clause, more than any other, made them less inclined to go the other way on a borderline medical.

The agent thought he was doing the right thing by his player. He thought his role was to fight every single clause.

By the textbook, that's exactly what an agent is supposed to do.

But he had forgotten to consider the human and emotional element present in any negotiation. The animosity he created tipped the knife edge the wrong way.

Sir Alex Ferguson once said it best:

Tell me who your agent is, and I'll tell you if we're going to sign you.

💡That day confirmed something I already knew:

Negotiation isn't only about leverage. Diplomacy plays a part in closing a deal.