Red Sox History: Ranking the biggest ‘What Ifs’ in franchise history

The Red Sox have some of the biggest ‘What-Ifs’ in history

It’s hard to feel too bad for Red Sox fans recently. Their team plays in the most beloved ballpark in baseball, has owners who truly care about the team and are willing to spend money, are competitive almost every year, and, oh yeah, have won four World Series titles in the last eighteen years.

Still, Red Sox history is not without its what-ifs. Whether it be a costly trade, a bad break in a critical game, or a late-season collapse. The Red Sox could have easily won a few more titles if a couple of things had gone in their favor.

When making these rankings, my one rule was to stay clear of individual players. I solely focused on team-oriented topics. So while players like Tony Conigliaro and Jimmie Foxx never reached their full potential due to injuries, they are not included on this list.

10: What if Luis Aparicio didn’t trip around third base?

The 1972 season was one of the most bizarre in baseball history, as a strike resulted in the cancelation of the first week of the season. Because of a glitch in the schedule, the Red Sox had seven games canceled while the Tigers only had six. This one game made all the difference as the two teams met in a three-game set on the seasons’ last week to decide the AL East.

Needing two out of three to win the division, the Red Sox found themselves in a quick 1-0 deficit in the first game. With two runners on in the top of the third, future Hall of Famer Carl Yastrzemski stepped to the plate.

Yastrzemski ripped what looked like a sure, two-run triple, but the speedy Luis Aparicio tripped around third base before he could score the second run. Aparicio had to retreat to third, causing Yastrzemski to scramble back to second when he was easily tagged out.

Instead of taking a 2-1 lead and having a chance for more, the Red Sox would not score again that inning. The Tigers would go on to win the game 4-1 and the division by half a game. The Red Sox had all the momentum before Aparicio’s fateful fall, a miscue that would go down as one of the costliest in team history

9: What if the Red Sox pitching didn’t collapse in September 2011

The Red Sox were sitting pretty on September 1, 2011. They had a half-game lead on the Yankees in the AL East and an 8.5 game lead on the Rays for the wild card. The offense was the best in the league, while Josh Beckett (2.54 ERA) and Jon Lester (3.09) were having Cy Young level seasons.

Yet while the offense kept up the pace in the season’s final month, averaging nearly five and a half runs a game, the pitching completely fell apart. Beckett (5.48 September ERA), Lester (5.40), and John Lackey (9.13) were terrible, and relievers Daniel Bard (10.13) and Jonathan Papelbon (two blown saves) blew the few opportunities they got. The Red Sox went 7-20 and lost the wild card to the Rays on the last day of the season.

But what would have happened if they just won one more game? The offense was still one of the best in baseball, and they had a roster stocked with postseason experience. Is it so inconceivable that they could have gone on a run in October?

And what would have happened to manager Terry Francona and Theo Epstein, both of whom resigned after the season? One more win in September could have changed the course of Red Sox history.

8: What if Bill Lee didn’t throw Tony Perez a spaceball?

It looked like the Red Sox were finally going to win the World Series. After a miraculous victory in Game 6 of the 1975 fall classic, the Red Sox took a quick 3-0 lead against the Reds in Game 7, and Bill Lee was pitching a gem. Through five innings, Lee was twirling a shutout, allowing just five hits and one walk without allowing a run.

Pete Rose singled to lead off the sixth, but Lee got Joe Morgan to fly out to right field and Johnny Bench to ground into a fielder’s choice. With the Red Sox only ten outs from a championship, future HOF’er Tony Perez came up with two down and a runner or second.

With a base open and the much less imposing George Foster on deck, Lee not only pitched to Perez, but he also threw the notorious bad-ball hitter his “spaceball,” a slow, blooping eephus pitch designed to freeze the hitter.

Perez, however, was not fooled and smacked the pitch over the Green Monster to cut the deficit to 3-2. The Red Sox had lost all the momentum, and the Reds scored singular runs in the eighth and the ninth to win the game and the series 4-3.

6: What if the Red Sox didn’t make terrible trades in the ’70s?

Three short-sighted trades by Red Sox general manager Dick O’Connell in the 1970s still sting all these years later. After the 1971 season, Red Sox management got tired of the eccentric Sparky Lyle, trading him to the rival Yankees for weak-hitting first baseman Danny Cater. Lyle would go on to make three All-Star teams, lead the league in saves twice and win the 1977 AL Cy Young, while Cater hit just 14 home runs in three forgettable seasons with the Red Sox.

Two years later, the Red Sox shipped temperamental outfielder Reggie Smith to the St. Louis Cardinals for Bernie Carbo and Rick Wise. Though Carbo had some big hits for the Red Sox, including the game-tying home run in Game 6 of the 1975 World Series, and Wise won 19 games in that pennant-winning season, neither could replace Smith. Reggie averaged more than 4.0 WAR over the next seven years, making five All-Star teams in the process.

In 1976, first baseman Cecil Cooper was traded to the Brewers for slugger George Scott, who had only one good season left in the tank after a productive career. Cooper, meanwhile, was just getting started. He made five All-Star teams, hit over .300, and led the league in doubles and RBIs twice in 11 years in Milwaukee.

For a team that came within one game of winning the World Series and finished within two games of the pennant three times in the decade, keeping these players could have made all the difference.

5: What if the Red Sox spent money at the outset of free agency?

In the mid-1970’s the Red Sox were stacked. Their lineup was filled with MVPs and future Hall of Famers Fred Lynn, Carlton Fisk, Jim Rice, and Carl Yastrzemski, while the rotation was headed by All-Stars Luis Tiant, Bill Lee, Dennis Eckersley, and Fergie Jenkins. There were several reasons why those Red Sox never won a World Series, namely the incompetence of manager Don Zimmer and injuries to Fred Lynn and Carlton Fisk, but the main reason may have been their refusal to participate in free agency.

Over the first five years of free agency, their only significant signing was closer Bill Campbell, who had just one good season in Boston before falling off. The Yankees, meanwhile, were the most active team, signing future Hall of Famers Reggie Jackson, Catfish Hunter, Goose Gossage, and Dave Winfield.

Still, the Red Sox were competitive until the disastrous 1980 offseason, when they traded All-Stars Lynn and Rick Burleson to the Angels after failing to sign them to contract extensions. The final straw was when homegrown star Fisk signed with the White Sox after the Red Sox failed to make him a competitive offer.

The Red Sox window of contention was completely shut after that offseason, as they didn’t finish higher than third place over the next five years. Yet they still had future Hall of Famers in Rice and Yastrzemski and added emerging rookies Wade Boggs and Roger Clemens. However, they always seemed to be a few pieces short, a solution that could have easily been fixed by spending some money on free agency.

4: What if Grady Little pulled Pedro Martinez in 2003?

There may have been no better pitcher in baseball history than turn-of-the-century Pedro Martinez. From 1997-2003, Pedro won three Cy Young Awards, led the league in strikeouts three times, and posted a ridiculous 213 ERA+. Yet after a 2001 rotator cuff injury, it became clear that Martinez could not go as deep into games as he once could, and his stats got significantly worse the deeper he went. Red Sox management implored manager Grady Little to take Martinez out at around 100 pitches.

With that in mind, it looked like Martinez’s night was done when he struck out Alfonso Soriano to end the seventh inning of the 2003 ALCS. He was well past 100 pitches, and red-hot relievers Scott Williamson and Mike Timlin, who had allowed a combined one run in the playoffs, were ready to protect a 5-2 lead.

Yet Williams sent Martinez back out for the eight, and, after a pop-up from leadoff batter Nick Johnson, it all fell apart.  Derek Jeter doubled to right; Bernie Williams drove him in with a single; Hideki Matsui hit a ground-rule double; and Jorge Posada tied the game with a two-run, bloop single.

Though the game was only tied, the result felt inevitable. Aaron Boone hit a walk-off home run in the 11th to send the Yankees to the World Series and Grady Little packing.

3: What if Lou Piniella didn’t win his battle with the sun?

What people remember when they think about the 1978 AL East pennant race is the Red Sox blowing a 14.5 game lead to the Yankees and Bucky Dent’s improbable home run to win the one-game playoff. What often gets forgotten is the miraculous defense of Yankee’s right fielder Lou Piniella that allowed the Yankees to win the game.

In the inning before Dent’s home run, the Red Sox had a chance to extend their 2-0 lead with Jim Rice on second, Carlton Fisk on first, and former MVP, Fred Lynn, at the plate. Lynn hit a long fly ball to right field, directly into the late afternoon sun. With limited visibility, Piniella ranged deep into the right-field corner and made a basket catch to prevent two runs from scoring.

The Yankees scored five runs in the top of the seventh and were still clinging to a one-run lead as the Red Sox came to bat in the bottom of the ninth. Rick Burleson worked a one-out walk and looked sure to advance to third when Jerry Remy ripped a line drive to right field.

With the blinding sun in his eyes, Piniella miraculously stuck out his glove and played the ball perfectly on one hop. Burleson was forced to stop at second, and when Jim Rice flew out to deep right-center, he could only advance to third base rather than scoring. Yastrzemski followed with a weak pop-up to third base, finishing off the worst single-season collapse in baseball history.

2: What if the Red Sox signed Willie Mays and Jackie Robinson?

The Red Sox of the ’40s and the ’50s had one of the greatest players of all time in Ted Williams, and yet they could have paired him with two others if not for the racism of their management. In 1945, esteemed columnist Dave Egan pressured both the Red Sox and the Boston Braves to integrate their team.  GM Eddie Collins said that claim was baseless, for the Red Sox had never had a request for a tryout by a black player.

In response to this ridiculous statement, black sportswriter Wendell Smith brought three Negro Leagues players to Boston for a tryout, including future icon Jackie Robinson. By all accounts, the players excelled in the tryout, but the Red Sox refused to sign them. Robinson signed with the Dodgers later that year and helped them become the dominant team the Red Sox never were.

History repeated itself only two years later. At the time, the Red Sox had a Double-A team in Birmingham, Alabama who shared a ballpark with the Negro League’s Birmingham Black Barons. This gave the Red Sox first dibs on all the Black Barons players when baseball finally integrated, including their young star outfielder Willie Mays.

Red Sox scout George Digby loved Mays and had a deal in place to purchase the future Hall of Famer from the Barons for only $4,500. Yet when Digby relayed this to GM Joe Cronin and owner Tom Yawkey, he learned that the team “had already made up their mind they weren’t taking on any black players.” Mays went on to sign with the Giants, and the Red Sox were left to imagine an outfield with Willie Mays in center and Ted Williams in left.

1. What if the Red Sox didn’t sell Babe Ruth to the Yankees?

What else could be number one? Babe Ruth had just spent the 1919 season establishing himself as the greatest home run hitter of a time. He hit 29 home runs in just 423 at-bats, more than 26 other teams in the majors that year. At age 24, Babe Rith was just coming into his own as a hitter and looked ready to lead the Red Sox into the next decade.

Owner Harry Frazee, however, had other ideas. Frazee was in desperate need of cash to finance his plan “No, No Nanette,” and trading Ruth, the biggest star in baseball, would be the quickest way to get some. On top of that, the troublesome Ruth constantly butted hands with coaches and had demanded that his salary double or he would sit out the season.

Whatever the reason, Ruth was sent to the Yankees for a then-unheard-of sum of $100,000. Ruth would smash every power record in his fifteen years with the Yankees and lead them to seven pennants and three World Series titles. The Red Sox, meanwhile, would go on to trade many of their best players to the Yankees in the coming years and not win another World Series for 86 years.