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Pinstripe Alley Top 100 Yankees: #45 Roger Clemens

One of the greatest pitchers of all-time had a pretty nice tenure in pinstripes, too.

BBO-ALL STAR-CLEMENS Photo credit should read DAN LEVINE/AFP via Getty Images

Name: William Roger Clemens
Position: Starting pitcher
Born: August 4, 1962 (Dayton, OH)
Yankee Years: 1999-2003, 2007
Primary number: 22
Yankee statistics: 83-42, 4.01 ERA, 3.80 FIP, 174 GS, 1,103 IP, 1,014 K, 3 CG, 2 SHO, 88 ERA-, 83 FIP-, 21.2 rWAR, 22.8 fWAR


“Roger Clemens was a John Wayne type, an all-time hard worker... He intermixed so well with the clubhouse guys, with the lowest players on the roster... He always did more than he had to do.”
- Brian Cashman (Pinstripe Empire)

That was Roger Clemens in a nutshell. He had an insatiable drive to be the best, and there’s a strong argument that he was the best. The conversation for baseball’s greatest pitcher has to include Clemens among the mound’s elite, with a statistical resume that stacks up to Greg Maddux, Walter Johnson, Satchel Paige, and whoever else comes to mind.

Clemens was a larger-than-life figure, and he certainly had his problems as well. At the end of the day though, the Yankees employed the man with more Cy Young Awards than anyone else in history for six seasons, all of which saw them make the playoffs. He was a two-time World Series champion and the leader of their pitching staff in the most emotional postseason they ever played. It didn’t come easy.

Not Yet A Rocket

Clemens established his identity as a Texan through and through, but the truth is that most of his youth wasn’t even spent in the Lone Star State. He was born William Roger Clemens in Dayton, Ohio on August 4, 1962, the son of Bess Clemens and her husband, Bill. Roger wanted nothing to do with his namesake, as Bess left her husband when Roger was just five months old. A Navy veteran from World War II and seven years her senior, his long road trips as a truck driver for a chemical plant put a strain on their marriage. Bill and Roger spoke only once in their lives, when Roger told him off at age 10 for bothering Bess. His father died in 1981.

Bess Clemens remarried a couple years later to an older mechanic named Woody Booher, who got her pregnant. To his credit, Booher heartily embraced Clemens and his family, and Roger had some nice years for awhile outside Dayton. Then at age eight, Clemens lost a second father when Booher suffered a heart attack.

Roger found a bit of an unlikely father figure in his older brother, Randy. He was only nine years older, but he was his brother’s idol. A star athlete for his high school and the classic “big man on campus,” Roger desperately wanted to be like Randy. The brothers loved each other dearly, and five years after their step-father’s passing, Randy offered to take some of the load off his mother and grandmother’s responsibilities by moving Roger down to live with him and his new wife in Houston in the middle of high school.

Back then, Roger was socially awkward, quite unathletic, did not throw hard at all, and he was far from the person he’d later become. He readily accepted this new life in Houston and set about becoming a much better baseball player. Randy was a tough man to please, but Roger developed a remarkable work ethic under his brother’s guidance. Furthermore, he became comfortable at school, as his sister-in-law Kathy helped him with schoolwork and eroding some of that awkwardness. He spent one year at Dulles High School before moving on to a much better program at Spring Woods under coach Charlie Maiorana.

Clemens had a fierce motivation to became a big-leaguer, but by the end of high school, he was still only hovering in the eighties on his fastball without much life on his breaking pitches. Maiorana liked him a lot though, so he called in a few favors and got a scholarship for the undrafted 17-year-old at a junior college, San Jacinto State. Clemens took the offer, and he bloomed under coach Wayne Graham.

Graham was the man to finally unlock Clemens’ athletic potential, as he encouraged him to “finish hard” on his pitches; Clemens had been taught otherwise by his brother. Before long, the velocity started to tick up to the nineties and he turned into the ace on a conference championship team. Pro teams noticed, and the Mets selected him in the 12th round of the 1981 draft.

Clemens turned the Mets down though, as an opportunity had come up to realize his dream—pitching at the University of Texas. It also involved quickly burning bridges with Graham and San Jacinto, but he did it. The gamble paid off, as he became one of coach Cliff Gustafson’s best weapons on the pitching staff.

Clemens had a 1.99 ERA in his first year at Texas, and they made it to the semifinals of the College World Series. They took it one step beyond in 1983, winning the title over Alabama with Clemens tossing a complete game victory.

The right-hander was ecstatic to be a winner, but he was already looking forward to his next challenge. Five days prior, the Boston Red Sox had announced that they were taking Clemens with the 19th overall pick in the draft. Before long, his previously far-fetched dream of being a big-leaguer would be realized.


Clemens did not waste much time in the minor leagues. He was untouchable from the get-go, recording a 1.33 ERA in 11 starts between High-A Winter Haven and Double-A New Britain in ‘83, fanning 95 batters in 81 innings while leading New Britain to the Eastern League championship. In his fourth professional start, he threw a 15-strikeout shutout ... and almost sparked a brawl by drilling an opposing player for sliding hard into second base a couple days prior. That set the tone for his MLB career, as Clemens was always the type of pitcher who was determined to intimidate.

Despite a shaky spring training, the Red Sox began Clemens’ 1984 season a step away from the pros with Triple-A Pawtucket. He twirled a 1.93 ERA in 46.2 innings, completing half his starts. There was no point in forcing Clemens to trifle with minor leaguers. He was ready for The Show, and he made his MLB debut on May 15th in Cleveland.

Sports Contributor Archive 2020 Photo by Ron Vesely/Getty Images

Clemens quickly discovered that the major leagues were a helluva lot more difficult than the minors though, and he struggled in his first two months with a 5.94 ERA and .836 OPS against in 12 starts. He was even briefly removed from the rotation and pitched out of the bullpen in mid-July.

Given another chance in the rotation by veteran skipper (and former Yankee) Ralph Houk, Clemens rewarded his faith with a four-hit shutout on July 26th, striking out 11 White Sox. He completed half of his final eight starts, recorded a 2.63 ERA over the stretch, and fanned 15 Royals in a gem on August 26th. He was shut down for the year with a forearm strain in September, but his impressive finish was enough to garner some down-ballot Rookie of the Year votes.

After an injury-plagued sophomore season in 1985, Clemens underwent arthroscopic surgery on a torn labrum in his shoulder. It wasn’t a major tear though, so he did not have to miss any time in ‘86. His physical therapy to strengthen his shoulder turned out to be a blessing in disguise, as he was completely prepared for stardom. Clemens won all of his first three starts and announced his presence to the rest of the majors on April 29th, one of the best starts in MLB history:

At the mere age of 23, Clemens broke the previous MLB record of 19 strikeouts in a game by fanning 20 Mariners. It was an eye-popping total, but he was just getting started. The Red Sox won the AL East for the first time in 11 years as Clemens became a superstar with a 24-4 record, 238 strikeouts in 254 innings, 8.8 rWAR, and league-leading marks of a 2.48 ERA (57 ERA-), 2.81 FIP (69 FIP-), and a 0.97 WHIP. He was named the All-Star Game starter in his adopted hometown of Houston, won the All-Star MVP with three scoreless innings, and took home more honors at season’s end with the Cy Young Award and the AL MVP.

It was a breathtaking season that saw the Red Sox fight back from their last strike down 3-1 in the ALCS to beat the Angels, only to fall in heartbreaking fashion to the Mets in the World Series after getting them down to their last strike. The Curse of the Bambino was alive.

Clemens was not overwhelming in the postseason, partially due to fatigue and a line drive off the elbow in his last regular-season start, and he and manager John McNamara have differing accounts about whether he asked out of the potential championship clincher in the eighth inning of Game 6 with a blister. (For what it’s worth, given the crazy competitor that Clemens was, I doubt that.) Regardless, Clemens never got that close to a title again in Boston.

The remainder of Clemens’ tenure with Boston was a combination of incomparable excellence on the mound and controversy. He did not have a good relationship with the media, he had contract disputes with management (even walking out of spring training in ‘87), he was stunningly ejected at the start of Game 4 of the 1990 ALCS (Boston was swept by the A’s), and he was arrested at a nightclub in January 1991 for trying to stop an off-duty police office from arresting his brother Randy, who was battling drug problems.

It was also around this time when, unbeknownst to the public, he began an affair with country singer Mindy McCready, who was only 16. Clemens denied it and McCready said the relationship only became sexual “several years later,” but the real story is unclear. McCready tragically took her own life in 2013 after legal issues and several previous attempts.

Yet throughout it all, Clemens remained a tremendous player on the mound. He took home the ‘87 and ‘91 Cy Young Awards, made four more All-Star teams, and led the league multiple times in ERA, complete games, shutouts, strikeouts, FIP, and WAR. He would occasionally put up simply startling marks, like 18 complete games in ‘87, eight shutouts in ‘88, and 10.4 rWAR in ‘90, when he was robbed of a Cy Young by 27-game winner Bob Welch (worth just 2.9 rWAR with a much higher ERA). Clemens was menacing with his tendency to throw inside, but he was also meticulous, constantly changing signs with complex signals for his catcher. Clearly, it worked.


The Red Sox won three more AL East crowns with Clemens, in ‘88, ‘90, and ‘95, but they were swept in the first round each time. Management grew tired of dealing with Clemens, and they decided that it was time to move on after ‘96. Although he led the AL in strikeouts with 257 and tied his own record with 20 strikeouts on September 18th in Detroit, he was 40-39 with a 3.77 ERA since the start of ‘93. His numbers made him the best starter in Red Sox history and even recently, he was terrific in other categories. In the rudimentary days of baseball analytics though, Boston thought he was nearing the end at age 33.

GM Dan Duquette infamously said that Clemens was “in the twilight of his career” and didn’t make much of an offer in free agency. Incensed, Clemens bolted for the division rival Blue Jays on a three-year, $24.75 million deal.

The Rocket instantly bounced back to whatever glory might have faded by making his first All-Star team in five seasons, and leading the AL in wins (21), ERA (2.05), complete games (9), innings (264), strikeouts (a career-high 292), FIP (2.25), WHIP (1.03), and WAR (a career-high 11.9). He was the easy pick for the Cy Young Award, and perhaps most satisfyingly, he annihilated the Red Sox with 16 K’s in his return to Fenway Park on July 12th:

In 1998, Clemens was back at it again with more success and eventually, a unanimous Cy Young Award, his fifth. That broke the record of four set by Steve Carlton and Greg Maddux. It was that year though that the Blue Jays hired Brian McNamee as their strength and conditioning coach. With a tip from teammate Jose Canseco, Clemens began using the steroid Winstrol that year, according to McNamee’s testimony in the 2007 Mitchell Report. He later expanded to using human growth hormone, and McNamee served a similar role with the Yankees. Clemens has always denied it and was able to get all suits against him dismissed, but the accusations are there.

By the outset of the ‘99 campaign, Clemens was nearing his 37th birthday and wanted to pitch on baseball’s biggest stage again. The Blue Jays simply weren’t going to be good enough to usurp the Yankees, who had just won 114 games and secured their second championship in three years. George Steinbrenner loved characters like Clemens though, even on the heels of him inciting a Yankees/Blue Jays brawl at the end of ‘98.

The cost to get Clemens was not light either, but ultimately, GM Brian Cashman pulled the trigger, dealing popular ace David Wells, reliever Graeme Lloyd, and infielder Homer Bush to Toronto for the two-time defending Cy Young Award winner on February 18, 1999, the first day of spring training.

The Boss got his wish: Roger Clemens was a Yankee.


The Yankees clubhouse was not entirely thrilled at the prospect of adding this headhunter to the team, but they decided to make do. On Clemens’ first day in Yankees camp, Derek Jeter and Chuck Knoblauch eased the tension by donning full catcher’s gear in batting practice against him. Before long, the team came to love his competitive spirit and admire his absolute determination to stay in shape and keep his legs strong despite his age.

Fans also grew more familiar with Clemens’ odd tradition of rubbing sweat on Babe Ruth’s monument for good luck before each start.

The first season in New York was somewhat rocky for Clemens. He looked nothing like the fierce opponent who won consecutive Cys, and as late as July 19th, he had an ERA of 4.98 — unsightly for even the height of this era of high-octane offense. Clemens turned it around a little bit afterward with a 4.23 ERA and .709 OPS against the rest of the way — perhaps due to a little luck from changing his number from 12, which he wore at first with the Yankees, to 22, his son Koby’s favorite number.

The Yankees won the AL East and Clemens spun a fine performance in his first playoff start in four years, shutting out the powerful Rangers over seven innings in the clinching ALDS Game 3. During the Championship Series in Boston, he was public enemy number one at Fenway, and Game 3 of that series was billed as “Old Ace vs. New Ace” since Clemens was taking on Pedro Martinez. He was routed, 13-1, the Yankees’ only loss of that postseason. Undeterred, the Rocket was dominant again in Game 4 of the World Series against the Braves, spinning 7.2 innings of one-run ball before turning it over to Mariano Rivera.

The nonpareil closer finished off the sweep, and Clemens at last had his first World Series ring.

The 2000 season was superior on the field for Clemens, but it was painful away from it. By then, his brother Randy’s marriage to his wife Kathy had long since fallen apart due to his drug problems, and their son fell victim to the habit as well. On May 17th, Kathy Clemens was shot to death by a group of five young men who came to her house to confront her son about money owed for drugs. The murder deeply wounded Roger, for he considered Kathy to be a second mother from her time spent raising him as an awkward teen. He quietly settled Kathy’s funeral expenses and completely cut Randy out from his life, since he blamed him for both his nephew’s descent into drugs and Kathy’s murder. It was a startling fall from the grace for the man Clemens once considered a hero.

Clemens pitched through the emotional pain to notch a 4.6 rWAR season and some down-ballot Cy Young votes. Although they suffered a miserable September slide, the Yankees captured the AL East with just 87 wins. Clemens was terrible in the Division Series against the upstart A’s, who pounded him twice for losses. The Yankees powered through anyway, and Clemens had a chance to redeem himself in Game 4 of the ALCS, facing Seattle. He delivered with one of the best starts in postseason history:

Only a double by Al Martin barely off Tino Martinez’s glove kept Clemens from a no-hitter as he fanned 15 in a brilliant shutout. He brushed back Alex Rodriguez multiple times, his splitter was in rare form, and he was simply unbelievable. Before long, the Yankees dispatched the Mariners for the pennant.

Clemens was also superb in his lone World Series start against the Mets, in which he threw eight shutout innings of two-hit ball. The Yankees went on to win their third straight championship in five games. That wasn’t the story though. Instead, coverage centered around his rivalry with Mike Piazza. The future Hall of Famer had absolutely pounded Clemens with seven hits and three homers in just 12 at-bats, including a booming grand slam on June 9th of that year. Clemens retaliated by beaning him a month later, an injury that later led to a concussion, forcing Piazza to miss time and the All-Star Game. So there was already bad blood.

World Series Game 2 featured the first at-bat between them since then. Piazza hit a broken-bat foul ball, and half the bat bounced toward Clemens, who inexplicably chucked it at Piazza, half-running up the first-base line. Piazza was furious, the benches cleared, and everyone at Yankee Stadium was left wondering why the hell Clemens chucked a broken bat at Piazza. He later claimed that he thought it was the ball, which seems like a laughable excuse. The Mets got their revenge in 2002, the next time Clemens faced them in interleague play at Shea Stadium. Opposing pitcher Shawn Estes failed to plunk Clemens (he missed and threw behind him), but he stunningly took Clemens deep. The rivalry reached an amusing coda when Clemens had to later pitch with Piazza at catcher in the 2004 All-Star Game.

2001 was a huge year for Clemens, who broke Walter Johnson’s longtime AL strikeout record in April and went on to capture baseball’s attention that year by starting the season 20-1. Sure, it was partly a product of playing for a good team that could help him get the wins, but it had never been done before in MLB history (it wasn’t as though he was pitching poorly either). That feat alone was enough to return him to the Midsummer Classic and win his sixth Cy Young Award, though new teammate Mike Mussina had a better case beyond wins in basically every category. He was the last Yankee to take home the Cy Young until Gerrit Cole this past season.

Clemens battled a hamstring injury throughout the playoffs as the Yankees sought their fourth straight championship and a minor respite for New York City in the wake of 9/11. The A’s roughed him up again in the Division Series, but he took care of business against the 116-win Mariners in the ALCS. He then threw seven excellent innings in World Series Game 3 against Arizona to help the Yankees avoid an 0-3 deficit. Clemens followed that up by dueling Curt Schilling to a stand-still in Game 7, striking out 10 batters over 6.1 innings of one-run ball, though sadly it was to no avail.

To Retire or Not to Retire?

As he turned 40 in 2002, Clemens began to debate the end of his career. He finally seemed to be slowing down, as he missed some time due to injury and saw his numbers slide back to his so-so ‘99 form. The Yankees romped to another division title, but the Angels shocked the world by blitzing the four-time defending AL champions in a four-game ALDS.

So early on in 2003, Clemens announced that it would be his final season. He cited a desire to return home, and to see his beloved ailing mother survive to see him enter Cooperstown soon (Bess Clemens eventually passed away in 2005). He did seem to rise to the occasion in his “farewell year,” making another All-Star team, rebounding to 4.0 rWAR, and reaching two huge milestones on June 13th against the Cardinals: 300 wins and 4,000 strikeouts.

The Yankees and Clemens made it to another World Series in 2003, albeit not before an infamous ALCS bench-clearing incident at Fenway Park that naturally involved Clemens and Pedro. In Game 4 of the Fall Classic, he received an ovation in Miami after leaving his final start, seven innings of three-run ball. The Marlins ended up stunning the Yankees in a six-game victory, apparently ending a Hall of Fame-bound career.

Then in the offseason, the Yankees oddly allowed Clemens’s close friend Andy Pettitte to walk in free agency without much of an effort. He signed with the Houston Astros, and since they were so close to home, Clemens began to feel the desire to pitch again. With his family’s encouragement, he came out of his oh-so-brief retirement to sign with the Astros as well. In the National League for the first time, Clemens had much more left in the tank than he realized. He went 18-4 with a 2.98 ERA, 3.11 FIP, and 5.4 rWAR, winning his seventh Cy Young Award.

While Clemens and the Astros fell short in Game 7 of a dramatic NLCS rumble with the Cards, they both came back with a vengeance in 2005. At age 42, Clemens posted 7.8 WAR and had a career-best 1.87 ERA (44 ERA-) in 211 innings, making his 11th and final All-Star team. He also turned hero in the Division Series with a three-inning relief outing on short rest, as Houston needed 18 innings to dispatch the Braves in the Game 4 clincher. It was his first bullpen effort since his brief midseason demotion as a rookie 21 years prior.

Clemens won his NLCS Game 3 start, and this time the Astros beat the Cardinals for their first pennant, despite the best efforts of Albert Pujols. Unfortunately, Clemens had to depart his real final Fall Classic start against the White Sox in ignominious fashion, just two innings into Game 1 due to injury. The Astros were swept.

Once again, Clemens went back and forth on whether to retire or not, sitting out spring training of 2006 before ultimately returning to the Astros in June with permission to stay with his family on select road trips. He passed his 44th birthday still sharp with a 2.30 ERA and 1.04 WHIP in 19 starts, but Houston missed the playoffs.

For a second-straight year, Clemens went through the song and dance of deciding whether or not to pitch. This time, it was the Yankees who pulled him out of retirement. They had badly struggled in April and were decimated by pitching injuries, so Steinbrenner pulled some strings and Cashman got Clemens to agree to a pro-rated $28 million contract for one year, with the same unusual road trip permissions as his previous Houston deal. To say that radio announcer Suzyn Waldman was excited when Clemens announced his return mid-game is an understatement.

Clemens rejoined his old friend Pettitte in the Yankees rotation, as the southpaw had re-signed with them in the offseason. This time, a 45-year-old Clemens finally ran out of gas; he could only manage middling numbers in 99 innings (17 starts). Considering his age, a 4.18 ERA wasn’t shabby at all and he notched his 350th career victory on July 2nd against the Twins, but it paled in comparison to his Astros years.

The Yankees did rally to reach the playoffs as the Wild Card, but like his final World Series appearance, Clemens’ final playoff start was an injury-ravaged wash. He left in the third inning and needed to be bailed out by rookie Phil Hughes for the Yankees to avoid a sweep. They lost the series to Cleveland the next day.

Even if Clemens wanted to return once more in 2008, the Mitchell Report released in November ‘07 nixed any of those hopes. His dirty history of likely PED use was revealed to the world by his old trainer McNamee, despite the pitcher’s denials. His affair with McCready came out then too, which didn’t help matters. His friendship with Pettitte also seemed to fall apart when the lefty testified against him. The Yankees have barely acknowledged his presence on the dynasty teams since then, and returns to Yankee Stadium have been few and far between. Clemens fought with whatever legal strength he could manage and did get them dismissed, but the PR damage was done.

While Clemens ranks among the best pitchers in baseball history, the PED connection dogged him as much as Barry Bonds in BBWAA voting for the Hall of Fame. The pair left baseball the same year and debuted on the 2013 ballot with little over a third of the vote. The closest Clemens got to enshrinement from that bloc was when he earned 65.2 percent during his final year of eligibility, 2022.

Bonds fell off the ballot that year too, and though he and Clemens got a look before the modern Veterans Committee (the “Eras Committee”) during the next cycle, they didn’t even come close. As Hall of Fame expert Jay Jaffe has noted, the deck was stacked against them with how Cooperstown leadership selected the committee. As it stands today, it seems unlikely that Clemens or Bonds will ever have Hall of Fame plaques like the commissioner who presided over that controversial era, Bud Selig.

There has never been an MLB pitching career quite like the long, winding road of Roger Clemens. He was one of the most successful players to ever take the mound, and yet he’ll probably never be a Hall of Famer. He delivered dominant playoff performances (including the best one ever by Game Score) while also enduring some ugly ones as well. Tragedy and hardships beyond his control plagued his life, but he later caused more than his share of his own problems, both on and off the field.

For all the highs, lows, and everything complex in between, Clemens is an easy qualifier for the Top 100 Yankees. I have no idea what lies next in his future, but his past is something to behold.

Staff rank: 44
Community rank: 58
Stats rank: 60
2013 rank: 58

This biography has been repurposed from an original version that ran in 2017.


Appel, Marty. Pinstripe Empire: The New York Yankees from Before the Babe to After the Boss. New York: Bloomsbury, 2012.

Baseball Reference

BR Bullpen

Bush, Frederick W. SABR bio


Jaffe, Jay. “JAWS and the 2021 Hall of Fame ballot: Roger Clemens,” FanGraphs, 7 Dec. 2016.

Madden, Bill. Steinbrenner: The Last Lion of Baseball. New York: HarperCollins, 2010.

Olney, Buster. Last Night of the Yankees Dynasty. New York: Ecco, 2004.

Pearlman, Jeff. The Rocket That Fell to Earth: Roger Clemens and the Rage for Baseball Immortality. New York: HarperCollins, 2009.

Verducci, Tom and Joe Torre. The Yankee Years. New York: Doubleday, 2009.

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