On May 19,2003, Triple H chose his manager Ric Flair to face for the World Heavyweight Championship, thinking that Flair would lay down for him. Shawn Michaels told Ric Flair that 15 years ago, Flair would come on TV and tell everyone that he was the man and he was the measuring stick. He was what every wrestler should aspire to be. Ric asked Shawn "Do you still think I can beat a guy like Triple H?" Shawn answered "I know you can do it. "Ric Flair almost beat HHH for the Heavyweight Title that night.
The next week on Raw, Shawn came to the ring to talk to Ric. He said "After what I saw you do to HHH, you were, are and will always be, in the heart of Shawn Michaels, the greatest wrestler in the world." Shawn then told him he wanted to know if he was in the same league as Ric Flair and the match was on. In a handicap match, Flair and Michaels vs HHH, Flair attacked Shawn. He attacked Shawn because although he was flattered that Shawn said he was the greatest, he thought that Shawn will always be a Ric Flair wannabe. Shawn came out and said he's not a little boy watching his idol Ric Flair on TV, he's a man who has established the names "The Heartbreak Kid","The Showstopper", "The Headliner", "The Main Event." He also said that Flair didn't pass the torch to him, Shawn took it from him.
Ric Flair entered the ring first wearing a gold robe with diamonds in it. Shawn, wearing the colors of the Texan flag, entered next to a huge pop being the hometown hero. The match begins with an HBK chant. Flair struts around the ring. They tie up, Flair puts on a headlock and a wristlock before pushing HBK. Flair struts around, then yells "Woooo!"They tie up again, Shawn uses a headlock, a wristlock and a single leg takedown before doing Flair's signature strut on his back. HBK knocks down Flair with a brutal slap before yelling out "Woooo!" They tie up again, Flair uses a go behind waistlock, takes down HBK, Shawn reverses into a waistlock but Flair struggles to the ropes to force a break. HBK pushes Flair into the ropes and slaps him. Shawn drop toe holds Ric and goes into a front headlock but Flair pushes Shawn into the ropes. Shawn does the same. HBK knocks down Flair with a right hand and clotheslines him over the top rope to the floor. Shawn hits a huge crossbody over the top rope. Flair goes in and begs for mercy before kicking Shawn in the gut. Flair chops Shawn, Shawn punches Ric and shoulder blocks him down. HBK runs off the ropes, Flair turnsover and HBK applies a side headlock. Flair puts Shawn in the corner and drives the forearm into the stomach before chopping his chest. Shawn hits his own chops on Flair. He climbs the 2nd rope and punches Ric. Ric tries a Manhattan Drop but Shawn gets out and knocks down Ric. Shawn continues punching Flair until the ref forces Shawn to break. With Shawn arguing with the ref, Ric charges and clips Shawns left knee. Flair kicks the knee, then delivers a rolling kneedrop into the knee. HBK tries getting up but he can't. In the corner, Flair chops Shawn and kicks his knee. Slick Ric yanks on the injured left leg and drives his knee into the back of HBK's leg. He places Shawn's leg on the first rope and jumped on it. The Nature Boy finally puts on the Figure 4 Leglock. Shawn is screaming in pain and tries to untangle himself but he can't. Shawn's shoulders hit the mat for 2. Shawn reaches for the ropes he's too far away. Ric gets another 2 count off the Figure 4. Shawn finally turns over and grabs the ropes. Ric knocks down Michaels with a chop and stomps at the knee. He grabs the leg while Shawn is standing but gets an enziguri. Both men get up and exchange chops and punches. HBK uses a backdrop and Irish Whips him into the corner. He charges but Flair back elbows him down. Flair goes to the top but is slammed off. Shawn goes for the Superkick but gets caught and the Nature Boy immediately goes for the Figure 4 but falls victim to a Small Package for a close 2. Michaels goes for a Figure 4 on Flair but Flair pokes him in the eye. Flair tries a back suplex but Michaels flips out and hits a Rolling Clutch Pin for 2. Flair grabbed the tights to put Shawn in his own Rolling Clutch for 2. They exchange chops and Flair is whipped into the corner. Ric does the Flair Flip and goes to the top rope but is clotheslined down. HBK hits a superplex on Flair. Shawn goes outside and sets up a table. Back in, Flair tries to suplex Shawn over the top through the table but gets sent into the stairs and set up on the table. Suddenly, Randy Orton runs towards Shawn from the crowd but gets the Superkick. Shawn climbs to the top rope and leaped off changing direction in midair to deliver a splash through the table. Shawn cut his arm and Flair is bleeding from the back of the head and back.Back in the ring, Shawn gets a 2. They get up in the corner where Flair mule kicks HBK and the ref. The Nature boy limps over to Shawn who chops him down and backdrops him. Flair whips Michaels off the ropes but gets a flying forearm. Shawn kips up and scoop slams Flair. He goes up top and delivers an elbowdrop. Shawn goes to the corner and warms up the band before hitting Naitch with some Sweet Chin Music. He turned around right into a chair to the face by Randy Orton. Orton drags Flair on top of Shawn Michaels and Earl Hebner counted the 3 at 14:17. After the match, the referees helped Shawn and Earl Hebner as Randy Orton helped Flair to the back.