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Jeff Jarrett alliance & Women's Champion (1998-99)
In October of 1998, Devitt debuted on WWE television as Tori Poch, the valet and manager of Jeff Jarrett. At the beginning of her WWE career, Tori played the part of a businesswoman, wearing business suits. As the storyline went on, she also played the part of Jarrett's girlfriend.

In late 1998, Jarrett began a feud with Goldust that culminated in December at Rock Bottom: In Your House in a "Striptease match". During the match, Tori hit Goldust over the head with Jarrett's trademark guitar, enabling Jarrett to win. WWF Commissioner Shawn Michaels, however, disqualified Jarrett, and Tori had to strip due to the match's stipulations. As she stripped, The Blue Blazer and Jarrett covered her up. Tori, however, began utilizing a new strategy during matches, distracting Jarrett's opponents by unbuttoning her blouse. She would willingly take off her blouse to show the crowd her "puppies", a nickname originally bestowed upon her chest by wrestler Road Dogg and later utilized by commentator Jerry Lawler.

The strategy helped Jarrett and partner Hart defeat The Big Boss Man and Ken Shamrock to become World Tag Team Champions in January 1999. In February, Tori feuded with female professional wrestler Ivory, making her in-ring debut in a mixed tag match on Monday Night Raw. The same month, Jarrett and Hart retained the tag title in a tag match against Ivory's associates Mark Henry and D'Lo Brown at St. Valentine's Day Massacre with Tori's assistance. In March, the team lost their tag title to the team of Kane and X-Pac. She also competed in her first single's match, against Ivory but lost via disqualification after Jacqueline and Terri Runnels attacked Ivory during the match. As Tori continued to manage Jarrett and Hart, a potential storyline developed where Hart and Tori would have an affair, but the creative team vetoed the idea before it played out on-screen. A team name was also in the works — Tori favoring "Talent and Attitude" (T&A) — but Hart died in May 1999 at Over the Edge. Later in the event, Tori and Jarrett lost a mixed tag team match against Nicole Bass and Val Venis. Tori and Jarrett were interviewed moments after Hart's fall from the rafters at Kemper Arena, where Tori was noticeably shaken and fighting back tears of concern for her friend, and was unable to stay in her persona.

On May 2, 1999, Tori was scheduled to take on Sable in a 'Nightgown' match, but was made to compete against Nicole Bass, against whom she lost. On May 10, 1999, Tori won the Women's Championship from Sable in an Evening Gown match. Usually, in an Evening Gown match, the woman who forcibly removes her opponent's dress wins. Because Sable removed Tori's dress, she therefore should have been the winner. Commissioner Shawn Michaels, however, ruled that he considered the woman who had lost her dress the winner, crowning Tori the new Women's Champion. Tori lost the Women's Title to Ivory on June 14, due to interference from Nicole Bass.

At SummerSlam in 1999 Jarrett faced D'Lo Brown. During the match, Tori and Brown's former tag-team partner Mark Henry interfered on Jarrett's behalf, allowing him to win both the European Championship and the Intercontinental Championship. The following night, Jarrett awarded Henry the European title and gave Tori an assistant, Miss Kitty. Following an attack by Jarrett after losing a mixed tag match against Stephanie McMahon and Test, on September 26, Tori turned on Jarrett at Unforgiven and hit him over the head with a guitar in the middle of his match against Chyna for the Intercontinental Championship. Chyna pinned Jarrett, but referee Tom Prichard overturned the decision due to Tori's involvement. On the following episode of RAW, she participated in an inter-gender tag match with Chyna against the team of Jarrett and Prichard, in a winning effort.

Kane's girlfriend & DX (1999-00)
In November 1999, Tori returned as the much hyped girlfriend of Kane. On December 16, Tori complained to Triple H and Stephanie McMahon about Kane, by now feuding with his former tag team partner X-Pac, an ally of Triple H, being placed in a Handicap match. Stephanie retorted by challenging Tori to a match that night, which she accepted. Stephanie, however, replaced herself with X-Pac, who defeated Tori with ease as Kane was ambushed backstage by the Mean Street Posse. Kane received a shot at the WWF Championship on December 20 but with the stipulation that, if he lost to incumbent Big Show, Tori would have to spend the Christmas weekend with X-Pac. Kane lost after the New Age Outlaws distracted him. Tori insisted upon her return, however, that X-Pac had been a perfect gentleman. Around the same time, Tori began to become paranoid, and grew hysterical after Test hugged her. Kane promptly destroyed Test in the ring, believing Tori's claims that he had harassed her. Other wrestlers began to exploit Tori's neuroticism, using it to unleash Kane on their enemies. This included Mankind, who manipulated the duo into attacking a fake Mankind hired by Triple H and Chyna who manipulated Tori to get Kane to attack Chris Jericho.

Kane continued to feud with X-Pac, and on January 27, 2000 he was ambushed in the ring by the McMahon-Helmsley Faction when tricking him into joining DX X-Pac's allies. After tying Kane up, X-Pac revealed that Tori was now his girlfriend. Tori began accompanying X-Pac and his partner Road Dogg to the ring, becoming a member of the new D-Generation X in a brief heel turn. She helped X-Pac defeat Kane at No Way Out, but was unable to stop Kane from defeating him at WrestleMania 2000 and was also given a Stink Face from Rikishi during the match. Additionally, she helped Stephanie McMahon win the Women's Championship from Jacqueline in March At the King of the Ring in June, Tori, X-Pac, and Road Dogg participated in a table and dumpster match against the Dudley Boyz that ended with the Dudleyz powerbombing her through a table. During the match, Tori suffered a torn labrum which required surgery and took her away from television. On the October 30 edition of Raw, Tori returned in a segment at WWF New York, confronting and slapping X-Pac due to the events at King of the Ring.

Vince McMahon's Assistant and The Alliance (2001-02)
Tori began appearing regularly with Vince McMahon from February 2001, often in high profile segments. She also appeared in many segments with the McMahon family as a whole. The following month, she made a surprise appearance alongside Shane McMahon on the final broadcast of WCW Monday Nitro where he revealed that he had purchased WCW from under his father's nose. During the segment, the pair kissed and McMahon revealed that Tori was actually his wife and that she had helped McMahon sign the deal. Going forward, Tori was referred to as Tori McMahon.

At Wrestlemania X-Seven in April 2001, she accompanied Shane to the ring for his match against his father Vince, which he won following interference from Linda McMahon. She began to accompany Shane to the ring for his matches going forward, being at ringside for his match against The Big Show at Backlash and Kurt Angle at King Of The Ring 2001. McMahon became known as a co-owner of WCW and they began to lead their WCW wrestlers against his father and the WWF wrestlers, eventually turning heel by joining forces with Paul Heyman and his brand of Extreme Championship Wrestling (ECW) wrestlers, along with their new owner, McMahon's sister Stephanie McMahon-Helmsley. Calling themselves The Alliance, they pledged to finally run the WWF (and specifically their father) out of business. Ultimately, The Invasion came to a head at Survivor Series in a match to determine which power would ultimately have control. The team, each respectively representing The Alliance and the WWF, of McMahon, Stone Cold Steve Austin, Kurt Angle, Rob Van Dam, and Booker T lost to the team of The Rock, Chris Jericho, The Undertaker, Kane, and Big Show. The following night on Raw, the duo were thrown out of the arena. Later in the broadcast, Ric Flair revealed he was the new co-owner of the WWF and had hired Tori as his personal assistant. She appeared intermittently before being written off screen on June 10 when Vince McMahon defeated Flair for sole ownership of the company.

Feud with Kane and hiatus (2003-05)
At Wrestlemania XIX in March 2003, McMahon returned to WWE television during the Mr. McMahon vs Hulk Hogan Street Fight. Following the match, the couple came to the ring to check on Mr. McMahon's condition, being welcomed into the ring by Hogan. The couple turned face once more in the summer of 2003 by getting involved in a feud with Eric Bischoff, who had made improper remarks and gestures to Shane's mother Linda. He defeated Bischoff in a Street Fight at SummerSlam. McMahon also got involved in a bitter rivalry with Kane after Kane gave Linda a Tombstone Piledriver because she did not name him the number one contender to the World Heavyweight Championship. Their feud culminated in McMahon losing a Last Man Standing match at Unforgiven and to a first ever Ambulance match which he lost after a match at Survivor Series.

Raw GM, feud with DX and Bobby Lashley (2005-07)
On December 15, 2005, McMahon was named the new General Manager of Monday Night Raw after Eric Bischoff was fired. She only appeared sporadically as she was heavily pregnant with her second child. At the 2006 Royal Rumble, McMahon distracted Shawn Michaels allowing Shane to eliminate him by throwing him over the top rope. After weeks of attacks from behind by Shane, one of which saw him force an unconscious Michaels to kiss Vince's rear end, Shane and Michaels faced each other in a Street Fight on the March 18, 2006 Saturday Night's Main Event XXXII. In a fashion similar to the real life Montreal Screwjob, Shane put Michaels in the Sharpshooter as Vince called for the bell and gave Shane the victory. A week later, McMahon gave birth to her second son.

A week after giving birth, McMahon appeared at Wrestlemania 22, managing Vince McMahon in a losing effort against Michaels. The McMahons' feud with Michaels took a religious turn after WrestleMania 22. Vince claimed that Michaels's victory was a result of "divine intervention" and booked himself and his son in a match at Backlash against Michaels and his tag team partner "God". Around this time, Vince began to act strangely and at one point considered himself a god. Shane, who at this time was referred by Vince as "the product of his semen", teamed with Vince to defeat Michaels and "God" at Backlash, due to help from the Spirit Squad.

This feud later enveloped Triple H, who the McMahons had enlisted to take out Michaels. Triple H was getting frustrated with this, as it was distracting from his quest to regain the WWE Championship. Triple H wound up bashing Shane with his signature weapon, the sledgehammer, in what was considered to be an accident that put Shane out of the ring for a while. Vince (and later Shane, who had recovered) sought to humble Triple H and get some retribution. Triple H then began a feud with the McMahons shortly after, leading to his siding with Shawn Michaels and the reformation of DX. At SummerSlam, the McMahons were defeated by DX. About a month later at Unforgiven, The McMahons and then ECW World Champion Big Show faced DX in a Hell in a Cell match. Shane was injured after Michaels elbow dropped a chair which was around Shane's neck. DX emerged victorious at Unforgiven, and Tori and Shane disappeared from television. She would return in March 2007 and continued to manage The McMahons until September 3, 2007 when she was again written off television.

Randy Orton relationship and Evolution (2002-05)
On April 25, 2002, Tori returned to the now-renamed WWE by introducing her new client, the debuting Randy Orton, who won his match against Hardcore Holly. Soon after, Tori and Orton became fan favorites and were placed in a series of matches with Holly. In September 2002, the pair were drafted to the Raw brand, where Orton defeated Stevie Richards in his debut on the show. Within weeks of their debut on Raw, Orton suffered a shoulder injury which left him sidelined for months. While recovering, Tori and Orton still appeared on Raw in their own Randy News Network (RNN) segment, a weekly vignette featuring him talking about Orton's condition. The show interrupted other segments of Raw programming, which caused Orton to slowly transition himself into a narcissistic and self-centered villain.

After his injury healed, Tori and Orton joined the Evolution stable, which consisted of Ric Flair, Triple H and relative newcomer, Batista. The group was pushed on Raw from 2003 to 2004, with the height of their dominance occurring after Armageddon in 2003 when all of the men's titles on Raw were held by the members of Evolution with Tori winning her third Women's Championship at the event. In 2003, Tori and Orton spent much of their time helping Triple H overcome challenges for the World Heavyweight Championship. Afterwards, Orton proclaimed himself "The Legend Killer", a young upstart who was so talented that he touted himself as the future of professional wrestling. He embarked on numerous storyline feuds with "legendary" wrestlers and gained infamy for his blatant disrespect of many older, well-respected names in wrestling history. With the help of his stablemate and mentor Ric Flair, he defeated Shawn Michaels at Unforgiven in the first of many high-profile matches billed as "Legend versus Legend Killer." During this time, Orton began using the move that would become his signature finisher, the RKO, a jumping cutter named after his initials.

At Summerslam, Orton defeated Christ Benoit for the WWE World Heavyweight Championship, thus becoming the youngest world champion in WWE history at the age of 24. The following night on Raw, after Orton successfully defended the title against Benoit in a rematch, Evolution threw Orton a mock celebration only to reveal that they were not pleased with his new victory. While Batista had Orton propped on his shoulders in elation, Triple H gave him a pleased thumbs-up and then abruptly changed it to a thumbs-down, which was followed by Batista dropping Orton to the mat. Tori also received a Batista Bomb and a Pedigree from Triple H, resulting in the pair being kicked out of Evolution. The move turned Orton and Tori into fan favorites in the resulting feud with Evolution. A month later, Orton lost his championship to Triple H at Unforgiven after interference from Flair, Batista, and Jonathan Coachman. In January 2005 at New Year's Revolution, Orton participated in an Elimination Chamber match for the vacant World Heavyweight Championship, where he was the last man eliminated by Triple H after interference from Ric Flair and Batista. On the January 10 episode of Raw, Orton defeated Batista to earn a match against Triple H at the Royal Rumble for the World Heavyweight title, which he lost.

On March 21, 2005, Orton attacked Tori, knocking her unconscious with an RKO. Orton explained his actions as showing The Undertaker that he would be willing to do anything to end his Wrestlemania streak. The attack saw an end to Tori and Orton's relationship on-screen.

Return to DX and Rated-RKO (2006-07)
Following a near 20 month hiatus, Tori returned to WWE at the Cyber Sunday event. During a match between DX and Rated-RKO, special guest referee Eric Bischoff allowed Randy Orton and Edge to use illegal tactics leading Tori to enter the arena and slap Bischoff. She also faced up to Orton and was speared by Edge, giving DX their first loss since reuniting in June 2006. Tori began managing Triple H and Shawn Michaels through their feud with Rated-RKO, including their win at Survivor Series.

At New Year's Revolution in January 2007, Tori turned on DX to reunite with off-screen boyfriend Randy Orton and Edge, becoming their manager until their eventual split in May.