MLB's Biggest 'What-If?' Moments in Recent History

Zachary D. RymerAugust 17, 2022

MLB's Biggest 'What-If?' Moments in Recent History

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    What if Grady Little had pulled Pedro Martinez in Game 7 of the 2003 American League Championship Series? (AP Photo/Charles Krupa, File)

    There's only one timeline in this reality for everything that's ever occurred in Major League Baseball, but it's hard not to think about what would be different if things that could have happened actually, you know, happened.

    In other words, who's up for a game of MLB What-Ifs?

    Ahead are our picks for the 15 most fascinating hypotheticals of the 21st century. These contain all manner of watershed-type moments, from alternative transactions and draft picks to critical in-game events that could have gone other ways. In all cases, recent MLB history would have unfolded in a dramatically different way if things had gone differently in these moments.

    Since there's no good way to rank these events, we'll proceed in chronological order.

1999/2000: What If the Mariners Had Extended Alex Rodriguez?

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    Ronald Martinez/Getty Images

    What Actually Happened?

    The writing was on the wall that Ken Griffey Jr. wasn't long for the Seattle Mariners after the conclusion of the 1999 season, and he indeed left the Pacific Northwest via a trade with the Cincinnati Reds in Feb. 2000.

    The Mariners did, however, intend to keep fellow superstar Alex Rodriguez—so much so that they offered him an eight-year contract worth over $15 million per year in Oct. 1999. Had he accepted, he would have become the highest-paid player in baseball at that time.

    Rodriguez not only declined but closed the door on negotiating until after the conclusion of the 2000 season. He subsequently notched a third straight 40-homer season and left to join the Texas Rangers on a deal worth more than twice what the Mariners had offered.


    What Might Have Happened?

    The assumption here is that Rodriguez might have been willing to negotiate during the 2000 season and that the Mariners upped their offer to something more to his liking.

    A reach? Sure. But one nonetheless worth making for the sake of imagination. With the 2001 version of A-Rod, who became only the fourth player to record 200 hits and 50 home runs in a season, that year's Mariners may not have stopped at 116 wins. Or, for that matter, at one series victory in the playoffs.

Oct. 2001: What If Jeremy Giambi Had Slid?

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    What Actually Happened?

    After winning 47 of their last 58 games in the regular season, the 2001 Oakland Athletics remained supernova with back-to-back wins to open the American League Division Series against the New York Yankees.

    In a Game 3 matchup between aces Mike Mussina and Barry Zito, the latter blinked first when he gave up a solo home run to Jorge Posada in the fifth. It wasn't until the seventh that the Yankees' lead came under threat when Terrence Long hit a two-out double down the right field line that had a chance to score Jeremy Giambi from first base.

    Out of nowhere, though, came Derek Jeter to flip the relay throw to Posada at home plate. Giambi tried to go in standing but was tagged out. From there, the Yankees won the game 1-0 and went on to complete the comeback in Games 4 and 5.


    What Might Have Happened?

    Would Giambi have been safe if he had gone into a slide? Posada, the very man who tagged him out, put it this way in 2021: "If he slides, he's safe. For sure. 100 percent. 100 percent."

    If so, the score would have been knotted 1-1, and the A's would have had a runner in scoring position. Had that situation led to an A's win, they would have faced the 116-win Mariners in the ALCS and completely rewritten the opening to Moneyball.

Nov. 2001: What If the Yankees Hadn't Choked?

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    What Actually Happened?

    When the '01 Yankees later met the Arizona Diamondbacks in the World Series, a classic of epic proportions culminated in the former clinging to a 2-1 lead in the bottom of the ninth inning of Game 7.

    All the Yankees needed was three outs from Mariano Rivera. But no thanks to an error of his own and a mental gaffe on the part of Scott Brosius, Rivera got just one out before giving the lead away on a run-scoring double by Tony Womack.

    When Luis Gonzalez strode to the plate with the bases loaded, Fox broadcaster Tim McCarver warned that the Yankees were risking a broken-bat hit by playing the infield in. As if on cue, Gonzalez floated Rivera's next cutter into the outfield to end the series.


    What Might Have Happened?

    By making Rivera work and taking the extra outs that the Yankees provided, the Diamondbacks did what they had to in order to pull off the comeback. So, no disrespect to them.

    But if two things can be true at once, then the Yankees lost the game as much as the Diamondbacks won it. And in doing so, they missed out on a chance to join the Yankees from 1936-39 and 1949-53 as the only teams to ever win four World Series championships in a row.

Oct. 2003: What If the Cubs Hadn't Given Up That 3-0 Lead?

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    What Actually Happened?

    With the Chicago Cubs on one side and the Florida Marlins on the other, the 2003 National League Championship Series featured one team that was 95 years removed from its last World Series title and another team that was only in its 10th year of existence.

    Far from any kind of mismatch, the series played out as a compelling back-and-forth until the Cubs seemed to take control in Game 6 at Wrigley Field. When Mark Prior took the mound for the eighth inning with a 3-0 lead, the Cubs had a 93 percent chance of winning the game and the series.

    A short while later, however, Chicago's lead turned into an 8-3 deficit in front of a stunned crowd. There was that one incident involving a fan, but he guy didn't leave a tiring Prior in to throw 119 pitches or boot what could have been an inning-ending double play ball. That was all on the Cubs, as was their subsequent 9-6 loss in Game 7.


    What Might Have Happened?

    If nothing else, the aforementioned fan wouldn't have become an undeserving scapegoat for a veritable army of Cubs fans if that 3-0 lead had held up.

    More directly, a win would have put the Cubs in their first World Series since 1945. With better luck and cleaner play, they might not have had to wait another 13 years to finally snap their championship drought.

Oct. 2003: What If Grady Little Had Pulled Pedro Martínez?

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    What Actually Happened?

    Once they took a 5-2 lead into the bottom of the eighth of Game 7 of the 2003 American League Championship Series, only six outs separated the Boston Red Sox from a long-awaited triumph over their mortal enemies and a trip to their first World Series since 1986.

    Having already pitched seven strong innings, Pedro Martínez thought he was done for the night. He surely should have been after Little visited Martínez on the mound with one out, a man on first and a run already in.

    Instead, Little didn't pull his ace until after he had thrown 123 pitches and allowed back-to-back doubles by Hideki Matsui and Jorge Posada to tie the game.

    The Red Sox never really sniffed a run of their own after that, and Aaron Boone sealed their doom with a walk-off home run leading off the 11th.


    What Might Have Happened?

    If it had been Mike Timlin in the eighth and Scott Williamson in the ninth, chances are the Red Sox would have held on. The two righties had been nails for Boston in the playoffs to that point, allowing just one run over 16.1 innings.

    Then again, would the Red Sox also have lost to the Marlins in the World Series, as the Yankees did? Maybe so. Then there's the other question of how a different outcome in the 2003 ALCS would have altered the setting of the stage for what happened in 2004.

June 2006: What If the Tigers Had Drafted Clayton Kershaw?

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    Set Number: X81232 TK2 R2 F345

    What Actually Happened?

    Two years after they landed Justin Verlander with the No. 2 pick in the 2004 draft, the Detroit Tigers had a chance to score yet another generational ace with the No. 6 selection in the 2006 draft. In fact, Clayton Kershaw was convinced it would happen.

    "I thought I was going to the Tigers," he would later say in 2013. Detroit ultimately opted for a different southpaw when they took Andrew Miller out of North Carolina, leaving the Los Angeles Dodgers to nab Kershaw with the No. 7 pick.

    The rest is history. Miller went on to have a fruitful career, particularly as a reliever in the latter half of his 16 years in the majors. Kershaw, meanwhile, turned into perhaps the greatest pitcher of his era and a surefire first-ballot Hall of Famer.


    What Might Have Happened?

    If the Tigers had chosen Kershaw, they could have eventually fielded a rotation with him, Verlander, Max Scherzer and Rick Porcello. With a foursome like that working for them in the late 2000s and early 2010s, the Tigers' World Series championship drought might not turn 38 years old after this season.

    Unless, of course, it would have been Kershaw going to Miami for Miguel Cabrera in 2007 instead of Miller. That would have changed things, and maybe more so for the Marlins than for the Tigers.

Oct. 2006: What If Carlos Beltran Had Swung?

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    What Actually Happened?

    The New York Mets and St. Louis Cardinals played an absolute classic in Game 7 of the 2006 National League Championship Series. After both teams traded early runs, it wasn't until a young Yadier Molina hit a two-run homer in the ninth that anyone led again.

    The Mets immediately put together a threat in the bottom half, putting two runners on with nobody out against Adam Wainwright. He got the next two hitters, but then walked Paul Lo Duca to bring up Carlos Beltrán with the bases loaded.

    With a 1.323 OPS and 11 home runs on his playoff resume going into that game, Beltrán was the toughest possible assignment. But Wainwright made quick work of him, getting him in an 0-2 count and then freezing him on a curveball for strike three.


    What Might Have Happened?

    As George Vecsey argued in the New York Times in 2011, Beltrán standing there frozen with his bat on his shoulders was the defining image of his time with the Mets: "Even if he had taken one last lusty 'Casey at the Bat' swing, and missed, perhaps his fate would have been different. But he gawked."

    Fair? Perhaps not. But there's no ignoring the possibility that if Beltrán had swung away, the Mets might have found themselves in the World Series with a chance to snap a championship drought that, in 2022, is now 36 years old.

Oct. 2007: What If Matt Holliday Had Been Called out?

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    Doug Pensinger/Getty Images

    What Actually Happened?

    On Sept. 15, 2007, the San Diego Padres led the Colorado Rockies by 4.5 games in the race for the National League's wild-card spot. But then the Padres finished 9-6 while the Rockies ripped off 13 wins in 14 games, setting up a Game 163 tiebreaker at Coors Field.

    With the score knotted up at 6-6 in the top of the 10th, Scott Hairston hit a two-run homer to put San Diego ahead. But the Rockies tied the game again in the bottom half with knocks from Troy Tulowitzki and Matt Holliday.

    With Holliday on third and nobody out, Jamey Carroll lofted a line drive to right field that was deep enough for Holliday to test Brian Giles' arm. It wasn't clear on replay whether he touched the plate on his slide. But sans a clean catch by Michael Barrett, umpire Tim McClelland called Holliday safe to end the game.


    What Might Have Happened?

    Though everyone watching from home had the benefit of watching Holliday's slide over and over in slow-motion, these were the days before umpiring crews were privy to reviews. All McClelland could do was trust his eyes.

    As it only would have been the first out of the inning, the Rockies still would have stood a good chance of winning even if Holliday had been called out. But had the Friars escaped the jam, maybe they would have been the ones to ultimately end up in the '07 World Series.

Dec. 2007: What If the Angels Had Traded for Miguel Cabrera?

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    Elsa/Getty Images

    What Actually Happened?

    Before the Tigers ultimately swooped in and grabbed him in a deal that notably did not include Kershaw, the Los Angeles Angels were the front-runner to land Cabrera from the Marlins during the 2007-08 offseason.

    Reports at the time claimed that the Angels and Marlins agreed that Howie Kendrick and Jeff Mathis would be part of the deal but were having trouble coming to terms on which pitcher would also go to Miami. Among the possibilities were Ervin Santana and Joe Saunders.

    Though talks eventually fell through, they were apparently serious enough that Cabrera was readying himself to go to Anaheim. As he later said while visiting with the Tigers in 2013: "I thought I would be here."


    What Might Have Happened?

    Had the Angels traded for Cabrera, the immediate benefit would have been to teams that went to the playoffs in 2008 and 2009 despite the lack of power in their lineup. The Angels tied for eighth among AL clubs in home runs across those two seasons.

    If the Angels had likewise circumvented Cabrera's free agency with an extension, they wouldn't have had to sign Albert Pujols after 2011. And come 2012, Cabrera would have been paired with the very guy he battled in the AL MVP races of 2012 and 2013: Mike Trout.

Oct. 2011: What If That David Freese Fly Ball Had Found Leather?

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    What Actually Happened?

    Early on, Game 6 of the 2011 World Series between the Cardinals and Texas Rangers was one of the sloppiest World Series games ever played. Slowly but surely, though, it turned into a classic.

    All dramatic roads led to Neftalí Feliz on the hill to protect the Rangers' 7-5 lead in the bottom of the ninth.

    But with two outs, two on and two strikes, David Freese hacked at a 98 mph fastball from Feliz and sent it just over the reach of Nelson Cruz in right field to tie the game. Freese eventually played the hero again with a walk-off home run in the 11th inning.


    What Might Have Happened?

    After the Rangers' crushing loss in Game 6, one of the questions in the air was why Cruz wasn't playing deeper. Even Cruz himself acknowledged that he would have changed his positioning if he could have a do-over.

    The other question was whether Cruz should have even been out there, as manager Ron Washington could have used noted playoff home run thief Endy Chávez as a defensive replacement rather than as a pinch-hitter in the top of the ninth. Either way, Freese's ball is one that conceivably should have been caught.

    Instead of erasing their World Series disappointment from the year before and capturing the franchise's first-ever championship, the Rangers fell short for the second consecutive year.

Sept. 2012: What If the Nationals Hadn't Shut Stephen Strasburg Down?

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    AP Photo/David Tulis

    What Actually Happened?

    Stephen Strasburg never was destined to pitch many innings for the Washington Nationals in 2012. In the wake of Strasburg's Tommy John surgery in 2010, Nats general manager Mike Rizzo knew even in 2011 that the right-hander would be on an innings limit in 2012.

    Though Strasburg pitched brilliantly through his first 27 outings of 2012, he gave the Nats the excuse they needed with a bomb in his 28th start. They shut him down, simultaneously protecting his future and denying the eventual 98-win team the presence of a dangerous weapon for the playoffs.

    It backfired. Though the Nats were done in by a bullpen collapse opposite the Cardinals in Game 5 of the National League Division Series, also to blame for the defeat was a Strasburg-less starting rotation that posted a 5.25 ERA.


    What Might Have Happened?

    Would the Nationals have beaten the Cardinals if they'd had Strasburg in the 2012 NLDS? Perhaps if the full-strength version of him had shown up, but it's hard to take that for granted. Even despite the shutdown, the 159.1 innings he pitched that year were by far a career high.

    What's for sure is that the shutdown didn't derail Strasburg's career. He mostly flourished in the seven seasons that followed, and never more so than during Washington's dramatic World Series run in 2019. Had he racked up more innings in 2012, there's a non-zero chance that he would have burned out before then.

Oct. 2014: What If the Royals Had Sent Alex Gordon?

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    What Actually Happened?

    As had been the case in Games 1 and 5, the Kansas City Royals didn't have an answer for Giants ace Madison Bumgarner after he entered in relief in the fifth inning of Game 7 of the 2014 World Series. By the time there were two outs in the ninth inning, he had allowed just one hit.

    Then all Heck broke loose. Alex Gordon lofted what initially looked like a single to center field, but he was able to hit the gas after the ball skipped past Gregor Blanco and rolled all the way to the wall. At third base coach Mike Jirschele's behest, Gordon stopped at third.

    It was thus up to Salvador Pérez to try to make it two hits in a row against Bumgarner, but he popped out to Pablo Sandoval in foul territory to end the series.


    What Might Have Happened?

    As for whether Gordon should have been sent, Matthew Leach of MLB.com ran the numbers and found them to be favorable to Jirschele's stop sign—and yet, not so much that there was zero chance of him and the Royals being rewarded if he'd forced the Giants to make a play.

    Had Gordon scored in the face of the odds, the Royals would have been in a tie game at home. Had they come through with a win and still gone on to win the 2015 World Series as well, they'd have become MLB's first back-to-back champions since the 1998-2000 Yankees.

Oct. 2016: What If That Rain Delay Hadn't Happened?

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    Jamie Squire/Getty Images

    What Actually Happened?

    With their 3-1 series advantage having evaporated, things were looking bleak for the Cleveland soon-to-be-Guardians by the time the Cubs opened the eighth inning of Game 7 with a 6-3 lead. Miraculously, then came Rajai Davis and an earth-shaking homer that leveled the score.

    But just when regulation was ready to give way to extra innings, rain started falling on Progressive Field. The delay lasted 17 minutes, during which Jason Heyward riled up the Cubs with a fiery speech while the Guardians simply waited it out.

    Heyward's speech worked, as the Cubs would push two runs across in the top of the 10th. Seeming just about spent, Cleveland managed just one run in the bottom half to blow its shot at the franchise's first championship since 1948.


    What Might Have Happened?

    The win expectancy for Game 7 of the '16 World Series was literally 50-50 when the ninth inning ended, so perhaps it's a reach to say that conditions favored the Guardians coming out of the rain delay.

    As they were nonetheless the home team, it only would have taken one run to win it if they had been able to hold the Cubs scoreless in the top of the 10th. If they had a Heyward of their own in the clubhouse, perhaps just that would have happened.

Sept. 2019: What If That Foul Ball Had Missed Christian Yelich's Knee?

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    Mark Brown/Getty Images

    What Actually Happened?

    After winning the National League MVP in 2018, Christian Yelich was on his way to winning another for the Milwaukee Brewers in 2019. Through 129 games, he was batting .330/.430/.672 with 44 home runs and 30 stolen bases.

    Then, disaster struck in his 130th game. During an at-bat against Marlins righty Elieser Hernández in the first inning, Yelich hit a foul ball that caromed off his right leg. He left the game and was later diagnosed with a fractured kneecap, ending his season.

    Though the Brewers rallied to make the playoffs anyway, they didn't last long once they got there. The Washington Nationals saw to that, dispatching Milwaukee from the NL Wild Card Game by a 4-3 final.


    What Might Have Happened?

    Yelich at least would have been able to see his thrilling race with Cody Bellinger for the 2019 NL MVP through to a proper finish. With a win, he would have become the first NL player to claim back-to-back MVPs since Pujols in 2008 and 2009.

    More importantly for the Brewers, it would have been Yelich and not Trent Grisham in right field for the NL Wild Card Game. The more experienced Yelich might not have allowed three runs to score on Juan Soto's eighth-inning single. That hit ended a pursuit for a World Series championship that's still ongoing in Milwaukee.

Oct. 2019: What If Dave Roberts Hadn't Stuck with Clayton Kershaw?

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    What Actually Happened?

    After winning 106 games in the regular season, the 2019 Dodgers began the National League Division Series as a heavy favorite over a Nationals team that might not have survived the Wild Card Game if the Brewers had still had their MVP in right field.

    Yet the Nationals played the Dodgers to a decisive Game 5, where they eventually threatened to erase a 3-1 deficit by putting a pair of runners on with two outs in the seventh. Dodgers manager Dave Roberts had to call on Kershaw to put out the fire, which he did with an inning-ending strikeout of Adam Eaton.

    But in lieu of letting someone else take over in the eighth, Roberts sent Kershaw back out. He gave up game-tying home runs to Anthony Rendon and Juan Soto, thus paving the way for Kendrick's series-winning grand slam in the 10th.


    What Might Have Happened?

    Maybe it wasn't on the same level as Little and Martínez, but Roberts' decision to stick with Kershaw was rightfully dragged afterward. Like Timlin and Williamson for Boston back in '03, Joe Kelly and Kenley Jansen were right there.

    Maybe either one of them might also have fallen victim to Washington's clutch hitting. But if not, the Dodgers would have survived and perhaps gone on to end their World Series championship drought a year early.


    Stats courtesy of Baseball Reference.

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