Jake The Snake Roberts vs. The Million Dollar Man Ted DiBiase (Mar 1989 – Apr 1990)

Background

Ted DiBiase came into 1989 having already failed, twice, to get his hands on a legitimate world title. He lost the WrestleMania IV tournament final to Randy Savage in 1988, then spent that summer teaming with André the Giant as "The Mega Bucks" against Savage and Hulk Hogan's Mega Powers at the first SummerSlam, a match his team lost.[1] Before that, DiBiase had arranged to buy the WWF Championship outright from André after André beat Hogan under contested circumstances in February 1988, only for WWF President Jack Tunney to rule the title vacant rather than recognize a purchased championship.[1]

With the door to a real title shut, DiBiase had his own belt made. Pat Patterson is credited with suggesting that if DiBiase couldn't win a championship, he should simply commission one, and DiBiase had Betteridge Jewelers of Greenwich, Connecticut build a gold-and-silver belt studded with roughly 700 cubic zirconia stones, valued at the time at around $40,000.[3][4] Vignettes of DiBiase overseeing the belt's construction ran on WWF television for weeks before he unveiled it on The Brother Love Show on March 4, 1989, calling it the Million Dollar Championship, a title the WWF itself never sanctioned.[3][4] DiBiase later called it one of the best business decisions of his career: "Everybody wants to take a picture with the Million Dollar Belt and me. The Million Dollar Belt made me more money than the WWF Title ever would have."[5]

Jake Roberts, meanwhile, was still working through the physical toll of his 1987 program with The Honky Tonk Man, in which a guitar shot to the back during a *Snake Pit* segment left him picking wood splinters out of his skin for weeks and drew focus to real problems with the discs in his back.[2] He'd also spent much of 1988 in a personal, uncomfortable program with Rick Rude and Bobby Heenan, after Rude pulled Roberts' real wife Cheryl from the crowd and later wore tights bearing her image.[2] By early 1989, Roberts wasn't chasing the Intercontinental or WWF titles either; DiBiase's homemade championship, and the money-and-morality story built around it, became his assignment instead.[1][2]

Build-up

Roberts and DiBiase had worked together going back to Mid-South Wrestling, and it showed in an early skirmish on MSG Network on April 24, 1989: roughly fifteen minutes of Roberts controlling with Damien always in the corner, DiBiase stalling and bailing to avoid the snake, and Virgil grabbing Roberts' leg on a DDT attempt before Roberts won by rollup anyway.[7] DiBiase and Virgil jumped Roberts after the bell, and the segment ended with Roberts running them off by brandishing Damien's bag, a visual the feud would return to all year.[7]

The angle turned serious on the May 6, 1989 *Superstars*. DiBiase, out that week with the flu, sent Virgil in against Roberts instead; Roberts beat Virgil with the DDT, and DiBiase attacked him at ringside afterward, finishing him off with his own Million Dollar Dream sleeper.[6] The WWF sold the beating as a legitimate neck injury, and on the June 24 *Brother Love Show*, DiBiase told Brother Love that Roberts was in the hospital having a disc removed from his neck.[6] Roberts stayed off WWF television for months; at SummerSlam on August 28, DiBiase and Virgil beat Jimmy Snuka by count-out with no Roberts program to speak of, marking time until the real feud could resume.[1]

Roberts came back on the October 7 *Superstars*, pinning enhancement wrestler Brian Costello with the DDT, and the DiBiase matches picked back up on the house-show and television circuit through the rest of 1989.[6] A December 14 bout in Hamilton, Ontario ran the same pattern as their earlier matches: methodical DiBiase control, Roberts chasing the DDT, Virgil finally costing Roberts the finish with an ambush from behind for a disqualification, then a post-match beatdown that ended with Roberts DDTing Virgil in front of Damien's bag.[8]

The angle that defined the program aired on the January 20, 1990 *Superstars*. After DiBiase squashed jobber Lee Park and held the belt up, calling it the most expensive title in wrestling, Roberts stormed the ring, clotheslined DiBiase over the top rope, and zipped the Million Dollar Championship into the bag holding Damien.[9][10] Jesse Ventura objected on commentary, calling Roberts a thief as the crowd cheered him for it, and neither DiBiase nor Virgil would reach into the bag to get the belt back.[10] The following night at the Royal Rumble in Orlando, DiBiase entered at number one and Roberts at number four; Roberts went for a DDT on DiBiase before Randy Savage eliminated him, a passing skirmish rather than a resolution.[25]

The bag standoff played out across several more weeks of television. On the January 27 *Superstars*, DiBiase ordered Virgil into the ring to get the belt, slapping him and waving money at him when he balked; Virgil finally reached in, panicked, and ran to the back with DiBiase chasing after him, both of them now visibly afraid of Damien.[11] DiBiase's solution was to hire outside muscle: he paid manager Slick to send Big Boss Man after the bag. Boss Man got it on the February 24 *Brother Love Show*, then, instead of collecting DiBiase's money, told both Slick and DiBiase he couldn't be bought, returned the bag and the belt to Roberts, and walked off to a babyface ovation, in one of the WWF's more memorable face turns of the year.[4][12]

The Matches

Roberts and DiBiase settled the year-long program at WrestleMania VI, on April 1, 1990, before an announced 67,678 at Toronto's SkyDome, a building-record crowd for that venue at the time.[15] The Million Dollar Championship, still unrecognized by the WWF itself, was on the line for the first time in a match that mattered to the story rather than a house-show tune-up.[17]

The match ran close to twelve minutes and struggled for stretches to hold the SkyDome's attention; cameras caught a sizable chunk of the crowd doing the wave through the middle portion, one of the only times a "wave" has been visible mid-match at a WrestleMania.[18] DiBiase and Roberts used the lull rather than fighting it, working the closing stretch to pull the crowd back before the finish.[18] Dave Meltzer's Wrestling Observer Newsletter rated the match 2.5 stars, in the middle of the SkyDome card.[16]

The finish came at 11:50: Virgil pulled Roberts off the ring apron and away from the referee's count, and DiBiase was awarded the match by count-out, keeping his self-made title without ever needing to beat Roberts clean.[17] Roberts wasn't finished making his point. After the bell he ran off Virgil, DDT'd DiBiase, and grabbed a wad of DiBiase's own money, throwing bills out to ringside fans, among them, by some retrospective accounts, actress Mary Tyler Moore.[18]

Aftermath

DiBiase kept the Million Dollar Championship, and kept it exactly the unofficial, self-awarded prize it had always been; the WWF never folded it into a sanctioned title picture. He spent the rest of 1990 as a mid-card fixture with Virgil at his side, and the two stayed paired into 1991, when Virgil's own resentment at being bought and ordered around finally boiled over into a rebellion, DiBiase's next program built on the same "everybody's got a price" premise turned back on its own manager.[13][14]

Roberts moved on from DiBiase into a program with Bad News Brown that summer, before Rick Martel sprayed his own cologne, Arrogance, into Roberts' eyes that fall, blinding him in storyline and setting up the WrestleMania VII blindfold match.[2] Big Boss Man's face turn stuck; he beat his old tag partner Akeem in under two minutes on the same WrestleMania VI card, the first live payoff of the refusal-to-be-bought story that had made him a fan favorite five weeks earlier.[12]

Behind the Scenes

The injury that took Roberts off television in mid-1989 wasn't quite what fans were told. DiBiase's ringside attack and Million Dollar Dream on the May 6 *Superstars* was presented as the cause of a herniated neck disc, but at least one detailed timeline of the angle notes that the real reason for Roberts' absence was legal trouble rather than a wrestling injury.[6] Roberts had been arrested in May 1989 and charged with aggravated battery over punching a man during a night out at a Daytona Beach strip club the previous December; he was convicted that July, sentenced to ten years' probation, and only had the conviction overturned later on appeal after a court found his defense had been inadequate.[22][23] The kayfabe neck surgery gave the promotion a clean, sympathetic cover story for a wrestler who was actually dealing with a criminal case.

DiBiase's own life carried an irony the character never let on. The Million Dollar Man's whole gimmick was showing off wealth other people couldn't touch, flashing cash, humiliating fans and enhancement talent for a hundred-dollar bill, needling Roberts specifically about who could be bought and who couldn't.[5] Off camera, by DiBiase's own later account, this exact period of his career was when infidelity and the pressures of the road put real strain on his marriage to his wife Melanie, a rupture that didn't come to a head and get repaired until a Christian conversion in 1992.[24] The performer selling "everybody's got a price" was, by his own admission, privately failing to live up to the price of his own family life.

The two men's public accounts of the WrestleMania VI match itself don't line up. On his *Everybody's Got a Pod* podcast, DiBiase said flatly of the match, "I'll say it for you, we stole the damn show."[19] Roberts, on his own *The Snake Pit* podcast, pushed back on that framing: "It was never my idea to try to steal the show. In fact, it would be the furthest thing from my mind."[20] Both men agree the match ran long and worked, in DiBiase's word, "great" for a mid-card program with no sanctioned title on the line; they simply credit the outcome to different intentions.[19][20]

The Boss Man face turn that grew out of this feud wasn't originally built as a springboard to a new headline run. It was a character beat, a bodyguard refusing to be bought, that happened to land well enough with the SkyDome crowd that the WWF kept him as a fan favorite afterward, pairing him against his old partner Akeem later that same night.[12] Cagematch's promo database preserves one of Roberts' pre-match interviews building to WrestleMania VI, in which he turned DiBiase's own money-flaunting back on him: reminding DiBiase of the people he'd made grovel and beg for cash over the years, Roberts promised, "this time you'll be the one that grovels for the money."[21]

Legacy

The Million Dollar Championship never became a sanctioned WWF title and was never defended as one after this program; it stayed a prop of DiBiase's character, changing hands only a handful of times over the rest of his run, including the 1991 rebellion when Virgil beat him for it at SummerSlam before DiBiase took it back with Repo Man's help that November.[13][14] Roberts and DiBiase never had a rematch specifically over the belt; the story ended, appropriately for a title nobody official ever recognized, on a count-out.[17]

At the time, Dave Meltzer's Wrestling Observer rated the WrestleMania VI blow-off 2.5 stars, a respectable but unspectacular number for a card headlined by Hulk Hogan and Ultimate Warrior's title-for-title main event.[16] Retrospective reviewers have singled out the crowd doing the wave through the match's slower stretches as one of the stranger visual footnotes of any WrestleMania, alongside Roberts throwing DiBiase's own money into the crowd afterward as a coda that outlasted the match itself in fan memory.[18]

Big Boss Man's face turn out of this program became the more durable legacy piece. What began as a one-off refusal to take DiBiase's money turned into a permanent character shift, and Boss Man spent the rest of his WWF run as a lawman babyface rather than the corrupt guard gimmick he'd carried into 1990.[12] DiBiase, for his part, kept the Million Dollar Man character running for years afterward, later crediting the specific decision to build his own title, rather than keep chasing a real one, as one of the more lucrative choices of his career.[5]

See Also

Sources & Further Listening

1. Ted DiBiase — Wikipedia. https://en.wikipedia.org/wiki/Ted_DiBiase
2. Jake Roberts — Wikipedia. https://en.wikipedia.org/wiki/Jake_Roberts
3. "The true history of WWE's most expensive title: the Million Dollar Championship" — Ted DiBiase's official site. https://milliondollarman.com/the-true-history-of-wwes-most-expensive-title-the-million-dollar-championship/
4. "The History Of The Million Dollar Championship" — The Signature Spot. https://www.thesignaturespot.com/articles/the-history-of-the-million-dollar-championship
5. "Ted DiBiase - The Art of Being a Million Dollar Heel" — Pro Wrestling Stories. https://prowrestlingstories.com/pro-wrestling-stories/ted-dibiase/
6. WWF Superstars 1989 episode-by-episode results — The History of WWE. https://thehistoryofwwe.com/wwf-superstars-1989/
7. "Jake Roberts vs Ted DiBiase (WWF, 4-24-1989)" — Tape Machines Are Rolling. https://tapemachinesarerolling.wordpress.com/2018/11/05/jake-roberts-vs-ted-dibiase-wwf-4-24-1989/
8. "Jake Roberts vs Ted DiBiase (WWF, 12-14-1989)" — Tape Machines Are Rolling. https://tapemachinesarerolling.wordpress.com/2020/05/25/jake-roberts-vs-ted-dibiase-wwf-12-14-1989/
9. "Jake Roberts steals the Million Dollar Championship: Superstars, Jan. 20, 1990" — WWE.com. https://www.wwe.com/videos/jake-roberts-steals-the-million-dollar-championship-superstars-jan-20-1990
10. WWF Superstars of Wrestling, January 20th, 1990 recap — Scott's Blog of Doom. https://www.blogofdoom.com/2017/06/09/wwf-superstars-of-wrestling-january-20th-1990/
11. WWF Superstars of Wrestling, January 27th, 1990 recap — Scott's Blog of Doom. https://www.blogofdoom.com/2017/06/13/wwf-superstars-of-wrestling-january-27th-1990/
12. Big Boss Man — Wikipedia. https://en.wikipedia.org/wiki/Big_Boss_Man
13. Million Dollar Championship — Wikipedia. https://en.wikipedia.org/wiki/Million_Dollar_Championship
14. "Abandoned: The History of the Million-Dollar Wrestling Championship" — Bleacher Report. https://bleacherreport.com/articles/997220-abandoned-the-history-of-the-million-dollar-championship
15. WrestleMania VI — Wikipedia. https://en.wikipedia.org/wiki/WrestleMania_VI
16. Dave Meltzer star ratings for WrestleMania VI — IWNerd. https://www.iwnerd.com/dave-meltzer-star-ratings-wrestlemania-6-vi/
17. "The Backstory Behind All Matches At Wrestlemania 6" — The Sporting Tribune. https://www.thesportingtribune.com/2026/02/18/backstory-behind-all-matches-at-wrestlemania-6
18. "TJR: WWE WrestleMania 6 Review" — TJR Wrestling. https://tjrwrestling.net/review/wwe-wrestlemania-6-review/
19. "Ted DiBiase Says He & Jake Roberts Stole The Show At WrestleMania 6" — 411MANIA. https://411mania.com/wrestling/ted-dibiase-jake-roberts-stole-show-wrestlemania-6/
20. "Jake Roberts – 'It Was Never My Idea To Try To Steal The Show At WrestleMania 6'" — eWrestlingNews. https://www.ewrestlingnews.com/news/wwe/jake-roberts-it-was-never-my-idea-to-try-to-steal-the-show-at-wrestlemania-6
21. "This time, you will be the one that grovels for the money" — Cagematch Promos Database. https://www.cagematch.net/?id=93&nr=103
22. "Jake The Jail Bird" — UPI Archives, July 8, 1989. https://www.upi.com/Archives/1989/07/08/JAKE-THE-JAIL-BIRD-Jake-the-Snake-has-been/1808615873600/
23. "The Tragic Real-Life Story Of Jake 'The Snake' Roberts" — Grunge. https://www.grunge.com/127895/jake-the-snake-roberts-tragic-real-life-story/
24. "'Million Dollar Man' Ted DiBiase's Transformation from WWE Superstar to Minister" — Bleacher Report. https://bleacherreport.com/articles/2641220-million-dollar-man-ted-dibiases-transformation-from-wwe-superstar-to-minister
25. Royal Rumble (1990) — Wikipedia. https://en.wikipedia.org/wiki/Royal_Rumble_(1990)

Further Listening

• The Snake Pit with Jake Roberts — Roberts' own podcast retelling of the WrestleMania VI match and his read on the DiBiase feud
• Everybody's Got A Pod with Ted DiBiase — DiBiase's side of the same story, including his 'we stole the damn show' line
• Every Man Has His Price: The True Story of Wrestling's Million-Dollar Man (Ted DiBiase autobiography) — DiBiase's account of the character, the belt, and the personal toll of the era
• The Price of Fame (Ted DiBiase) — DiBiase's later book on faith, family strain, and recovery from the excesses of this period