He created multiple characters; perhaps the most notable being The Barbaric Berzerker (which functioned as a nickname attributed to Jimmy Jacobs), a tribute to The Berzerker (a wrestler who was famous for dressing and acting like a Viking warrior) and Bruiser Brody (an influential brawler). As The Barbaric Berzerker, Jacobs would wear large, furry boots, stomp on his opponents' hands, and constantly shout "Huss!". One of his earliest characters was Jumpin' Jimmy Jacobs, a gimmick which saw him hop to the ring on a pogo stick while wearing a top-hat. More recently he's also played the part of the Super Amazing Monkey (S.A.M. for short), a gorilla mascot for Fight Sport Midwest.
Jacobs, after the cage match against Whitmer, missing half of his front tooth. Jacobs and Whitmer continued to team as part of Lacey's Angels managed by Lacey. The team broke apart as Jimmy Jacobs was more concerned with winning Lacey's affections than winning matches. Jacobs would go on to make music videos for ROH professing his love for Lacey. After Jacobs and Whitmer split, the two began feuding in brutal matches. In one match at the Dragon Gate Challenge on March 30, 2006 Whitmer slipped on the top turnbuckle while attempting a super powerbomb that dropped Jacobs head and neck first on the ropes and edge of the ring. The two continued to wrestle several minutes longer. At In Your Face on June 17, 2006, Whitmer super powerbombed Jacobs into the crowd. Jacobs went on to injure Whitmer at Gut Check on August 26, 2006.
It was later revealed in a storyline that Lacey was sleeping with Colt Cabana. Lacey arranged for the two to be a tag team. Cabana left the team because he was annoyed at Lacey, and tried to explain to Jacobs that she was using him. Jacobs seemingly accepted Cabana's explanation, before assaulting him. BJ Whitmer made his way back from injury and continued his issue with Jacobs. When Brent Albright joined Lacey's Angels, their matches soon became tag-team, where Whitmer and Cabana would face Jacobs and Albright. Recently, it has progressed to the point where Daizee Haze has joined forces with Whitmer, and Lacey, in turn as the leader of the group, hired an "assassin", Mercedes Martinez. At The Chicago Spectacular: Night 2, Lacey was injured after Whitmer accidentally struck her in the face with a spike when Jacobs moved out of the way. Jacobs would go on to make his third music video (in which he has been described as being "demented") expressing his felling on her disfigurement.
On March 31, 2007 in his native town of Detroit, Michigan, Jacobs battled BJ Whitmer in what the Pro Wrestling Torch Newsletter called an instant classic. The two concluded their year long feud inside a steel cage. The bloodbath that ensued had the rabid ROH fans wanting more blood. Jacobs was able to prevail in this match, that had chairs, spikes, and barbed wire bats as weapons. Jacobs won with a Senton Backsplash off the top of the cage through a table. After the match it was announced that Jacobs lost a tooth and tore his ACL (an injury he previously had). He is expected to miss 6 - 9 months of action. Whitmer also suffered a neck injury in the battle.
While he was injured, ROH decided to continue the Lacey-Jacobs storyline with 4 small vignettes shown on YouTube, detailing a trip that Lacey spent in Chicago with Jacobs; afterward, he accompanied Lacey to the ring for her matches, in which they appeared to have swapped personalities.
For months leading into the ROH return to Chicago there were cryptic messages on a blog of a stable entering ROH that was code named "Project 161." Jimmy Jacobs was one of the names mentioned who could be behind this along with Adam Pearce and a few other Chicago based ROH wrestlers. At one point, posts related to Project 161 flooded the ROH Message Board, but ROH Booker Gabe Sapolsky has claimed these were actually fans doing it.
After making a successful return to ROH, Jimmy Jacobs, the returning Necro Butcher and the debuting Tyler Black violently attacked the Briscoe Brothers right after a brutal ladder match with Kevin Steen and El Generico. This meant Jimmy Jacobs was indeed behind Project 161. Jay Briscoe was hung upside from the rigging that was used to hoist the titles from the ladder match, as the blood of Jay Briscoe dripped onto Jimmy Jacobs he announced the beginning of The Age of the Fall. The angle was so controversial that ROH decided to remove the footage from the pay-per view that was being taped at the event. However, the footage was also heavily requested by ROH fans, so it was shown on the ROH Videowire for the week of September 15. Also, a "blood edit" of their debut is featured on the DVD of the event, Man Up. Later on in the event, Tyler Black and Jack Evans faced off in a dark match until both Jimmy Jacobs and Necro Butcher got involved. The Irish Airborne (David and Jake Crist) entered the ring to save Jack Evans, which lead to a six-man tag between The Age of the Fall and the make shift six-man team of Jack Evans and the Irish Airborne. The match battled to a no-contest as Necro Butcher punched out the referee during the middle of the match.
The day after their debut, their website revealed that all the blog entries had been written by Tyler Black. In an interview with a German website, Jacobs revealed there would be more people involved.
This was incorporated into British promotion 3CW in early November when Jacobs was revealed as the newest member of a similar faction in the promotion known as The Lost, managed by Sean David. Jacobs faced Sterling James Keenan on November 11th in a "Street Fight" in Middlesbrough, England.
A woman named Allison Wonderland would also become a follower of Jacobs on November 30, debuting in Dayton during a 4-Way Tag Team Scramble. At Unscripted III, Jimmy Jacobs gained arguably the greatest victory of his career, defeating former ROH World Champion Bryan Danielson with his new finisher, the End Time.
At Final Battle 2007, Jacobs and Tyler Black defeated the Briscoe Brothers to win the ROH World Tag Team Championship.
On January 25, 2008, Jacobs teamed with the returning Joey Matthews, the newest member of The Age of the Fall, in a losing effort against Roderick Strong and Rocky Romero of the No Remorse Corps. The following night, Jacobs and Black lost the ROH World Tag Team Championship to the No Remorse Corps' Davey Richards and Rocky Romero in an Ultimate Endurance match involving Brent Albright and BJ Whitmer of The Hangmen 3, and Austin Aries and Bryan Danielson.
On February 22, 2008, Jacobs introduced Zach Gowen as the newest member of the group. Following the announcement the two of them were defeated by the Vulture Squad of Jigsaw and Ruckus. The group at this time had an open invitation for Austin Aries to join them, writing blogs and posting YouTube videos about and directed at him. Tammy Sytch had made a counter offer to Aries of her services (including offering money and sex) against him joining the group. On March 30, 2008, Aries left the ring with Lacey, who was going to 'convince' him, and it was implyed that the two had sex. At this show Rain accompanied the group to the ring, as she has done in FIP, due to the fact the show was in Florida.
On April 19, Lacey left the group, siding with Austin Aries romantically. Aries also turned down the invitation into the group. Jacobs, heartbroken by Lacey leaving him, broke down in the ring to the chants of "Cry, Jimmy, Cry!" from fans and being covered with streamers. Later in the show Jacobs showed signs of a mental breakdown as he hit himself in the head with his trademark spike, to the concern of his fellow group members. The main event was changed as Jacobs pulled out. The Vulture Squad (Ruckus, Jigsaw and Jack Evans) were then beaten by the combination of Matthews, Black and Gowen (who replaced Jacobs). Post match Jacobs called out Aries and the two brawled, before Aries was jumped by Black, Matthews and Gowen. Jacobs went to attack Aries with his spike, but he stopped when Lacey begged him not to.