The history of the Italian Connection is an interesting, yet sad, one to cover. T2P had fully established themselves by their 3rd Japan landing, after their Strength Assessment league. Milano Collection A.T. had dominated, defeating everyone with ease. Masato Yoshino and Stevie "brother" Tsujimoto were the closest to him in rank, and part of the "Heel Big 3" of T2P. Other than this, however, the lines weren't clearly drawn as to who was aligned with who, or face or heel. Milano changed this on 3/3/2002. He had defeated Yoshino in the finals of the T2P league in convincing fashion. He announced the formation of the first formal unit, and he was naming it the "Italian Connection". He invited his friends Tsujimoto and Yoshino, along with the up and coming Takayuki Yagi and Shuji Kondo. He gave Italian names to them. Yoshino became YOSSINO, Kondo became Condotti Shuji after a famous shopping district, Yagi became Pescatore Yagi since he was a Fisherman at the time, and Tsujimoto became YASSINI. He wasn't too happy with this, so after some arguing he became "brother" YASSINI. The group returned to Mexico and were not active until May. At the Toryumon Mexico performance they debuted, all members sporting Italian colour ring costumes. Berlinetta Boxer joined the group, which was a natural fit since he was an Italian made car. They began a feud with Crazy MAX (which had really begun on 3/3 when Fujii kidnapped Milanos' invisible dog Mikeru.) which would be the spearhead of Toryumon Japan vs. T2P. T2P returned to Japan in June, and the ItaCon dominated the ring. Milano met Fujii on the T2P tour finale in Korakuen on 6/6 to get Mikeru back (Fujii tried to bring Milano a real dog, but he saw through the ruse....no pun intended...). The ItaCon and CMAX had a huge brawl afterwards, and Fujii stole Mikeru back yet again, despite losing the match. This was the first T2P vs. Japan conflict to happen in Japan (aside from Milano killing Ryo repeatedly), and triggered the Summer 2002 feud regarded by many as the best period in Toryumon history. Shuji, Boxer, and Yagi stayed in Toryumon Japan, representing the Italian Connection in the Japan ring. They were very successful, including a big win in the opener of the 2002 World show. Milano appeared after that match, again provoking Toryumon Japan wrestlers.

9/8/2002 is a major turning point date for Toryumon, and is the start of the next chapter of the Italian Connection. Ariake Coliseum was the location for the Toryumon Japan vs. T2P show, which featured matches around that concept. Milano, YOSSINO, and YASSINI defeated Crazy MAX for the UWA 6 Man tag belts, Milano submitting CIMA within the confines of the T2P 6-sided ring. The crowd reaction to this wasn't great at the time, but as Summer turned to Fall, this became the hottest feud since the early days of CMAX vs. M2K. CMAX finally got the better of the ItaCon on 10/28 in Korakuen Hall, when SUWA (who had been busy feuding with Touru Owashi) made his entrance into the feud and pinned Yagi in an 8 man tag. CMAX would strike another blow 1 month later, when they recaptured the UWA trio belts, SUWA pinning YASSINI. This all built towards CIMA vs. Milano on the final Korakuen show of the year, and final of a series of 3 Korakuen shows that showcased T2P, Japan, and the returning Ultimo Dragon. Fujii kidnapped YOSSINOs' pet gorilla Venezia on the first of the 3 shows, imprisoning the animal in Ueno Zoo. CIMA gave Milano his first direct defeat since his debut match, and due to the match stipulations, forced the dismissal of T2P. Milano, YOSSINO, and Shuji tried in vain to stop this by facing Anthony W. Mori, Henry III Sugawara, and Taiji Ishimori in Ishimoris' Japan unveiling at WRESTLE-1 in the Tokyo Dome. Ishimori pinned Shuji, keeping the T2P dismissal intact. The entire Italian Connection stood in the ring on 1/23/2003 on a Toryumon Japan show, and declared they were indeed Japanese, not Italian. Shuji finally admitted he hated fashion and shopping, while Yagi revealed he was not the son of a fisherman, but of a baker! Milano banished Yagi to the bakery, to learn his family trade. Boxer didn't say anything, but YASSINI implied that he may have been manufactured in a Japanese factory.

2003 brought the beginning of very troubled times. The popularity of Milano and YOSSINO caused an increasingly large divide, as Shuji, Boxer, and YASSINI remained true to the heel origins of the group. Milano and YOSSINO would insist on keeping matches clean, but the others continued to interfere into matches heavily. Shujis' interference even cost Milano his El Numero Uno quarterfinal match with Mochi, eliminating him from the tournament. It began to boil over when YASSINI was injured in early summer. He spent a lot of his rehab time on the internet, and made a large amount of often bizarre posts on the ItaCon blog. Milano began scolding him on the blog, eventually YOSSINO joining in. This eventually carried over to the ring with increasing miscommunication and dissention. Yagi returned with a new baker persona (becoming Bakery Yagi), but was clearly on the heel end. Relations deteriorated until they came to a head on 8/30/2003, when Shuji and YASSINI attacked Venezia and removed his mask. YOSSINO came to his aid which lead to a a pull apart. Milano tried to keep the peace, but was attacked. The ItaCon had officially exploded. Yagi and Boxer would also leave, all of the departures going on to form Aagan Iisou (or in Yagis' case, become a referee and an American masked man). Milano and YOSSINO continued on, aligning with Anthony W. Mori who saw his Royal Brothers group meet a similar fate. Mori didn't officially join out of hope the Royals would get back together, but gave the group enough manpower to stay alive through the end of 2003. Milano chose to team with Magnum TOKYO for Rey de Parejas 2003, while Mori and YOSSINO stayed together. They didn't fair very well, as Mori continued to struggle.

2004 wasn't much better. Anthony re-aligned with Henry III Sugawara who returned from Toryumon X to reform the Royal Brothers. Milano and YOSSINO made a shaky alliance with Do FIXER, who were also low on manpower. Sugawara betrayed Mori and joined Aagan Iisou. Mori officially gave up his Royal Brothers dream, and joined the ItaCon as an Italian Prince. Mori still could not find steady success, and Milano became saddled by injuries. YOSSINO finally defeated Milano in the ItaCon decision match for the UDG Belt tournament, which spoke volumes about the changing times.

Rey de Parejas 2004 was going to be important for the ItaCon. Milano told Mori he needed to step his game up for the ItaCon to survive. They defeated the Magnum lead Do FIXER in their first match, Milano unveiling his IR finisher. They went on to win the tournament, and became the first Open the Triangle Gate champions. The next tour was named ITALIAN REVOLUTION, and showcased the resurgent Italian Connection. They rolled through the end of the year, and went into 2005 with a huge winning streak and great hope.

The first show of 2005 saw them successfully defend the Triangle Gate, but then a huge slump began. Rumours began circulating about Milano and him being unhappy with the direction of the company since becoming Dragon Gate. With the Aagan Iisou dismissal still a freshly stinging wound, fans held out hope that it would prove to be false. The ItaCon began losing on every show, with a big Triangle Gate defense coming up. Milano abruptly announced he was taking time off due to injury (his leg had a bad muscle tear that had been bothering him for close to a year). The Triangle Gate was vacated, Anthony went off with Magnum, and YOSSINO began focusing completely on the rapidly approaching Open the Brave Gate tournament. YOSSINO reformed his alliance with K-ness after the tournament, but not joining Final M2K. 3/27/2005 brought the final fatal blow, as Anthony formally announced the formation of the Do FIXER splinter group Pos.HEARTS, while YOSSINO betrayed K-ness and joined Blood Generation as Masato Yoshino.

After the events of 3/27, Milano announced he would be leaving to do some soul searching in the US, and wherever else his travels take him. He said the ItaCon was not being dissolved, but as the only member, the group left Dragon Gate with him. The departure of the Italian Connection signals the end of the last symbol of the T2P generation. While their direct impact has decreased steadily since they were initially conceived, there is no denying their importance in Toryumon/Dragon Gate history.