Jimmy Olsen debuted alongside Colin Olsen as the Olsen Twins at the late 2006 tag team tournament to decide new Campeonatos challengers, but the two lost in the opening round to Cheech and Cloudy. This performance would earn them a regular spot on the CHIKARA roster.
The Olsens returned for a baptism of fire at King of Trios, as Colin and Jimmy were brutalized at the hands of Yoshiaki Yago and MIYAWAKI. They achieved their first CHIKARA win during a gauntlet match on night 3 of that weekend by beating 2.0 in 4 seconds during a Tag Team Gauntlet. Unfortunately, this would prove to be one of their only wins, with another coming at Young Lions Cup when they upset the North Star Express. They would begin teaming occasionally teaming with NWA Upstate colleague Brodie Lee in trios matches, often tackling The Colony, and their adventures in tag team wrestling saw even more enthralling contests with Cheech and Cloudy, including a widely praised match at the “Cibernetico & Robin” event.
Colin's signing with the WWE in early 2008 forced Jimmy into full-time singles wrestling, which he proved to be rather good at, defeating the likes of Icarus and Player Uno while taking Vin Gerard and Gran Akuma to the limit. However, a first round loss to Stupefied in the Young Lions Cup - and Vin Gerard revealing where Colin had really gone - caused Jimmy to turn against the fans who had grown to love him as he began to unmask several wrestlers, seemingly hunting for Colin. However, when Colin returned in September, Jimmy declared his hunt for Colin to be over, and thus ending his grudge against any masked wrestlers. This did not end well though as Colin determined that Jimmy had become weak, and as a result Colin turned on his brother and joined the UnStable. Now firmly back in the tecnico camp, Jimmy looks to gain adequate revenge on the rudos who tricked him and betrayed him. He formed a successful tag team with former foe Lince Dorado, and has recently donned the old Equinox attire in an effective attempt to get into the head of Vin Gerard.
The year began with the formal announcement of Lince, Jimmy and Helios as a full-time unit in CHIKARA, dubbed The Future Is Now. Things got even better for Olsen when he finally vanquished Vin Gerard, this time in a ladder match, to become the new CHIKARA Young Lions Cup Champion.
- Finishing and signature moves
- Jumping Piledriver
- Straight Right Hand
- Running corner crossbody
- Tope into a tornado DDT
- Missile Dropkick
- Tag teams and stables