What if … Brandon Webb had stayed healthy? (2024)

Every Wednesday, The Athletic’s MLB writers will be looking at a key what-if scenario from a different team’s history. This week: The Arizona Diamondbacks.

Bryan Price remembers Brandon Webb’s last comeback attempt.

It was the fall following the 2012 season, nearly four full years since Webb had last pitched in a major-league game. Back then, in 2008, Price had been the Diamondbacks’ pitching coach and Webb had been his ace, a right-hander who’d posted a 3.13 ERA and averaged more than 230 innings a season over his last three campaigns. He’d earned one Cy Young Award and two second-place finishes in that span. But now Webb, only 33 years old, looked nothing like that guy.

Persistent shoulder problems had cost him his career. There had been one surgery and then another. Nothing seemed to fix it. He was theoretically healthy this particular fall, which is why Webb reconnected with Price, who was then with the Reds, to work on his delivery in Phoenix. But too much had changed. His arm action was off, “probably a byproduct of trying to find a way to throw without pain,” Price said. The pair played catch and tried to work on Webb’s mechanics, but when the time came for Webb to throw off a mound, the discomfort was too much to overcome.

“He just couldn’t get over that hump,” said Price, now the pitching coach with the Phillies. “That’s when he finally came to terms with the idea that he wasn’t going to pitch again.”

Webb’s six full seasons in the majors is one of the great unfinished careers in recent baseball history. He was dominant when he debuted at age 24 in 2003 and he became only more fearsome as the years passed. The pitcher who took the mound for the Diamondbacks in 2008 was perhaps the very best in the game at the time, a man in the prime of his career with years of excellence ahead of him. To say he was on a Hall of Fame trajectory is not a stretch.

But then, like a song that cuts off mid-chorus, his career was jarringly over. After a troublesome Opening Day start in 2009, Webb hit the injured list with a shoulder problem and never again pitched in the majors. For years afterward, Webb would watch baseball enviously. “I’d be like, ‘Dude, I should be playing right now. I could be playing right now,’” he said. Even now, at 41 and long at peace with how his career ended, even Webb wonders what many others do:

What if Brandon Webb had stayed healthy?

The first, obvious answer is that Webb would have gotten paid.

As it was, the right-hander earned several million more than anyone with the benefit of hindsight would have given him. At the end of the 2008 season, Webb was halfway through a four-year contract extension he signed prior to the 2006 season. He was entering the final guaranteed year of the deal and would earn $6.5 million in 2009, and the team had what appeared to be a no-brainer club option for 2010 worth $8.5 million with a $2 million buyout — the buyout amount inflated from $500,000 thanks to his Cy Young Award finishes.

The Diamondbacks picked up that 2010 option, even though Webb pitched only four innings in 2009 and was coming off shoulder surgery. To understand why, it’s important to remember that Webb’s shoulder didn’t explode like a popped balloon as much as it just slowly deflated. Even after Webb missed almost the entirety of the 2009 season, nobody thought he’d thrown his last big-league pitch.

The shoulder had started hurting Webb early in the offseason after the 2008 campaign, which he finished with a 3.30 ERA and a 1.196 WHIP. “It usually takes three weeks of non-throwing to be like, ‘Oh, yeah, all right. My arm’s feeling pretty good again. I can tell I took a rest,’” Webb said. “I never really felt like that.” That feeling lingered into the following spring. Catchers and hitters told him his power sinker didn’t look the same, but Webb shrugged it off. He’d had bad springs before. Even when he removed himself early from a B-game on the backfields in his last tune-up for Opening Day, he refused to let himself think it was serious. He assured the team he’d be on the mound to start the season. “I don’t know if I was lying to them or lying to myself or both,” he said.

Webb did make that first start, but he bowed out after four rough innings and landed on the injured list with a shoulder problem that would become a persistent and insurmountable obstacle to his return. Even though the end of his career seemed sudden — he pitched Opening Day and then never again — it wasn’t. Doctors who examined Webb saw wear and tear but nothing seriously wrong. He rehabbed the shoulder through most of the 2009 season before ultimately having surgery performed by Rangers surgeon Dr. Keith Meister. The procedure was a debridement, the removal of damaged tissue, but there was no actual repair being done. “Debridement’s not nothing,” said Webb’s agent, Jonathan Maurer, “but it’s not something that’s career-ending generally.”

Most thought Webb would pitch again, which is why the Diamondbacks picked up Webb’s option for the 2010 season just like they would have if he’d never gotten hurt. Had he remained healthy after 2008, Webb would have been staring down a huge payday once his contract expired. He would have needed two more stellar years in 2009 and 2010 — and there was little indication a healthy Webb couldn’t have provided them — and he would have hit the open market. He would have been heading into free agency as a 31-year-old in a game that hadn’t yet stopped paying guys in their early 30s. As Webb said he thought to himself in 2008 when talks of another extension petered out, “I’ll just go out there and kill it next year and clean up.”

Wondering what Webb would have commanded in free agency takes a lot of conjecture, depending on how he might have performed in the two years he ultimately didn’t pitch, but this what-if scenario doesn’t actually require that guesswork. Those abandoned extension talks provide the answer. Had Webb remained healthy, according to his agent, he never would have hit free agency in the first place.

After he was injured, reports surfaced that the Diamondbacks and Webb had been talking about a three-year, $54 million extension before insurance issues scuttled the deal. But Maurer says the Josh Byrnes-led front office ultimately resolved that issue, finding a firm that would insure Webb. “That deal did get approved,” Maurer said. “The insurance was taken care of.” All Webb had to do, the agent said, was successfully get through his Opening Day start against the Rockies to kick off the 2009 season. “We were signing the deal,” Maurer said. “Everybody had agreed to it.”

That the deal hinged on what literally was Webb’s final big-league start makes our hypothetical much more concrete. Had Webb remained healthy, he would have signed an extension that Maurer said supplanted the 2010 option year and continued for three more, with an average annual value of around $18 million. In 2011, the earliest year the sports salary website Spotrac.com tracks, that would have tied Webb with Barry Zito for sixth among the highest-paid pitchers in baseball. The company he would have been keeping — Cliff Lee, CC Sabathia, Johan Santana, Roy Halladay — would have been fitting peers. Halladay is in the Hall of Fame, and there are cases to be made for the inclusions of Sabathia and Santana.

There would have been one to make for Webb as well.

One spring before Webb got hurt, fellow Diamondbacks starter Dan Haren pointed out that Webb was on a pace to make the Hall of Fame. Ever unassuming, Webb reminded Haren just how difficult it is to be that good for that long. It’s a sentiment he echoes now. “I only played six years. I needed at least four more years to even get on the ballot,” Webb said. “That’s four years to even be considered. I’d probably have to have another six or eight years doing that. That’s tough.”

Tough, but not impossible and perhaps not even unlikely. As a favor to The Athletic, Dan Syzmborski, the creator of the ZiPS projection system at FanGraphs, ran a projection for the rest of Webb’s career following the 2008 season that assumed he remained healthy. It predicted Webb would have again been dominant in 2009 to the tune of a 3.18 ERA and 5.5 fWAR, and then very good for the final three years of his would-be extension — a 3.26 ERA and 14.3 fWAR. Szymborski’s projection carries Webb through the 2020 season, when he’d be pitching at age 41, although with diminishing innings totals as he ages. In the end, he winds up with a career total 70.3 WAR. Webb retired with 29.6.

Such a total would have put Webb squarely in Hall of Fame territory. The average Hall of Fame pitcher has 69 WAR, according to Baseball-Reference. Even if Webb hadn’t pitched into his 40s as the projection assumes, his WAR total likely still would have been good enough. John Smoltz made it with 66 WAR and Halladay got in with 65. Mariano Rivera, one of the few full-time relievers in the Hall, had 56 WAR. Of course, projection systems like ZiPS aren’t ironclad, but they’re also very conservative by nature. That one loved Webb’s chances this much says a lot about how consistent the righty was before his injury.

And there are plenty of reasons to think Webb’s dominance would have continued. For one, he had a lethal pitch that few other pitchers ever mastered — a true sinker. Webb picked up the pitch early in his minor-league career, but the movement he created with it was the product of purely natural ability. “He had a generational sinker,” Price said, “a specialty pitch that for a pitching aficionado, there’d be nothing like sitting behind home plate, but maybe even better, sitting at home and watching through that center field camera and watching the ball do what it did.” Webb threw the pitch more than 80 percent of the time. All hitters could do was beat it into the ground for easy groundouts. Said Maurer, “There are very few pitchers in this game who can in essence throw one pitch, tell everybody it’s coming and still be a Cy Young candidate.”

Sinkers and two-seamers were more prominent in Webb’s day, but have since gone out of fashion in favor of high four-seamers as hitters have reconfigured their swings to hit more home runs. But the majority of Webb’s career would have missed that era, which began in earnest in 2016 and 2017, and even if it didn’t, there’s reason to think his sinker would have remained effective. Sinkers like that don’t suddenly become hittable. Yankees reliever Zack Britton throws a similar straight-down sinker almost exclusively and is one of the best relievers in the game. What’s more, the longer Webb would have pitched, the more effective defenses would have become at positioning themselves behind him. “You could make an argument that he’d be better now in his prime than even back 13, 14, 15 years ago,” Price said. Webb concurs, in his typically understated way. “I should have been OK,” he said.

And even if Webb had to adjust, Maurer thinks he could have. The agent remembers one start against the Giants later in Webb’s run with the Diamondbacks in which the right-hander racked up double-digit strikeouts. That was odd for Webb, whose game was geared toward contact. Afterward, Maurer asked how he’d done it. Webb explained that nothing had been working in his warmup, so he goofed around with a slider — a pitch he’d never thrown — and decided to use it in the game.

“That’s how unbelievable he was,” Maurer said.

Webb still doesn’t know exactly what caused his shoulder to give out. Given his prodigious innings totals, he figures it was simple wear and tear. At the time, it was an injury that mystified everybody. The Diamondbacks thought he’d make it back. So did the Rangers, who signed Webb for one year and $3 million for the 2011 season. It was their orthopedic surgeon, Meister, who’d performed his surgery in the first place. He would have known if there was a dire issue.

“He went to Double A and was throwing 84-85 (mph),” Maurer said. “I remember a conversation with (Rangers general manager Jon) Daniels and him saying, ‘He still has the Brandon Webb sinker. If he can get to 87-88 as his top fastball, he can pitch for 10 more years because of that pitch.'”

Instead of another decade of excellence, Webb has been out of the game. His shoulder deprived him of a rich extension and a legendary career, one that would have made him the Diamondbacks’ first and, to date, only homegrown Hall of Famer. It deprived Arizona of a one-two punch atop their rotation that might have been second in team history to only the combo of Randy Johnson and Curt Schilling.

A healthy Webb likely wouldn’t have changed much about Arizona’s awful 97-loss season in 2010, but having a healthy and dominant Webb certainly would have been a boost in 2011, when the Diamondbacks won 94 games and the division but lost to the Brewers in the first round of the playoffs. Haren was gone by then, traded in the midst of the dour 2010 season by new general manager Kevin Towers, but perhaps still having Webb would have enticed the Diamondbacks to keep the top of Arizona’s rotation intact.

At the very least, Webb would have finished his career with his No. 17 retired alongside Randy Johnson’s No. 51 and Luis Gonzalez’s No. 20 above the seats in right field at Chase Field. (That would also mean current manager Torey Lovullo would need to find a new number.) There’s an argument that Webb’s number should be up there already. Though Johnson’s numbers are unassailable, Webb and Gonzalez have roughly equivalent WAR totals. Webb has the advantage in Baseball-Reference’s calculation, 33 to 30. Gonzalez is favored by FanGraphs, 33.7 to 29.6. Notably, Gonzalez spent eight full seasons in Arizona while Webb spent only six.

Even the most cursory examination reveals Webb’s career as criminally underrated. Had Webb stayed healthy, his former pitching coach thinks, it wouldn’t have been.

“Had he been able to continue to pitch,” Price said, “I think he’d be as much a household name a lot of those other guys who pitched in his generation.”

(Photo: Jonathan Willey / Arizona Diamondbacks/MLB via Getty Images)