In 1989, now aged 36, he took on the young power-punching Jamaican-Canadian Donovan (Razor) Ruddock. Smith's own punch power was still evident as he decked Ruddock hard in the 2nd round, but seemed to punch himself out trying to finish Ruddock, who was a crafty survivor. The next few rounds saw Smith tire, as Ruddock's youth and power overwhelmed him, knocking him clean out in the 7th round for the full 10 count. Ruddock would go on to become a star and feature in several high-profile fights. Smith's career appeared to be over. He announced his retirement after the loss and said he would now pursue politics.