WTF Happened To Curt Schilling?

How the Red Sox hero went from the top of the world to the bottom of the fever swamps.
Former Red Sox pitcher Curt Schilling campaigned for Donald Trump in New Hampshire during the 2016 election. Massachusetts didn't want to hear from him anymore.
Former Red Sox pitcher Curt Schilling campaigned for Donald Trump in New Hampshire during the 2016 election. Massachusetts didn't want to hear from him anymore.
Jim Davis/The Boston Globe via Getty Images

The sign appeared in a window above Boylston Street as the Red Sox paraded through downtown Boston to celebrate the team’s first World Series title in 86 years.

Schilling/Bush ‘04.

It was a tribute to Curt Schilling, the pitcher who’d been brought to Boston to boost a team that hadn’t won baseball’s biggest prize since 1918 and that had choked away yet another shot at the World Series the year before.

He’d delivered immediately, winning 21 games in the regular season. But it was in the postseason that Schilling became a hero.

The Red Sox had trailed the New York Yankees, their hated rivals, three games to two in the American League Championship Series that October. Although he needed sutures to hold his right ankle together, Schilling took the mound in Game 6. He was built for these moments ― he’d never lost a playoff game when his team was facing elimination. Even as he winced in pain, even as the blood soaked through his white sock, he threw seven innings of one-run ball, and the Red Sox won. A night later, they’d win again. A week later, they were World Series champs.

Sox fans embraced Schilling, the man who had gutted it out. He may just have been popular enough to win a few votes for President George W. Bush that year, even in the Democratic stronghold of Boston.

That sign linked him to Bush ― not the Democratic candidate, Massachusetts’ own Sen. John Kerry ― because Schilling was already an outspoken Republican. While the sign might have been a joke, the idea of him running for office someday didn’t seem that far-fetched ― to him or a lot of people who knew about politics. Baseball had taught him there was nothing he couldn’t do if the rest of the world would just get out of his damn way.

By the time, more than a decade later, that Schilling floated the idea he might challenge another Massachusetts senator, Elizabeth Warren, in 2018, he’d become a laughingstock, a guy who was fired by ESPN for not shutting up and who shared the sort of idiotic memes once relegated to chain emails. He’d thrown himself behind Donald Trump, who was heading toward certain defeat in the Bay State. He’d taken to referring to Hillary Clinton as “Killary” and to her party as “the Demokkkrats.” And he’d landed a daily radio show on Breitbart News Network, the right-wing outlet that welcomed white supremacists and other angry men.

So in October, when Schilling held a rally for Trump outside Boston city hall, perhaps a dozen people bothered to show up. Schilling, arms crossed, hat pulled down over his brow, stood there in the rain. He’d lost his grip on Boston and the world ― and it didn’t make sense.

Schilling became a legend in Boston during the 2004 postseason, when he helped the Red Sox win their first World Series title in 86 years.
Schilling became a legend in Boston during the 2004 postseason, when he helped the Red Sox win their first World Series title in 86 years.
Ezra Shaw/Getty Images

The chances of a high school baseball player being drafted by Major League Baseball are about 0.5 percent, according to Bleacher Report. The great majority of those drafted after the first round will never get out of the minor leagues. The number of players honored in the Hall of Fame is less than half the number who played in the majors just last season. Becoming a potential Hall of Famer requires a loose focus on reality, a stubborn refusal to consider the math that says success is virtually impossible.

Schilling built his reputation on overcoming those odds. He didn’t make his high school varsity team until his senior year, and his next stop was junior college. He was drafted in the second round in 1986 and then spent several years bouncing between the minors and the majors as a reliever. He was traded three times early in his career and only broke through as a starter for the Philadelphia Phillies in 1992, when he was 25. Then he overcame a mid-career lull to lead the expansion Arizona Diamondbacks to the World Series in 2001. By the time he left Boston, he was a 200-game winner with three World Series championships and an outside shot at enshrinement in Cooperstown.

Schilling arrived in Boston with a reputation as a no-nonsense pitcher who did whatever it took to win, and some saw his willingness to pitch through pain — see the Bloody Sock — as reminiscent of baseball’s old-timers. “You simply put their names in the lineup, and then sat back and watched the game,” a Boston Herald columnist wrote.

There’s a sort of coded language in sportswriting, where praise about “grit” and “scrappiness” is often reserved for white athletes. The words draw a contrast, wittingly or not, with black and Latino players, who are described as flashier and more reliant on natural ability. The same code has long had a home in America’s political discourse. So while sports columnists saw Schilling’s pugnacious drive as an asset on the field, politicians like Bush saw his “blue-collar” approach to baseball as an asset on the campaign trail ― primarily by helping them appeal to white, working-class voters.

President Bush’s advisers “shared high-fives,” the Boston Globe reported, when Schilling went on “Good Morning America” a few days after the 2004 World Series victory and urged viewers to “Vote Bush!” The Bush team immediately invited the pitcher to campaign with the president in New Hampshire, where Schilling could bolster the president’s efforts to paint himself as a man of the people. Meanwhile, they were pushing an elitist critique of Kerry, the man who windsurfed off Nantucket. Schilling appeared with Bush in Pennsylvania during the campaign’s final days. He cut radio ads that ran across New England.

Three years later, Schilling hit the campaign trail for another Republican presidential candidate with the same goal in mind. A month after the Red Sox won the 2007 World Series — Schilling went 3-0 that postseason — Arizona Sen. John McCain, the leading candidate for the GOP nomination, brought Schilling on stage in New Hampshire. McCain’s team believed Schilling “personifies the Arizona senator’s grit and determination,” the Globe wrote.

“They’re up in the ivory tower and they’re trying to pass judgment. They said things … that made me realize that they never gave a shit about me.”

- Curt Schilling

Schilling, who had signed a new contract with the Red Sox that October, hoped to pitch one more season in Boston. But he’d already thrown his last Major League pitch. His throwing shoulder began to act up during spring training in 2008. He wanted to have surgery; the team thought rehab would do the trick. Top brass also floated the idea of voiding his $8 million deal if he went under the knife against their wishes. In Schilling’s version of the tale, which he has recounted in multiple radio appearances since, the team accused him of hiding the shoulder injury to get that final contract.

Schilling missed the entire 2008 season and ultimately retired early in 2009. He’s still mad about how his career ended and believes Red Sox management essentially gave up on him.

“They’re up in the ivory tower and they’re trying to pass judgment,” Schilling said of how the team approached his injury in a 2016 interview. “They said things … that made me realize that they never gave a shit about me.”

Schilling and Red Sox owner John W. Henry, according to the pitcher, battled over politics as well. Henry, who endorsed and campaigned with Kerry in 2004, “went nuts” when Schilling endorsed Bush, he said in that same interview.

When Sen. Ted Kennedy (D-Mass.) died six months into Schilling’s retirement, rumors began to circulate that Schilling was being recruited to run for the open seat. McCain told reporters that he had called Schilling to urge him to jump in the race.

Schilling routinely stoked the rumor mill too ― and why not? Politics were a natural fit for the former pitcher. As a player, he’d always craved the sort of attention, positive or negative, that comes with being high-profile. His teammates in Philadelphia had dubbed him “Top Step Schill” and “Red Light Curt,” nods to his knack for finding the camera even when he wasn’t pitching. When the Globe asked Red Sox players about the election in 2004, another pitcher pointed the reporter straight to Schilling’s locker.

“Curt had a large personality and a lot of opinions on a variety of subjects,” Pedro Martinez, Schilling’s co-ace in Boston’s pitching rotation, wrote in his 2016 autobiography, “but I didn’t spend any time listening or reading up on what he was saying to the media. I cared about him as a pitcher.”

Schilling found a reliable sparring partner in Democratic outfielder Gabe Kapler. “Gabe Kapler and I used to have a ton of debates, he’s very liberal,” Schilling said during a Reddit “Ask Me Anything” session in 2016. Kapler was a “top 5 teammate of ALL TIME...even though politically he’s a bit ‘short,’” Schilling tweeted last year.

“The person that works 9-to-5 for crap dollars gets spat on, and [Massachusetts is] becoming a state that’s next to impossible to live and prosper in.”

- Curt Schilling

As his baseball career neared its end, Schilling had increasingly filled his time by airing his political opinions ― through regular segments on Boston-area radio shows and posts on 38 Pitches, the blog that he’d launched to connect with fans and where he began to closely follow the 2008 election. (Thirty-eight was the number he wore throughout his career.)

Schilling often engaged his critics on the blog, but he was not yet a firebrand. He was an “independent” and “will always be,” he wrote in a Sept. 5, 2009, blog post. He had voted for Bush twice and Bill Clinton before that, he said. He wanted lower taxes but was happy to pay his share. He opposed abortion and gay marriage but believed both were “so far beyond the scope or responsibility of one person to legislate it’s laughable.” He was “absolutely for the 2nd Amendment,” he wrote. “But I also think this country has become so beholden to special interest and lobbyists that we have completely sacrificed the safety and well being of the individual American citizen.”

Schilling’s main political position was that “the status quo is not working” for ordinary people. “The person that works 9-to-5 for crap dollars gets spat on,” Schilling said in one interview about his potential candidacy, “and [Massachusetts is] becoming a state that’s next to impossible to live and prosper in, and I think it was anything but when it was founded.”

But Schilling had little patience for far-right theories. In one post, he brushed aside right-wing concerns about Barack Obama’s supposed ties to Bill Ayers, the college professor who had co-founded the violent revolutionary group Weather Underground. The day after Obama won, Schilling congratulated the new president with a hint of admiration for the way he’d campaigned, if not for his politics.

Schilling still seemed, in short, like the sort of Republican who might be able to pull off an upset in deep-blue Massachusetts. Newspapers and their columnists all but asked him to run for the Senate. A poll or two even showed he had an outside shot. And as he outlined his views ahead of a potential campaign, he painted himself the way Bush or McCain might have: as a moderate Republican willing to fight against a broken establishment.

Politics, though, weren’t yet Schilling’s passion, and he ultimately chose not to run for Kennedy’s seat. Instead, he went on the campaign trail again as a surrogate for state Sen. Scott Brown, the Republican choice to pursue the opportunity he’d passed up. Just as Bush and McCain had before, Brown thought Schilling would bolster the working-class, anti-establishment image he’d crafted for himself (Brown made a show of driving a pickup truck and often draped a barn jacket over his suit).

Schilling remained a baseball hero, and his exploits played into the race when the Democratic candidate, state Attorney General Martha Coakley, failed to grasp what the sport means to Bostonians. First, she sneered at the idea of “standing outside Fenway Park … in the cold … shaking hands” with voters. Later, she awkwardly suggested that Schilling was a Yankees fan.

Schilling played it perfectly, with a diplomatic tone that still twisted the knife. “It’s not really that big of a deal,” he told reporters in January 2010. “But again, I think it’s another sign of her aloofness, or just the fact that she’s very out of touch with the people.”

Brown pulled off the upset a few days later.

As the 2016 campaign neared its end, Schilling landed a radio show on Breitbart and suggested that he might even run for the Senate in 2018.
As the 2016 campaign neared its end, Schilling landed a radio show on Breitbart and suggested that he might even run for the Senate in 2018.
Jim Davis/The Boston Globe via Getty Images

After passing on the Senate race, Schilling turned his focus back to 38 Studios, a video game company he’d launched in 2007. A relentless work ethic and boundless confidence (plus his share of good luck) had earned him more than $90 million in 20 years of baseball. Now he dreamed his gaming startup would take him to the next level, making him “Bill Gates rich,” Boston Magazine wrote in 2012.

Schilling was able to attract top-name talent, in part because of his money ― he pledged to finance much of the company himself ― and in part because he was Curt Schilling. His persistence didn’t hurt, either. In 2006, he called Todd McFarlane, an artist known for his work on Marvel Comics’ Spider-Man series and for creating Spawn, among the most popular comic characters ever. He wanted to share his business plan. He even flew McFarlane to Kansas City during a Red Sox road trip to discuss it in person. Schilling offered McFarlane a job as the company’s art director, but the designer didn’t commit on the spot.

A few nights later, McFarlane’s phone rang for what felt like the hundredth time since the meeting. It was Schilling again, and he was whispering.

“Todd, I’m in the locker room,” Schilling said, as McFarlane remembers now. “It’s the fifth inning. I’m not supposed to be making a call.” But he needed to know if McFarlane would take the job.

McFarlane would eventually say yes.

To achieve 38 Studios’ ambitious goal ― the creation of a massively multiplayer online role-playing game ― Schilling would also need more money. In July 2010, the state of Rhode Island agreed to help, giving 38 Studios a $75 million, taxpayer-backed loan guarantee. In return, Schilling moved the company to Providence and promised to create 450 jobs by the end of 2012.

Alas, money, talent and Curt Schilling would not be enough. By 2012, 38 Studios was on the fast track to collapse, bleeding cash with little hope that it could actually produce a game. The company filed for bankruptcy in June of that year.

Schilling had failed, and as he’d done when his pitching days ended, he pointed fingers. He blamed the government of Rhode Island, at least in part. If they’d just given him more time. He turned on Gov. Lincoln Chafee, who had begun to re-evaluate the loan guarantee deal.

“They did everything in their power to make sure this went the way it went,’’ Schilling said later.

“They have been screwed, betrayed by the country they love, discarded like trash on the side of the information superhighway.”

- Michael Kimmel, a sociologist who has studied how angry white men see the world

As 38 Studios collapsed, a presidential election was heating up, once again featuring a Massachusetts politician, former Gov. Mitt Romney. Under different circumstances, Schilling might have made an effective campaign surrogate. Romney, a wealthy Republican venture capitalist, certainly needed help bolstering his connections to the working class, as the Obama campaign hammered him with devastating ads about people who’d lost jobs when Romney’s firm re-organized their companies.

But Schilling’s shine had begun to tarnish. He’d left dozens of people out of work and cost Rhode Island taxpayers more than $100 million ― a fact that had soured much of New England on the former pitcher. His public fights with former employees and with Chafee, as well as the endless media examinations of 38 Studios’ downfall, didn’t help. The Romney campaign didn’t embrace him.

Goodbye, pitching career. Goodbye, gaming empire. Goodbye, establishment camaraderie. Goodbye, fan worship. What had happened to the world as Curt Schilling understood it?

After Obama was elected the nation’s first black president in 2008, social scientists and journalists noted a growing counter-phenomenon: “angry white men” who feel “they have been screwed, betrayed by the country they love, discarded like trash on the side of the information superhighway,” as sociologist Michael Kimmel wrote in his 2015 book.

The defining characteristic of angry white men ― aside from being white and male ― is that they suffer from what Kimmel called “aggrieved entitlement”: the belief that America is “their country” and that it is being taken away from them. Although they’re angry at politicians, bureaucrats and the system writ large, the primary targets of their ire are women, minority groups and immigrants ― the people they perceive as the undeserving beneficiaries of their troubles. Seeking validation of their worth, they turned to “unapologetically ‘politically incorrect’ magazines, radio hosts, and television shows,” Kimmel wrote. And their rage only intensified when Obama was re-elected in 2012. That contest represented “the demise of the white American male voter as a dominant force in the political landscape,” Kimmel wrote. (They showed otherwise in 2016, when Trump won in part because of his strength with white men.)

Schilling fits the pattern almost perfectly. It didn’t matter that baseball had made him a far richer and more privileged man than the middle-class subjects of Kimmel’s studies. Over the two years following the collapse of 38 Studios, Schilling sought out and found answers in the angrier and more paranoid corners of political thought. He started talking more about politics on the radio and social media. His views, at least those he expressed publicly, began to shift further right. He latched on to the Benghazi “scandal” that found fault with every Obama administration decision leading up to and following the deadly attack on that U.S. mission in Libya. His pet cause ― proving that climate change was a fraudulent hoax foisted on the American public ― became an even bigger passion.

Schilling regularly called local radio shows during his playing days to urge fans not to trust sports reporters. After 38 collapsed, he moved on to the idea that news reporters were also peddling “fake news.” Judging from the links he shared, he was reading right-wing sites further and further from the mainstream. And he was isolating himself: “I don’t seek out people I disagree with,” he said in a 2016 interview. “I don’t seek out the content they create. It’s a waste of my time.”

Kapler, Schilling’s old sparring partner in the Boston clubhouse, noticed the shift in 2013, when Schilling posted a link to a story on, the conspiracy-driven site run by Alex Jones:

As Schilling descended into the fever swamps of right-wing politics, one vestige of the old sports hero remained: his job as a baseball analyst at ESPN. He was good at it.

The cable sports network had warned its talent about sharing political views online. Schilling earned his first suspension from ESPN in August 2015 for posting a meme comparing Muslims to Nazis. He kept posting controversial memes even after the suspension, railing against “illegals” and other immigrants and pondering a looming apocalypse. He told a Kansas City radio show that Clinton “should be buried under a jail somewhere” for keeping her emails on a private server.

Then, in April 2016, Schilling crossed ESPN’s line for good. North Carolina’s GOP-controlled legislature had passed a law to bar transgender people from using the public bathrooms that match their gender identity, a move that sparked a nationwide backlash. Schilling chose to repost an image on Facebook that showed a portly man dressed in drag. “LET HIM IN,” it read.

Screengrab via Outsportscom

He was widely criticized on sports news sites. ESPN fired him two days later.

Schilling blamed what he saw as the growing scourge of political correctness and ESPN’s alleged turn toward liberal politics. Never mind that two years earlier, the network had suspended baseball writer Keith Law for defending evolution in a debate with Schilling. Sarah Palin rushed to Schilling’s defense. “ESPN continues to screw up,” she said on Facebook.

Schilling called for Democratic nominee Hillary Clinton to be "buried under a jail" for keeping emails on a private server.
Schilling called for Democratic nominee Hillary Clinton to be "buried under a jail" for keeping emails on a private server.
Jim Davis/The Boston Globe via Getty Images

Untethered from the Red Sox, 38 Studios and now ESPN, Schilling grew louder and louder. He suggested he was planning to run for public office “soon” and laid out an ambitious path: “... state office first, white house in 8 years ... or 4 if by some amazing illegal event this country elects another clinton.”

Schilling initially backed neurosurgeon Ben Carson in the 2016 Republican primary. But soon he threw his weight behind Trump, the candidate who best matched his own bombastic approach and in whom Schilling perhaps saw something of himself. “I realized very quickly this was a man decisive in action and confident in his ability,” Schilling wrote in a blog post announcing his endorsement. “I also realized that regardless of his net worth, he worked his ass off.”

Although Trump never brought the former pitcher on the campaign trail, Schilling became something of a faux surrogate, appearing occasionally on cable to defend the candidate’s positions ― a role he seemed to earn for no other reason than that some viewers might remember him as a ballplayer.

In October, Schilling landed a daily morning show at Breitbart, which had grown into an online behemoth by stoking the fears of the same white voters that politicians had once used the pitcher to reach. Schilling had long believed that someone else ― Red Sox management, the media, Chafee, ESPN ― was standing in the way of his ultimate success. Breitbart was the place where that kind of belief is a founding principle.

“Voters in Amarillo are saying their votes are being changed. Just another day in America, boys. Gosh dang.”

- Curt Schilling, speaking last year on his Breitbart radio show

The site, which was practically a house organ for the Trump campaign, pushed the idea that the American system was broken, especially for white working men, and it blamed immigrants, Muslims, feminists and Obama. In the words of its former chief Steve Bannon, Breitbart was “a platform for the alt-right” ― the white nationalist and racist movements that were supporting Trump.

From the earliest days of his show, which he named “Whatever It Takes,” Schilling espoused the conspiracy theories and racial resentment that fed Trump’s base. The polls that showed Clinton ahead were cooked, he said. Early votes in favor of Trump were being destroyed. Voters in Amarillo are saying their votes are being changed,” Schilling claimed during the show’s first week. “Just another day in America, boys. Gosh dang.”

If Clinton were to win, he warned there could be “an IRS retaliation, an FBI retaliation” against conservative media. “You’re talking about Russia. Soviet-era KGB type stuff. I don’t think we’re that far from it.”

Democratic immigration policies, he insisted, were an underhanded way to collapse the health care system in order to institute a full government takeover of the industry. He railed against “open borders.” At one point, he suggested a Clinton presidency could lead to an American apocalypse.

“I’m not an Armageddon guy,” Schilling said. “But I don’t think this country can survive on this trajectory for four more years. And she’s going to be worse.”

The Black Lives Matter movement was “founded on a complete lie” perpetrated by the media, he said. If the KKK is racist, he said, so is Black Lives Matter.

“I’m tired of being made to feel bad about the history of my country,” Schilling told one caller. “I am being made to feel wrong when I stand for the Pledge of Allegiance or put my hand over my heart for the national anthem,” he blared. “I don’t care what you think.”

Listen to the show, and it’s as if Schilling is back on the mound again, and the criticism he receives for his increasingly outlandish opinions is no different than the boos that once rained down on him in Yankee Stadium. They’re all proof that he’s right. “Yankee fans,” Schilling reminds his listeners now and again, “never booed a player who sucked.”

Schilling's former teammates nicknamed him "Top Step Schill" for his ability to find the cameras even when he wasn't pitching.
Schilling's former teammates nicknamed him "Top Step Schill" for his ability to find the cameras even when he wasn't pitching.
Jim Davis/The Boston Globe via Getty Images

Since October, when Schilling first told a Boston radio host that he planned to run for Warren’s seat, I’ve immersed myself in Schilling’s world – listened to his radio show, dug through his Twitter feed and blog posts, read old news clippings, and called former associates and Massachusetts political observers. Nearly everyone I spoke to agreed that Schilling’s extreme approach to politics had almost erased the joyous memories of his triumph in October 2004 and all but killed his Hall of Fame chances. It was ridiculous to think he could win a Senate race in Massachusetts, they said.

“Curt’s not running,” one state GOP official told me bluntly this past winter. Schilling “doesn’t fit the mold of the kind of Republican that historically can be competitive here,” said Matthew Baron, a longtime Massachusetts political consultant. “If this were Alabama, maybe he’d have a shot,” said Dan Payne, a Democratic consultant. “But not in Massachusetts.”

The polls and pundits both say Schilling doesn’t have a chance against Warren. They said that about Trump, as Schilling would surely remind you. But Schilling is less skilled as a provocateur than Trump. No matter your political views, his radio show isn’t any good. He’d proved himself a compelling contributor when he analyzed baseball at ESPN and called in to other people’s programs. He’s less capable when it comes to carrying a broadcast, so his show lacks the raw entertainment value of, say, a Rush Limbaugh or Glenn Beck production. He just sounds like what he is: a bitter man with a microphone.

Schilling refused multiple interview requests made through Breitbart and his lawyer, who told me that the pitcher had “no interest” in talking. So in late February, I went to the Conservative Political Action Conference just outside the nation’s capital to make one last effort.

CPAC is an annual gathering of conservative luminaries, lawmakers, media pundits and prospective politicians, a place where stars are born. There Schilling hardly fit the mold of a future candidate. He hunkered behind his microphone at Breitbart’s booth on radio row in a black button-down shirt, baggy jeans and leather flip-flops. At times, he drew the attention (and even admiration) of some bright lights of the right ― people like radio host Mark Levin, Milwaukee County sheriff David Clarke and Trump deputy assistant Sebastian Gorka. But most people barely seemed to notice his presence.

On the second afternoon of CPAC, Schilling stepped from behind radio row to mingle in the crowd, and I caught up with him for a brief moment. At first he was cordial. But when he realized I was a reporter, he took off through the crowd, the slap of his flip-flops audible for a few steps before he disappeared.

The next day, back at the Breitbart booth, he decided he would entertain my central question. How had he gone from a standard-issue Republican to a conspiracy-mongering Breitbart host? How had a man to whom the world had given so much become so … angry?

“It’s a natural progression,” he said.

Then he turned and walked away.

CORRECTION: GOP presidential nominee Mitt Romney was a wealthy venture capitalist, but he was not a billionaire.

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