Pro Wrestling Guerrilla
Sky then joined Pro Wrestling Guerrilla (PWG), a new promotion owned by SoCal wrestlers Super Dragon, Joey Ryan, Disco Machine, Topgun Talwar, Scott Lost and Excalibur. On October 18 he defeated Lost to become the last man to hold the APW-LA Light Heavyweight Championship and co-owned the Alternative Wrestling Show Tag Team Titles with Quicksilver. Later the APW-LA Lightweight title would become the AWS Light Heavyweight Title and Sky was named the first champion. Sky lost the Revolution Pro Junior title to Rising Son in December 2003 in a ladder match. His January 2004 rematch had to be postponed when doctors found he needed emergency surgery, which would sideline him for two months. He regained his title March 6, 2004 and remained champion for 10 months, surviving many title defenses.
In the Summer of 2004, Sky and Scott Lost toured for Osaka Pro Wrestling in Japan. On October 16 Scorpio Sky won the Revolution J Tournament, by defeating Super Dragon, Quicksilver and Joey Harder in a 4-way match. In November 2004 he debuted in Combat Zone Wrestling (CZW) in a "SoCal" match. AXP once again were named the Southern California Tag Team of the Year. In December 2004, Revolution Pro Wrestling held its final show where Sky lost the Revolution Pro Junior Heavyweight title to his partner Quicksilver.
In PWG, Sky and Quicksilver hooked back up with Dino Windwood as their manager to chase the PWG World Tag Team Championship. They received a shot at the champions Arrogance (Chris Bosh and Scott Lost), but were unable to dethrone them. On February 12, 2005 the Aerial Xpress was given a rematch for the PWG Tag Team Title but were once again defeated by Bosh and Lost. Later in June, The AXP defeated Los Luchas (Zokre and Phoenix Star), thus becoming #1 contenders for the PWG tag team title. Bosh and Lost forced through stipulations that if the AXP lost the match, not only would that be their last tag team title opportunity, but they would also be forced to remove their masks. The Masks vs. Title Match took place on July 9, 2005 at 2nd Annual PWG Bicentennial Birthday Extravaganza: Night One. Quicksilver was taken out of the match due to injury after Bosh hit him with a chair leaving Sky alone. Though outnumbered Sky was able to roll up Lost for a three count. The match would go on to be named the Southern California Match of the Year for 2005. Despite the victory Sky was assaulted after the match by Lost, Bosh, and "The Technical Wizard" Joey Ryan. The three bloodied Scorpio and removed his mask.
The next night Sky did not show up for a title defense and the Aerial Xpress were forced to vacate the title, and the team split. This led to Sky's "Disappearance To Africa" angle. Sky was seemingly out of the wrestling business, but finally made his return in September, without a mask, to attack Scott Lost after his match with Christopher Daniels at PWG's Battle of Los Angeles tournament. This led to a bitter feud between Sky and Lost ending with an "I Quit Match" in December, in which Sky was victorious.
Sky started 2006 on the sidelines with a knee injury. In February he returned and toured Germany and England on PWG's "European Vacation" shows. When they returned to the states Sky feuded with the Human Tornado. During this feud Sky broke Tornado's ankle in a match taking place in Las Vegas. Tornado's then manager Jade Chung turned on him and formed an alliance with Sky. The self-proclaimed "Scorpio Sky Experience" became hated by the fans quickly, and helped Sky climb to the top of PWG, defeating the likes of Kevin Steen, Chris Hero, Homicide and Human Tornado. Sky then went on to form a stable known as The Dynasty, consisting of himself, Jade Chung, Joey Ryan, Chris Bosh and Scott Lost.
It was at this time the rivalry between Sky and Frankie Kazarian began, after Sky assaulted Frankie after a match and cut his hair. In June, Sky toured in Europe, performing shows for 1PW, IPW, and Lucha Vavoom in England and the Netherlands. He competed in PWG's Battle of Los Angeles 2006 tournament on September 2, but was eliminated by Kazarian via disqualification after Jade Chung's interference. After Sky, Chris Bosh and Scott Lost defeated Kazarian and his tag team partners Chris Sabin and Alex Shelley, Frankie had enough and challenged Scorpio to a "Loser Leaves PWG" match which was to take place in January. On January 13, 2007 Scorpio Sky lost a "Loser Leaves PWG" match to Kazarian ending their nine month long feud and forcing Scorpio out of PWG.
While away from PWG Sky participated in MTV's Wrestling Society X (WSX). In WSX, Sky had the gimmick of being "the best athlete in history...of Montclair High" and carried around two plaques that were awards he had won. He competed against the likes of Matt Sydal, Jack Evans, and 6-Pac.
Soon after, The Dynasty seemingly brought Scorpio Sky back to PWG, but it was actually an impostor Sky who was noticeably smaller than the original. The real Sky would eventually come into the ring out of the crowd and beat the fake Scorpio Sky out of the building. In the summer of 2007, Sky and Joey Ryan feuded, ending with Sky defeating Joey Ryan and thus winning his reinstatement back into PWG. In October Sky made his official return to PWG teaming with The Young Bucks (Nick and Matt Jackson) to defeat Los Luchas (Zokre, Phoenix Star and Nemesis) in a 6-man tag. He then defeated Ronin at All Star Weekend 6 before teaming with him in a Round Robin Tournament defeating Los Luchas in the first round.
During the summer of 2011, Sky once again began regularly working for PWG, reforming the Dynasty with Joey Ryan. On August 20, Sky and Ryan defeated the RockNES Monsters (Johnny Goodtime and Johnny Yuma) to become the number one contenders to the PWG World Tag Team Championship. On September 10, Sky and Ryan failed to capture the PWG World Tag Team Championship from The Young Bucks.
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“We laugh at him who steps out of his room at the very moment when the sun steps out, and says: I will the sun to rise; and at him who cannot stop the wheel, and says: I will it to roll; and at him who is taken down in a wrestling match, and says: I lie here, but I will that I lie here! And yet, all laughter aside, do we ever do anything other than one of these three things when we use the expression, I will?”
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