That night, 17-year-old Dele Alli could hardly believe his eyes when he saw a Manchester United transfer representative.
As a standout player in Milton Keynes Dons' youth team, he had been in contract negotiations with the club. However, their offer was a mere £2,000—a figure far below what players of his caliber typically earned. It felt like an insult.
To pressure him into signing, the club let his contract expire, believing they held the upper hand. Their reasoning was simple: as a free agent from an obscure club, with no professional experience, who would take a chance on him? Confident that no one would swoop in first, they assumed Alli would have no choice but to accept their terms.
But they had miscalculated. Someone had taken an interest in Alli—Manchester United. And now, with a top Premier League club showing interest, everything had changed.
Rumors swirled that United's transfer representatives had visited his home, and before he knew it, they were sitting across from him, contract in hand. When they explained their intentions, Alli could hardly contain his excitement. He nearly signed the contract on the spot without even reading it. Going from a lower-division youth team to Manchester United's academy was like jumping straight to the top. Even if it meant accepting a pay cut to £1,000 a week, he wouldn't have hesitated.
But United wasn't a stingy club. They offered him a £5,000 weekly salary and a promise to focus on his development. Alli was ecstatic. By the time Milton Keynes Dons realized what had happened, their prized youth talent was already settled in the dorms at Carrington. Their chairman could only watch in regret.
When Tiger King heard about it, he found the whole situation amusing. "With a chairman that clueless, even the best club would go under."
After Woodward's successful first move, Tiger King was in high spirits. While he wasn't entirely fond of Woodward's "money-first" management style, he had to admit—the man was a business genius.
In just one night, Woodward had sealed the deal, securing Tiger King's first transfer.
Coming from the future, Tiger King knew exactly what kind of player Dele Alli would become. In the years ahead, Tottenham Hotspur would sign him, and alongside Harry Kane, Eric Dier, and Son Heung-min, he would help ignite a youth-driven revolution in English football. At his peak, Alli's market value would soar into the hundreds of millions.
But now? He was a free agent. Manchester United had just signed him for nothing. With £50 million still left in his transfer budget, Tiger King's eyes gleamed.
Time to buy more talent.