It is a tough thing to say how long someone should hang around the wrestling business, and particularly in World Wrestling Entertainment. Stay on too long, and you run the risk of the audience burning out on you and exhausting the creative possibilities of your character. For main event talents, the worst outcome of all may be a veteran’s long tenure coming at the expense of his legacy. Think about it. A guy is widely respected and at the top of his game from a kayfabe perspective. Given enough years, his body will begin to fail and his skills will diminish. Alternatively, he might fall out of favor with management. The result is a guy with main event credentials being remembered just as well for his mid-card work. And then there are those mid-card guys themselves—guys who might have the chance to thrive somewhere in the wrestling world, but hit a glass ceiling in WWE and wither on the vine—never realizing the upper limits of their potential.

It’s a mistake to hang around too long, but then there are those guys on the opposite side of the line. Some guys leave long before they’ve accomplished all that they might in WWE, burning out on the intense schedule or getting impatient waiting for their big push to come. These are the guys that make fans wonder what if, because there’s always a sense we missed out on the very best they might have had to offer. This article looks back at ten wrestlers who stayed in WWE too long and ten who left too early.

20 20. Stayed Too Long: Chavo Guerrero, Jr

The Guerrero family is legendary in the wrestling world. In their generation, Eddie and Chavo, Jr broke new ground, performing well at WCW and making their way to greater stardom at WWE. While Eddie broke the glass ceiling and became a world champion, that was never in the cards for Chavo in the biggest wrestling company in the world.

Chavo’s supporters might say that this is due to the prejudice against smaller wrestlers. Others might say he just did not have the right overall package to become a main eventer. Regardless, I think we can all agree that he deserved better than months of feuding with Hornswoggle in a comedy feud, dressing up as an eagle to play Jack Swagger's mascot, and years of wallowing in the lower card. While Chavo had a few bright spots teaming with his uncle Eddie and winning the ECW championship, overall, he squandered his prime and a decade of his life underutilized at WWE, when he might have had a shot at becoming the top dog in a company like TNA or ROH.

19 19. Left Too Early: MVP

MVP debuted as a blue chip prospect heel, who worked a smooth, arrogant style. Later, he became a rougher face who hovered around the upper mid-card for a spell. Unfortunately, over the course of about five years with WWE, he never got to that next level and had a truly great match, or a meaningful shot at the main event.

While I get the man not wanting to wither on the vine in WWE, but rather test his fortunes abroad and with smaller companies, he’s a guy who may have gotten his shot at a higher profile position had he hung around longer. With his charisma, and his talents that improved over time, he could have lived up to his moniker and become one of the promotion’s most valuable talents.

18 18. Stayed Too Long: Billy Gunn

Billy Gunn spent 11 years in his first run with WWE. You can’t blame the guy, because he did advance his career and surely made a good bit of money, especially as the company transitioned to the Attitude Era. Gunn peaked, though, as half of The New Age Outlaws, and as a cog in the Degeneration X machine. After a failed main event push that saw him win the King of the Ring tournament and challenge The Rock, Gunn may have remained a respected veteran backstage, but was never taken seriously as an act again. He spent the years following the Attitude Era as a jobber to the stars and bouncing between tag teams with The Big Show, Bob Holly, and most memorably a pseudo-homosexual pair with Chuck Palumbo.

By the time Gunn did leave WWE, the mainstream wrestling audience was more than burned out on him, and he was a shell of his former self. Mind you, even in his 40s he was still an impressive athlete, but he was too old to get main event run elsewhere at that point.

17 17. Left Too Early: AJ Lee

AJ Lee was something of a harbinger of the 2015 Divas Revolution. Before it was in vogue, she wrestled a serious, technical style. Moreover, she rejected the Diva moniker and the culture of Total Divas in favor of wanting to be respected as a wrestler, with no women’s asterisk by her name.

Lee left WWE and announced her retirement from wrestling at the age of 28. Little could she have known that WWE wouldn’t only have Paige to carry on her legacy, but Charlotte, Sasha Banks, Becky Lynch, Bayley, and Alexa Bliss were on their way to usher in a new era. They have put on top-notch matches and get Raw and Smackdown main events (not to mention one PPV main event). Lee could have been awesome contributor to this new class of women.

16 16. Stayed Too Long: Tito Santana

Tito Santana was a loyal company man for WWE, who, cumulatively, worked over 12 years with the company including a run that started before and ended after Hulk Hogan’s main run with the company. He went from an upper mid card guy to a tag team specialist to a jobber to the stars.

While you have to respect Santana’s longevity and loyalty, he is also the kind of guy who saw his stock fall due to crowd fatigue and WWE not knowing what to do with him. Rebranding him as El Matador was a last stab at making him relevant in the early '90s. Santana probably would have been better served, though, to remove himself from the WWE audience for a bit, come back fresh to finish his career in the mainstream on a higher note.

15 15. Left Too Early: Wade Barrett

Wade Barrett looked as though he had all the tools to thrive in WWE. He was a big, musclebound guy, who was also a great talker. He proved himself as an above average in ring worker, too. The main problem for Barrett was that he seemed to keep getting injured, often at inopportune times to mess up whatever push he may have gotten.

In a sense, you can’t blame Barrett for leaving the company. He saw his status slip from main eventing early in his main roster run to becoming a non-featured player in the directionless League of Nations stable. Just the same, you have to believe if he stayed around and stayed healthy, WWE would have done more with him. In his Bad News Barrett gimmick, he connected well with the crowd, and it’s a shame we didn’t get to see what he might have done with a face run before he walked from WWE.

14 14. Stayed Too Long: Jack Swagger

Few guys has a more up and down decade with WWE than Jack Swagger. He was a World Heavyweight and ECW Champion, true. But he also spent inexplicably long periods off TV, and found himself yo-yoed from upper card threat to a lower card talent who no one seemed to care about.

This past March, Swagger reported on Chael Sonnen’s podcast that he had asked for his release from WWE. The move seems overdue, given the company has done so little to take him seriously for close to four years at that point. Fortunately for Swagger, with his size, athleticism, and real life amateur pedigree, and still in his mid-30s, he may still have time to thrive abroad or with smaller wrestling companies. Still, he may have been better served to have traveled a path like Drew McIntyre—leaving younger, killing it on the indies, and coming back a more valuable star.

13 13. Left Too Early: Lance Storm

Lance Storm is one of the greatest professional wrestlers—particularly from an in ring perspective—of his generation. It’s a shame that so few fans know it. While Storm succeeded in ECW and got a decent push in the upper mid card in WCW, when he made it to WWE he didn’t get much in the way of big opportunities over the course of his four year tenure. He left WWE in 2005 and mostly retired from wrestling, only working sporadic independent shows. Though he was only in his mid-thirties, he nonetheless settled into focusing on training newer wrestlers.

There’s something to be said for Storm’s approach. By all accounts his real life personality isn’t so different from his wrestling persona—serious and practical. He saved money, kept his nose clean, and was able to comfortably transition away from full time wrestling before suffering any debilitating injuries. Just the same, you have to wonder if a guy of his talents might have wound up with a significant push, at least on the WWE ECW brand, had he stuck around a few more years.

12 12. Stayed Too Long: Mark Henry

Mark Henry has had a two-decade plus run with WWE. After getting a top dollar contract for a 10 year deal, Henry was considered something of a bust when he only turned out to be a mid-card guy. Interestingly enough, around the end of it was after his original deal was up that the guy finally blossomed, first the top heel for WWE’s version of ECW, then going on a tear as SmackDown’s top villain, in a run that included him crushing Randy Orton, The Big Show, and Kane. After a feud with Ryback, Henry faked his retirement only to parlay all that attention into one more main event program opposite John Cena.

Nearly four years have passed since the Cena program, though, and Henry is still around. He went from a bust, to a celebrated surprise superstar, only to revert back to just another lumbering big man, who flip flops between heel and face alignment to put over whichever rising main event talent needs a push. While Henry is probably still a lock to eventually get inducted into the WWE Hall of Fame, he’s also finishing up his career on a low note. Unlike The Undertaker or The Big Show—big men WWE has gone to great lengths to keep special in the twilight of their careers, Henry is looking like just another guy.

11 11. Left Too Early: Beth Phoenix

Beth Phoenix is one of the most impressive raw athletes the WWE women’s roster has ever seen. In particular, she was a great worker with tremendous physical strength. Over six years with the company, she had a successful run, mostly as a heel but also with some face moments, and collected four championships along the way.

Phoenix retired young to start her family—she has now has two children with fellow WWE legend and Hall of Famer Edge. While you can’t knock Phoenix for putting kids first, you also have to wonder how much more she might contribute in the contemporary WWE landscape. Might she be a powerhouse foil for Nia Jax. Or maybe be the dominant physical force to really test Charlotte? We’ll never know, but with veterans like Mickie James and Natalya still on the scene, you have to believe there’d still be a place for Phoenix to shine, even today.

10 10. Stayed Too Long: Jerry Lawler

Jerry Lawler is a legend. He’s the definitive icon of Memphis wrestling, and he’s now been an institution in WWE programming for over two decades. His WWE career has seen him go from entering as a respected veteran in the upper mid card to becoming one of the most iconic color commentators in wrestling history. It’s hard to imagine so many great Attitude Era moments, in particular, without Lawler at the announce table.

Time has not been kind to Lawler’s WWE legacy, though. His last in ring rivalry was a largely embarrassing drawn out feud with non-wrestler Michael Cole. Meanwhile, Lawler went from a legit crowd favorite to sounding like a dirty old man in all of the most annoying ways possible for forcing puns and making light of serious situations in the ring. WWE has now relegated him to special appearances and pre-show panels which is probably the best use for him. Lawler’s legacy probably would have been best served if he had at least taking a few-year break from the late 00s to early 10s, if not walking away from the national scene altogether then.

9 9. Left Too Early: Cody Rhodes

Though he tends to get overlooked, Cody Rhodes may be the single best character actor of his generation of professional wrestlers. In the roles of earnest second-generation star, heel henchman, arrogant pretty boy, super villain, and cosmic anomaly, he committed and recommitted himself time and again over the course of nine years on the main roster.

You can understand Rhodes’s decision to leave. He seemed to have stalled as a mid-carder with the Stardust gimmick, and WWE didn’t seem interested in his creative input to take the character to the next level. Just the same, the brand split wound up hitting mere months after he left. While there’s no guarantee, there’s plenty of possibility he might have finally had the chance at a main event push, with twice as many main event opportunities in play.

8 8. Stayed Too Long: Sabu

It feels strange to say that a guy who really only worked for a year with WWE overstayed his welcome with the company. Sabu was an important figure when WWE relaunched ECW, given he was one of the original promotion’s most recognizable stars. It was fun to see him work big ECW reunion shows under the WWE banner. Just the same, once ECW was up and running as a weekly show, it quickly became apparent Sabu was the most meager shell of his former self. Sure, he still looked crazy, but in his 40s he had lost much of the athletic edge that once made him so special.

Interestingly, WWE seemed to revere Sabu to a point, keeping him in a high profile position within the ECW brand and including him in major angles like the ECW Originals vs. New Breed angle. Just the same, watching Sabu began to feel more and more like watching an old dog waiting to get put out of his misery. He wasn’t the kind of act that should have been working a full time schedule, and he arguably tarnished his legacy in the process.

7 7. Left Too Early: Ted DiBiase Jr.

Ted DiBiase, Jr is a real anomaly in the WWE landscape. He is the son of one of the most iconic characters in the history of the business. He had a great, muscular look that made him all fit WWE’s prototype for a star. Add onto that that he came along to be a solid worker and talker, and he got over to a reasonable degree as a featured player in the Legacy stable.

Unfortunately, after Randy Orton soundly defeated DiBiase (and Cody Rhodes), Ted found himself lost in the shuffle as a heel without direction and then as a lower card face. Perhaps reading the writing on the wall, he opted not to re-sign with WWE and to mostly retire from wrestling shortly after. With the emergence of NXT, DiBiase might have been a prime candidate to take a step back, reinvent himself with a new gimmick, and come back strong. Sadly, he left the company when NXT was still in its fledgling stages, and he looks to be gone for good.

6 6. Stayed Too Long: Ric Flair

Ric Flair is widely agreed to be one of, if not the single greatest wrestler of all time. The Nature Boy looked to be on his last legs in the dying days of WCW, and it was a feel good story to see him return to something like his old form in a WWE ring. He seemed to find his true calling, though, when he was mostly a manager and only an occasional wrestler for the Evolution stable. In the aftermath of that group, though, Flair carried on for another three years. While Flair was still a competent worker, he was not the man he once was, and every compliment thrown his way came with the asterisk that he was doing well “for his age.”

When he was pushing 60 years old, Vince McMahon finally pulled the trigger on a retirement angle. Flair purportedly didn’t want to hang up his boots, but followed orders and worked his last program, culminating at WrestleMania XXIV. While the retirement match itself opposite Shawn Michaels was a great one and a proper send off for a legend, it’s a shame that younger fans would only know Flair as an old man who didn’t seem to know when to quit. By all rights, he probably should have stopped wrestling with any kind of regularity a good four or five years earlier.

5 5. Left Too Early: Shawn Michaels

In the mid-to-late 90s, Shawn Michaels established himself as one of the greatest all-around wrestlers of all time, only to see his career get cut short due to a debilitating back injury. Against all odds, the early 2000s saw him get a second chance, when he returned, largely healed, after four years away from the ring. Michaels would another eight years to his career, including all time classics opposite Triple H, Kurt Angle, The Undertaker, and more.

It’s hard to argue against Michaels’s choice to retire when he did. He’d made amends for his bad backstage reputation, he’d given the fans a series of dream matches with a new crop of stars, and he’d left off still more or less at the top of his game.

Just the same, when you look at the contemporary WWE landscape, it’s hard pill to swallow that we’ll never get to see HBK vs. Seth Rollins, AJ Styles, Samoa Joe, or a host of others. I don’t think it would make sense for Michaels to still work a full-time schedule at this point, but as visiting special attraction, there’d still be plenty of magic for Mr. WrestleMania to make happen.

4 4. Stayed Too Long: Curtis Axel

Curtis Axel is the son of “Mr. Perfect” Curt Hennig, and it may surprise you to know that he’s been on the WWE main roster for most of the last seven years, not to mention that he’s been under WWE contract for close to a decade. Over that period of time, guys tend to accumulate moments. Big wins. Memorable segments. Axel did get one small push back in 2013, when he re-debuted under his current name. He proceeded to rack up indecisive wins over Triple H and John Cena—but they were wins—not to mention picking up the Intercontinental Championship. Rather than foreshadowing big things ahead, however, this was undeniably Axel’s peak in WWE. Over the years to follow he’s ranged from a tag guy to a lower card guy, to a comedic version of either.

By all accounts, Axel is a gifted in ring performer (trusted, even, to personally help The Rock back into ring shape before WrestleMania XXVIII). I won’t deny he has his limitations when it comes to charisma, but on the indies, with the Hennig name, I don’t doubt he could be a main event player. Axel is probably comfortable collecting WWE scale paychecks at this point, but it’s sad to watch his physical prime slip away year by year without a legacy to show for it.

3 3. Left Too Early: CM Punk

Of all the wrestlers in this article, Punk is the one I can say with certainty some would disagree with me listing him. He left WWE bitter, physically injured, and burned out to the point that he had no interest in carrying on with WWE, regardless of money or promises for his future. We could debate the finer points of whether it would have been worth his while to carry on with the company, but I am going to boil this all down to a singular point: the WrestleMania main event.

It has come up in quite a few shoot interviews, that a ‘Mania main event was Punk’s ultimate goal as a WWE performer, and the one milestone he regrets never achieving. Punk was old school in the sense that he’d accept nothing less than the main event—the match with not only top billing but the final spot on the show. The funny thing? Given Daniel Bryan getting forced into retirement, Batista flopping and then leaving after just a four-month stint, John Cena going part time, and the crowd’s resistance to Roman Reigns as the guy, it is entirely possible Punk would have gotten his shot at some point in the last few years.

2 2. Stayed Too Long: The Undertaker

No question that The Undertaker is one of the greatest WWE Superstars of all time, and is rightly respected by his fellow talents, management, and the fans alike based on a nearly twenty-seven-year body of work.

The tough part is that, around the 20 year mark, The Phenom was legitimately still at the top of his game. Though he’d started to work more sporadically, he put on back to back great matches with Shawn Michaels at WrestleManias XXV and XXVI, and followed them up with three more very good WrestleMania matches opposite Triple H (twice) and CM Punk.

Since the Punk match, The Undertaker has not had any particularly good WrestleMania matches. In particular, at WrestleMania 33 it looked like his body had failed him and by the late stages of the match he was uncomfortable to watch.

You can argue The Deadman should have retired after vanquishing Punk in tribute to Paul Bearer, or after his WrestleMania undefeated streak ended a year later. Heck, I could even understand finishing his in ring career with Brock Lesnar in the summer of 2015, because I do feel that story and its matches exceeded expectations. By 2017, however, he wasn’t fun to watch anymore and ran the risk of tarnishing his legacy or, worse yet, seriously hurting himself.

1 1. Left Too Early: Kurt Angle

Kurt Angle has told the story in a variety of interviews, that in 2006 WWE management confronted him about needing to take time off. Angle was dealing with multiple very serious injuries and may or may not have been on the front end of a serious problem with painkillers (if it hadn’t started already, it would soon after). By all accounts, WWE fully intended for Angle to come back and remain a big contributor. By all accounts, Angle had no interest in taking time off.

The result was Angle leaving WWE prematurely and signing with TNA. He would actually wind up with a longer career in TNA than he’d had in WWE, and Angle’s gone so far as to claim that he became a better wrestler.

As an artist, Angle got to keep working and got to have great matches with guys like Samoa Joe and AJ Styles that he probably never would have had had he stuck with WWE. Just the same, his departure means that more than half of his pro wrestling career and all of those great matches were lost on the WWE audience. It’s a shame to think of all the matches and moments Angle might have arrived at in front of a truly national audience had he taken even a year off to get himself right, then carried on with WWE. At least now he’s back in WWE and back to an on-air role to entertain the fans once more.