Demystifying Undertaker’s Legacy at Retirement, His Many Marriages and Facts About His Children

Mark William Calaway is one of the biggest stars in wrestling, but no one would recognize him with that name, he goes by The Undertaker – The Dead Man. Considered as one of the greatest wrestlers, one of his many notable achievements is being the second wrestler with the highest amount of pay-per-view numbers; this is because of the over 170 fights he has participated in.

His wrestling spell is not the only interesting thing about his life as his marriages have also been a focal point of interest. Despite his portrayal as a savage wrecker in the ring, The Undertaker is a family man who has been married three times and fathered four children. After he retires from wrestling, he is expected to enjoy more family time with his offsprings and wife.

Has The Dead Man Really Retired?

For now, nothing is official as both The Undertaker and WWE are yet to make an official statement on his retirement. Howbeit, his recent comments suggest the legend is ready to draw the curtain on his illustrious career spanning more than three decades.

He hinted at his imminent retirement on June 21, 2020, while the last episode of the Undertaker: The Last Ride documentary was underway. According to him, there’s nothing left to prove after three decades in wrestling. He equally made it clear that his desire to step in the ring has greatly diminished.

While admitting that retirement is at hand for him, Undertaker did not rule out the possibility of a comeback in the future which we totally agree with. Meanwhile, tributes are already coming in for the WWE legend.

Wrestlers and other public figures are paying their respect to him on their social media pages.

The Legacy He Leaves Behind Is One For The Ages

A career that started with World Class Championship Wrestling in 1987 and later moved to the WWE in the 1990s has turned into a world-class legacy that the world will not forget in a hurry.

His original character depicts a Western mortician dressed in a trench coat, black Stetson hat, grey gloves, and boot spats. With this persona, he has made a lasting name in the ring. Over time, he has attained a spot among the greatest wrestlers of all time.

A 2013 Digital Spy poll voted him the greatest WWE wrestler to ever grace the ring. IGN named him the second greatest wrestler ever and according to the game and entertainment media outfit, Undertaker is a well-respected player in the wrestling world. Luke Winkie of Sports Illustrated, on the other hand, placed him on the 5th spot on the list of greatest wrestlers of all time.

Two matches he had with Shawn Michaels at WrestleManias XXV and XXVI, received critical acclaim. The acclaimed matches also won the Pro Wrestling Illustrated and Wrestling Observer Newsletter awards for Match of the Year in 2009 and 2010, respectively.

Fellow wrestlers have great respect for the wrestling legend. Big Show proclaimed The Undertaker as the greatest professional wrestler of all time. Mark Henry and WWE chairman Vince McMahon are proud to call him their favorite while WWE Hall of Famer, Jim Ross, has this to say: “Without question, The Undertaker is the greatest big man in the history of wrestling… There is no greater WWE star ever than The Undertaker”.

The Undertaker character has also gained recognition in the prestigious Guinness World Records Gamer’s Edition. He entered the record as the wrestler with the most consecutive victories at WrestleMania in 2016. The previous year, Tom Fordy from Telegraph called The Undertaker “the world’s greatest sportsman”.

All in all, The Undertaker is a seven-time world heavyweight champion in WWF/E. So far, he has held the WWF/E Championship four times while holding the World Heavyweight Championship three times.

A Breakdown of His Championships and Recognition From Different Outfits

The Baltimore Sun

  • Feud of the Year (2007)
  • Match of the Year (2009)
  • Match of the Year (2010)
  • Pro Wrestling Illustrated
  • Comeback of the Year (2015)
  • Feud of the Year (1991)
  • Feud of the Year (2015)
  • Match of the Year (1998)
  • Match of the Year (2009)
  • Match of the Year (2010)
  • Match of the Year (2012)
  • No. 2 of the top 500 singles wrestlers in the PWI 500 in 2002
  • No. 21 of the top 500 singles wrestlers of the “PWI Years” in 2003

United States Wrestling Association

  • USWA Unified World Heavyweight Championship (1 time)

World Class Wrestling Association

  • WCWA Texas Heavyweight Championship (1 time)

World Wrestling Federation/Entertainment

  • WCW Tag Team Championship (1 time) – with Kane
  • World Heavyweight Championship (3 times)
  • WWF/WWE Championship (4 times)
  • WWF Hardcore Championship (1 time)
  • WWF World Tag Team Championship (6 times) – with Stone Cold Steve Austin (1), Big Show (2), The Rock (1), and Kane (2)
  • Royal Rumble (2007)
  • Tuwaiq Mountain Trophy (2020)
  • Slammy Award (12 times)
  • Best Entrance Music (1997)
  • Best Tattoo (1997)
  • Match of the Year (2009, 2010, 2012, 2015)
  • Moment of the Year (2010) vs. Shawn Michaels at WrestleMania XXVI
  • Most Intimidating (1994)
  • OMG Moment of the Year (2011)
  • Rivalry of the Year (2015) vs. Brock Lesnar
  • Star of the Highest Magnitude (1997)
  • WWF’s Greatest Hit (1996)

Wrestling Observer Newsletter

  • Best Gimmick (1990–1994)
  • Best Heel (1991)
  • Feud of the Year (2007) vs. Batista
  • Match of the Year (2009) vs. Shawn Michaels at WrestleMania XXV
  • Match of the Year (2010) vs. Shawn Michaels in a career vs. streak match at WrestleMania XXVI
  • Worst Worked Match of the Year (2001) with Kane vs. KroniK at Unforgiven
  • Worst Match of the Year (2018) with Kane vs. Triple H and Shawn Michaels at Crown Jewel
  • Most Overrated (2001)
  • Readers’ Least Favorite Wrestler (2001)
  • Worst Feud of the Year (1993) vs. Giant González
  • Most Disgusting Promotional Tactic (2005) Terrorist angle on the day of London bombings
  • Wrestling Observer Newsletter Hall of Fame (Class of 2004)

What The Undertaker Plans To Do Post-Retirement

Despite the massive popularity he commands, The Undertaker has not been one to bask in the glory of it all by going into movies like fellow wrestling superstars – John Cena or Dwayne “The Rock” Johnson.

In a recent interview with BBC in May 2020, the legend told the media outlet that though the opportunities have been available for him, he just doesn’t like the idea of becoming a Hollywood star. “Wrestling and WWE is my passion. It’s where I’ve completely invested and where my heart is at,” he maintained.

Nevertheless, he has made a few appearances in not less than ten TV series and movies to date. His debut role as an actor is in the film Suburban Commando (1991), Hulk Hogan also starred in the American science fiction comedy. Before the 1990s came to an end, he appeared as himself in the documentary Beyond the Mat and also played Soul Chaser Demon in two episodes of Poltergeist: The Legacy, all in 1999. The same year, he portrayed himself in Downtown and Celebrity Deathmatch.

His voice has also been featured in animated films like The Flintstones & WWE: Stone Age SmackDown! (2015), Scooby-Doo! and WWE: Curse of the Speed Demon (2016), and Surf’s Up 2: WaveMania (2017). His latest TV appearance is in Undertaker: The Last Ride.

For now, it is not clear what The Undertaker plans to do with his time after retirement but one thing is clear, he is grateful to have a family to go back to.

The WWE Superstar Has Been Married Three Times

Among the three women he married, only one is not involved in the wrestling world and that was his first wife. He married her when his career was just taking off.

Jodi Lynn – 1989 to 1999

  • Full name: Jodi Lynn Calaway
  • Date of birth: Not known
  • Occupation: Not known

Among Undertaker’s wives, the first was Jodi Lynn, the two got married in 1989 which was the same year he joined the Wrestling World Entertainment (WWE). Of all the women he has dated, she is the only person who was not involved in wrestling but this did not stop their love from blossoming. Both of them did not want her to have anything to do with his job, and she was more comfortable staying home.

The private life they led during their ten years as husband and wife made it hard to trace any public appearance made by the two. During this time, they welcomed their only child, Gunner Vincent who was born in 1993. But things went sour in the marriage by 1999, the same year they went their separate ways.

In the course of his career, Undertaker has made enemies, as well as friends, and one of the people he was closest to in his early career was Brian Lee. Lee, however, had other plans for their friendship; it was revealed that Lee and Jodi started to have an affair. When The Undertaker found out, he filed for divorce and in May of 1999, the couple was officially divorced. For his actions against Calaway, Lee was kicked out of the WWE.

Sara Frank – 2000 to 2007

  • Full name: Sara Chirie Frank
  • Date of birth: July 21, 1977
  • Occupation: professional wrestler

Not long after his first divorce, he got married again. The next woman Mark Calaway exchanged vows with was Sara Chirie Frank, it is not known how they met but her marriage to Calaway was helpful for her professionally as she got to make appearances with him in the wrestling world in 2001, a year after they got married. Sara was also part of the feud storyline that existed between her husband and Diamond Dallas Page, another wrestler.

Unlike his first marriage which lasted a decade, his marriage to Sara only lingered for seven years; but in that time, The Undertaker got a tattoo of her name across his chest and the two of them started a fund for providing treatments to dogs. Their fund is called The Zeus Compton and it is still operational to date.

Sara and Mark have two daughters together. The first of the two, Chasey, was born in 2002 while Gracie was born in 2005. Two years after the birth of Gracie, the couple got divorced. By 2010, he was married for the third time, this time it was to Michelle McCool.

Is He Still Married To Michelle McCool?

  • Full name: Michelle Leigh Calaway
  • Date of birth: January 25, 1980
  • Occupation: professional wrestler
  • Years active: 2004 to 2011
Undertakers Wives
Undertaker and McCool – image source

A lot of speculations have been going rife about Undertaker’s third marriage. Nevertheless, the WWE legend is still enjoying marital bliss with Michelle.

The two wrestlers got married in 2010; this was four years after they started dating in 2006. Then, McCool was still married to her ex-husband, Jeremy Alexander, who she had been dating since she was in high school. In the same year she divorced Jeremy, she also got married to Calaway which only fueled the rumors of extra-marital affairs.

McCool and Calaway met on the job as she was a professional wrestler who was active from 2004 to 2011. When she started to date The Undertaker who was already a veteran at that point, it was rumored that their relationship existed because of her desire to go up the professional ladder as a wrestler. But she had been a part of the industry for two years at that time. There is however no way it can be denied that her career improved after they began dating.

The couple welcomed their first child Kaia Faith in August of 2012, which was a year after she retired from wrestling. The couple is still together and it is not uncommon to find Michelle by the ringside when her husband makes WWE appearances.

Meet The Undertaker’s Children

His three marriages produced four children for the wrestling superstar and they seem to be the light that brightens his world.

Gunner Vincent Calaway

Gunner is Undertaker’s first child whom he had with his first wife. He was born in 1993 before the marriage packed up. Gunner studied at Full Sail University where he bagged a degree as a Video Game Artist and it seems to be where his interest lies.

Contrary to popular belief that he might follow his father’s footsteps, the younger Callaway seems to have no interest in the sport. Howbeit, he admitted that in his younger years, he was sure he would give wrestling a try but when he entered his twenties, his priorities took a different turn.

Chasey Calaway

On 21 November 2002, the Undertaker and his second wife, Sara, welcomed their first child named Chasey. Aside from the spotlight which she enjoys due to her parents, Chasey is not involved in any known activity in terms of career.

An Instagram post she shared in 2014 suggests she battled cancer.

Gracie Calaway

Roughly three years after the birth of Chasey, The Undertaker and his second wife welcomed another daughter and named her Gracie. She was born on May 15, 2005, and just like her sister, Gracie is not active in the public domain. As such, much is not known about her.

Kaia Faith Calaway

image source

The last of Undertaker’s children is Kaia who is his only child with Michelle McCool. Kaia was born in 2012, two years after her parents became husband and wife.

None of Undertaker’s offsprings is showing signs of following in his footsteps to carry on the legacy he has built.

Obianuju O
Obianuju O
With over several years of professional writing experience, I consider myself an expert storyteller with a passion for connecting with audiences through the power of words. I specialize in creating engaging content for biographies, entertainment websites and other forms of visual media.


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