Since his first pro match on October 10, 1999, Diablo has taken on all challenges. He has faced wrestling veterans from every major league including WWF Ham 'n Egger Jeff Libolt, WCW's Tagteam The Power Company, and Devito of ECW's "Da Baldies." Diablo has also defeated great new independent stars such as Sledge, JP Black, Shockwave, and "Mr. Spotlight" Jeff Starr.

In 2001, "The Puerto Rican Nightmare" had sought Kenny Casanova for spiritual guidance, and The Founding Father Of The First Church Of Foolishness swore that he would do his best to bring this fine young talent, to "The Cloud Nine" that is World Championship gold. Kenny really believes that he can take this sinner, and turn him around, and if Diablo is willing to trade his Long Island Ice Teas in for Kool Aide -there is definite potential. Before each match, Kenny and The Nightmare, say a prayer, for their next opponent. Kenny has dubbed Diablo his official "Puerto Rican Deacon" and together they will pass on the Casanova's message of sweetness.

Diablo Santiago has really trimmed down and gotten into the best shape of his career in 2003. Diablo has been taking on all challenges. He has been facing wrestling veterans such as former WWF performer Jeff Libolt, ECW's "Mad-dog" Mike Bell, Dean and Dave of WCW's Power Company, and Tony Devito of ECW's "Da Baldies." Also, independent up and coming stars such as Sledge, JP Black, Shockwave, Jeff Starr, and Chip Stetson.

In late 2002, this thug, from 174th street in the Bronx, New York has put aside his singles career to form the Tag Team known as "The Outcast Killas" with Oman Tortuga. 

The Outcast Killers have decided to make life a living hell for Jeff Starr, after Starr defeated Santiago in the TSW Heavyweight tournament. After an attack on Starr by The Outcast Killers, Shockwave, The TSW Cruiserweight Champion appeared for the save. Now The Outcast Killers are in a heated feud with "The Lady killers" (Starr & Shockwave.)