Boston Red Sox: 15 Most Controversial Player Moves in Franchise History

OK, let's get the Babe Ruth thing out of the way first. Since the sale of Ruth to the Yankees was so egregious, I'm including it in the introduction rather than the body of the slideshow.

Everyone agrees the financing of "No, No, Nanette" in exchange for the greatest ballplayer of all time is not only the most controversial move in Red Sox history, but also in the entire history of Major League Baseball.

OK, suck it up and move on.

I'm also excluding those moves that haven't fully played out yet, including John Lackey, Daisuke Matsuzaka and Carl Crawford.

Presented in no particular order (except the last two), here are my choices.

Losing Carlton Fisk and Getting Nothing in Return

In the late 1970s, Hall of Fame catcher Carlton Fisk supposedly incurred the ire of Haywood Sullivan, then GM of the Red Sox, by attempting to put pressure on Red Sox management to pay players what they deserved.

When Fisk's contract expired at the end of the 1980 season, Sullivan mailed his new contract one day late. As a result, Fisk was technically a free agent and he signed a $3.5 million, five-year deal with the Chicago White Sox, beginning with the 1981 season.

At the time, both the Red Sox and the White Sox believed Fisk was nearing the end. Who knew he would end up playing more seasons in Chicago than in Boston? 

Steve Grad epitomized this deal, writing, "In fairy tale style, the White Sox opened the 1981 season in Boston against the Red Sox and Fisk's eighth-inning, three run-homer propelled the 'Pale Hose' to a 5-3 victory."

In 1985, Fisk enjoyed his most productive season in the majors, hitting 37 home runs with 107 RBI.

He did not retire until after the 1993 season, when he was 46 years old.

But Haywood Sullivan Did Not Stop There…

Losing Fisk in 1980 was not Sullivan's only gaffe.

Sullivan was also the architect of several 1978 personnel moves that led to the infamous collapse, when the Red Sox blew a 14.5-game lead to the Yankees and lost the playoff on the Bucky "Bleeping" Dent home run.

While the starting nine looked strong, Sullivan decimated pitching depth and bench strength by dealing away players like Bernie Carbo, Ferguson Jenkins, Jim Willoughby and Reggie Cleveland, none of whom brought back comparable value.

While much of the blame at the time was laid at the feet of Don Zimmer, his hands were tied by a new ownership group that had borrowed heavily to buy the team and needed a positive cash flow to stay afloat. 

Veteran players—especially those who were perceived as "clubhouse lawyers"— were let go in favor of players who were not eligible for salary arbitration and would thus cost less. While some were traded for other players (usually not value for value), others were merely sold for cash to better the bottom line.

A good example was pitcher Reggie Cleveland, sold to the Texas Rangers on April 18 for $125,000. Cleveland posted an impressive 3.08 ERA with 12 saves in 12 opportunities (he would end up a perfect 25-for-25 in his career). He was the Rangers' best reliever, winning their Rolaids award.

During that time, Spaceman Bill Lee and a few other of the more anti-authority Red Sox formed what they called "The Buffalo Heads," a group of more educated players who were fans of rock music, drank and experimented with pot and other drugs.

Jim Willoughby, Ferguson Jenkins, Rick Wise and Bernie Carbo joined Lee in this group. "These young players came of age in the turbulent and countercultural 1960s and held a distinctly different worldview," wrote Jon Daly of SABR.

In December 1977, Sullivan traded future Hall of Famer Ferguson Jenkins to the Texas Rangers for the immortal John Poloni and cash. Jenkins promptly went 18-8 with a 3.04 ERA for the Rangers in 1978.

Willoughby was upset to learn the Red Sox hired private detectives to follow their players; he made a public stink about it. He was sold at the end of spring training to the White Sox for a figure barely over the waiver-wire price. He managed 13 saves and a 3.86 ERA in Chicago.

World Series hero Bernie Carbo was sold to Cleveland in June 1978. For the rest of the season he posted a .287/.402/.765 stat line for the Indians.

Bill Lee called the owners "gutless" and staged a walkout. He was relegated to the bullpen when he returned. 

At the end of the season, Sullivan responded by dumping the perceived clubhouse dissident in another giveaway trade—in this case, to the Montreal Expos for Stan Papi. Lee won 17 games in 1979 for the Expos.

Sullivan capped off his 1978 season by allowing beloved pitcher Luis Tiant to leave for the Yankees as a free agent.

Tiant in pinstripes? C'mon!

As a final indignity to cap off this year of ineptitude, Sullivan thumbed his nose at Red Sox Nation by choosing his son, Marc Sullivan, in the second round of the ensuing draft. Marc was considered to be low-round talent, and lived down to the expectation by batting a hefty .186 with 92 strikeouts in 360 major-league at-bats.

I call Sullivan's cumulative efforts in and around the 1978 season a personnel disaster.

Bronson Arroyo for Wily Mo Pena

Back in 2006, the Red Sox traded Bronson Arroyo, a young, quality arm for right-handed power threat Wily Mo Pena.

Despite hitting .301 with 11 HRs in 276 ABs for the Red Sox in 2006, Pena was traded to the Washington Nationals in August of 2007.

He never fulfilled the prophecy of becoming the right-handed David Ortiz. As soon as major-league pitchers realized that Pena couldn't hit a curve ball, he was toast.

According to the Baseball Index, Pena is 8.5 runs above average on fastballs for his career, but a combined minus-18.3 on curves and sliders for his career. 

Meanwhile, Arroyo went on to anchor the Reds rotation (12-plus combined FanGraphs WAR). While his W-L record and ERA have been average, he has certainly been a reliable innings-eater. Arroyo has started at least 32 games for eight seasons in a row, and for the Reds he has averaged 214 innings per year—well over six innings per start.

Cincinnati signed Bronson Arroyo to a two-year extension last season after going 17-10 with a 3.88 ERA in 2010. 

From 2006 to 2010, Wily Mo was traded again, released three times and hasn’t played in a major-league game since he hit .205 in 195 at-bats with the Nationals in 2008. 

Last year, after pounding minor-league pitching, Arizona called Pena up from Triple-A to DH during interleague play. There was even a grassroots effort to have him selected as an NL participant in the Home Run Derby at the 2011 All-Star Game.

Once again, Pena learned the difference between the majors and Triple-A. He struck out 19 times in 46 at bats to a tune of .196. Five of his nine hits were home runs, however.

Signing Julio Lugo to a Four-Year Contract for $36 Million

Enamored by how well Julio Lugo played against the Red Sox when he was with Tampa Bay, GM Theo Epstein signed him to a four-year, $36 million contract in December 2006.

Two-and-a-half years later, without $13.5 million still due Lugo, the Red Sox's designating  the underachieving shortstop for assignment in July of 2009.

Admitting that the signing was an expensive mistake, Epstein told Ian Browne of MLB.com that, "Sunk cost is the sunk cost. This was one of the free-agent signings that didn't work out and we ended up paying for past performance, not current performance."

After hitting .308 for the Rays in 2006, he was signed to be Boston's leadoff hitter. Lugo struggled early in his first season and was relegated to the bottom of the order, where he stayed. 

But the bigger issue was his defense. Yes, the Red Sox did win the 2007 World Series with Lugo at short, but it was in spite of his .968 fielding average with 19 errors. And things just went downhill from there.

The following year he fielded .945 with 16 errors in half as many chances in a season cut short by injury.

During his tenure in Boston, his range factor decreased year by year: 3.96 to 3.41 to 3.21. At the time of his release, range factor had dropped to 2.81 (league average 4.36), and he was fielding .928 with seven errors in 97 chances. 

In March of 2009 Dan Lamothe of Red Sox Monster called Lugo "the least popular player on the Boston Red Sox since 2007," saying "Lugo has done almost nothing since to justify his contract. His fielding has sporadically been atrocious, his hitting has been pathetic given his contract (a Rob Deer-esque on-base percentage of .294 in 2007)." 

Jeff Bagwell to the Astros for Larry Andersen

The Red Sox had the choice of trading either Scott Cooper or Jeff Bagwell to get a fresh arm for the 1990 pennant run. GM Lou Gorman picked the wrong guy and ended up on the short end of what many describe as the most lopsided trade in trade-deadline history.

In return for Larry Andersen, the Houston Astros got Jeff Bagwell. After spending the remainder of the 1990 season in the minors, Bagwell won the first base job out of spring training in 1991 and went on to win the NL Rookie of the Year, batting .294 with 15 home runs and 82 RBI.

Bagwell matured into one of the most feared sluggers in baseball throughout the 1990s, making four All-Star appearances and winning the NL MVP in 1994. He finished his big-league career as a bona fide Hall of Fame candidate, posting a .297 career average with 449 HR, 1529 RBI and 202 stolen bases.

Andersen made 15 relief appearances with the Red Sox at the end of the 1990 season, posting a 1.23 ERA. However, he was ineffective in the playoffs and left for San Diego as a free agent after the season.

1971 Trade of Jim Lonborg, George Scott, Ken Brett, Billy Conigliaro to Brewers

Lonborg, Cy Young award winner and hero of the 1967 "Impossible Dream" Red Sox, did well with the Brewers and had 17- and 18-win seasons with Philadelphia. From 1972 to 1979 he went 89-72 with a 3.79 ERA and 1.31 WHIP.

George Scott hit .306 with 107 RBI in 1973 for the Brewers, then led the league in with 36 home runs and 109 RBI in 1975. (Suffering from seller's remorse, the Red Sox compounded the problem by trading Cecil Cooper to get Scott back, just in time for his production to cease.)

Brett appeared in 270 games for eight teams in the 10 seasons after the trade, including 34 starts, seven complete games and 224.2 innings for the White Sox and Angels in 1977. He closed out his career with 22 relief appearances for the Royals in 1981.

Meanwhile, Pattin did pitch a ton of innings for the Red Sox in 1972 and 1973, starting 65 games and going 32-28 with a 3.73 and 1.28 WHIP. He was traded to Kansas City after the 1973 season for Dick Drago, thus indirectly providing some return.

Tommy Harper had one good year, hitting .281 with 17 home runs while leading the league with 54 stolen bases in 1973. He fell off to .237 the following year and was traded to the Angels for utilityman Bob Heise.

Krausse pitched 60 innings for Boston with an ERA of 6.38 and was cut after one season. Skrable never made it out of the minors and did not pitch at all in the Red Sox organization.

Trading Dave Henderson to the Giants for Randy Kutcher

10 months after being toasted by all of Boston for his 1986 postseason heroics, Dave Henderson was traded to the Giants for a player to be named later. That turned out to be pinch-running utility outfielder Randy Kutcher.

Henderson is best known for his two-out, two-strike, go-ahead home run off Donnie Moore in the top of the ninth inning that crushed the California Angels (and many think led to Moore's suicide in 1989).

The Angels had been one strike away from the World Series when Henderson produced one of the most memorable plays in Red Sox history. He then hit a game-winning sacrifice fly to win the game in extra innings. He went on to hit .400 in the World Series against the Mets, and had it not been for the miraculous Mets rally, he would have also won the Series for the Red Sox with his go-ahead homer off Rick Aguilera in the 10th inning.

Ah, but by the following summer, that was yesterday. Henderson was hitting only .234, so the Red Sox let him go, in part to make room for Ellis Burks.

After playing just 15 games for the Giants, Henderson became an All-Star for Oakland, helping the A's beat the Red Sox in the 1988 and 1990 playoffs. From 1988 to 1991 Henderson hit .275 and averaged more than 20 home runs and 80 RBI per year. He also made one All-Star team.

In 1988 he hit .304 with 24 home runs and 94 RBI, batting .375/.412/.625 against the Red Sox in the ALCS.

He missed almost the entire 1992 season with an injury, but came back to post one more decent year in 1993. Henderson played his final year with Kansas City in 1994, hitting .247 in 62 games with the Royals.

Meanwhile, Ellis Burks hits 94 home runs for Boston in the six years after the trade, while Hendu slams 109.

Kutcher was just a footnote to this story, batting only .224 in 277 plate appearances from 1988-90.

Trading Jamie Moyer to the Mariners for Darren Bragg

What was Dan Duquette thinking? In 1996, Jamie Moyer started the season 7-1 in 10 starts. Duquette then traded Moyer to Seattle for backup outfielder Darren Bragg.

Moyer went 6-2 the rest of the way, making his record 13-3. He led the majors in winning percentage (.813). In 1997, Jamie Moyer went 17-5 with a respectable 3.86 ERA. The next three years he went 42-27. 

OK, so no one could have guessed that Moyer, already long in the tooth when traded, would pitch 11-plus seasons with Seattle including a pair of 20-win seasons. And that he would go to the National League and win another 51 games for the Phillies.

Since the Red Sox traded him, Moyer has won another 206 games before temporarily shutting it down for Tommy John surgery.

Ken Rosenthal tweeted that Moyer—who turns 49 in a couple of weeks and is coming off Tommy John surgery—threw for scouts in San Diego recently and that the scouting report was “excellent.”

By comparison, Darren Bragg is now 42, seven years removed from his last major-league game. In his career, he hit .255 with 46 home runs, 260 RBI.

To be fair, Bragg was not a total bust. He did OK with Boston, hitting .264 for the Red Sox over two and a half seasons with 20 home runs and an OPS hovering close to .750. He then played all over: St. Louis Cardinals (1999), Colorado Rockies (2000), New York Mets (2001), New York Yankees (2001), Atlanta Braves (2002-2003), San Diego Padres (2004) and his final team, the Cincinnati Reds (2004).

Trading Fred Lynn and Steve Renko for Frank Tanana, Jim Dorsey and Joe Rudi

On January 23, 1981, Boston broke up what was arguably the best outfield in baseball (Jim Rice-Fred Lynn-Dwight Evans) by trading Fred Lynn to the California Angels. The Red Sox got Frank Tanana, Jim Dorsey and Joe Rudi in return, and also threw in journeyman pitcher Steve Renko.

“I kept telling the (Red Sox) organization I did not want to be traded,” Lynn told The Boston Globe in 2004.

He continued:

"

They thought I was going to play out my option and be a free agent. I said that’s not what I want to do – I want to stay here. Why would I want to leave a park where I hit .350. It just doesn’t make any sense. Once it got into ownership’s mind, no matter what I said it wasn’t going to work out. They thought they would get something for me so they made the trade.

"

During his seven-year Red Sox career, Lynn batted .308 with 124 home runs, 521 RBIs and a .383 on-base percentage. He won four Gold Gloves in center fielder for the Red Sox. He was a career .347 hitter at Fenway Park with a .420 on-base percentage.

Away from Fenway, he never hit over .300 again. Lynn did go on to hit more than 20 home runs in six consecutive seasons starting in 1982, and was selected MVP of the 1982 ALCS, the first MVP ever selected from the losing team.

In 1983 he was chosen for the All-Star team for the ninth consecutive year, and he hit the only grand slam in All-Star history. His four home runs in All-Star games is second only to Stan Musial.

Tanana was a bust in Boston, earning only four victories against 10 losses before being granted free agency at the end of the 1981 season. Dorsey pitched a total of eight innings for Boston and gives up 15 runs for a 16.88 ERA. Rudi hit .180 in 49 games for the Red Sox.

All in all, this was a disastrous deal for the Red Sox, but also for Fred Lynn personally. Some believe Lynn would have gone on to become a Hall of Famer if he had remained with the Red Sox for his entire career.

In fact, in 1981  Lawrence Ritter and Donald Honig included him in their book The 100 Greatest Baseball Players of All Time.

Freddy Sanchez to Pittsburgh for Jeff Suppan

At the 2003 trade deadline the Red Sox, seeking to add an arm for the playoff run, traded top infield prospect Freddy Sanchez (along with LHP Mike Gonzalez) to the Pirates for pitchers Jeff Suppan, Scott Sauerbeck and Anastacio Martinez.

Both players the Red Sox gave up are still active and productive in MLB. All three players the Red Sox received are out of baseball.

Sanchez blossomed in Pittsburgh, hitting .344 and winning the batting crown in 2006. He has since won a World Series with San Francisco and enters the 2012 season with a lifetime batting average of .297.

Gonzalez was quite successful in his younger days as the closer for the Pirates and then the Braves. His career was somewhat derailed by Tommy John surgery, but he is still in demand. According to a December report by Jon Heyman of Sports Illustrated, the Yankees are interested in him as a left-handed arm out of the bullpen.

From the Red Sox side, Suppan was a bust, producing only three wins and a 5.57 ERA during his 11 appearances for Boston. He was left off of the postseason roster. He last pitched for the Cardinals in 2010.

With Boston, Sauerbeck pitched in 26 games and made one postseason appearance. He threw his last major-league pitch for Oakland in 2006.

During his two stints with Boston in 2004, Martinez made 11 relief appearances, going 2-1 with an 8.44 ERA and one save. He never pitched in the majors again.

Cecil Cooper to the Brewers for George Scott and Bernie Carbo

On December 6, 1976, the Red Sox traded first baseman Cecil Cooper to Milwaukee, getting back two former Red Sox heroes, George "Boomer" Scott and Bernie Carbo.

Five seasons earlier, the Sox had traded Scott because they felt Cooper was their first baseman of the future.

"

"Cooper, however, was taking longer to develop than the Red Sox front office had originally hoped," wrote one Boston blogger, "And when Scott put up some decent numbers for the Brewers, they jumped at the opportunity to bring Boomer back to Boston."

"

While the Red Sox did get some immediate return from the deal, their happiness was short-lived. Scott did hit 33 home runs with 95 RBIs in 1977, but in 1978 his average dropped to .233, and he hit only 12 home runs with 54 RBI. Scott was out of the big leagues a year later.

Carbo did OK in 1977 as well, hitting .289 in 86 games with 15 home runs. But he was sold to Cleveland the following June.

Meanwhile, Cecil Cooper was on his way to becoming a legend in Milwaukee.

In his first three years in Milwaukee, he hit .300, .312 and .308. In 1980 he hit for a .352 average, with 25 home runs, 219 hits and he led the American League with 122 RBI and 335 total bases.

These accomplishments went almost unnoticed because Royals third baseman George Brett flirted with a .400 batting average, setting for.390.

Cooper hit .300 or higher every year from 1977 to 1983 and won the Silver Slugger Award for three straight years. He was named to five American League All-Star teams from 1979 through 1985. He led the AL with 44 doubles in 1979 and 35 doubles in 1981. He also led the AL with 122 RBIs in 1980 and 126 RBIs in 1983.

Cooper also posted three seasons with 200-plus hits (1980, 1982 and 1983). An excellent defensive first baseman, he was a two-time Gold Glove winner (1979–80). 

Former Milwaukee player-coach Sal Bando once said of him, "Cecil Cooper can beat you with a home run or a flare to left or a bunt. And he can field his position. You have guys who can hit home runs and guys who can hit singles. But not many can do both. Cecil can."

During Cooper's 11 years as the Brewers first baseman, the Red Sox used Scott, Bob Watson, Tony Perez, Dave Stapleton and Bill Buckner at first. 

David Murphy, Kason Gabbard and Engel Beltré Traded to Texas for Eric Gagné

Anyone know a major-league team that needs a right fielder?

The Red Sox would have had a pretty good one had they not traded David Murphy to the Rangers in 2007 as part of a deal that brought the unforgettable Eric Gagné to the Red Sox.

Gagné was terrible. In his first 15 appearances, opponents clobbered him at a .350 clip. He allowed 14 earned runs in 14 innings with three blown saves. 

Fans learned to cringe when they saw him coming out of the bullpen. At no time was this more obvious than Game 2 of the 2007 ALCS, when Gagné was brought in to start the 11th inning. Gagné took the loss after allowing the first two runs of a 7-run inning.

Mike Freeman, National Columnist for  CBSSports.com described it this way:

"

When pitching plague Eric Gagne was called on by Terry Francona in the crucial 11th inning, Gagne seemed to have a look on his face that said: "Who, me? You serious?"

Out he trotted and Fenway Park collectively lost its lunch knowing what was going to happen next. The only thing missing was Gagné carrying lighter fluid and matches. Or a swarm of locusts.

"

If Theo Epstein could undo one trade, it would probably be this one.

The Red Sox also gave up pitcher Kason Gabbard and talented headcase minor-league outfielder Engel Beltré. They are not missed, but David Murphy certainly is.

He is a lifetime .280 hitter with a .786 OPS.

Trading Sparky Lyle to the Yankees for Danny Cater and Mario Guerrero

How many times did that deal come back to bite the Red Sox?

Just before the start of the 1972 season, the Red Sox traded their young closer Sparky Lyle to the Yankees for Danny Cater, a soon-to-be 32-year-old outfielder/first baseman, and utility infielder Mario Guerrero.

Guerrero spent only two years with Boston and hit .241.

Mike Bogen of MassLive.com characterized Cater as one "who played first, third and the outfield with equal mediocrity…he'd shown no power (49 homers in 917 games through '69), no speed (25 stolen bases in 54 attempts) and he wouldn't take a walk (193 in 3,446 plate appearances)." 

Cater played only  211 games for Boston over the next three years. To be fair, he did hit .313 in 63 games in 1973.

Before the trade, Lyle had notched 64 saves for Boston from 1969 to 1971, and he was still only 26. After the trade, he saved 35 games for the Yankees in 1972, an American League record at the time and a major-league record for left-handers.

In 1972, Lyle also became the first lefty to collect 100 saves in the American League. He also finished third in the 1972 MVP voting.

Quite simply, he became the Yankees' bullpen ace, establishing himself as one of the best relief pitchers of the 1970s. He helped the Yankees win three straight pennants from 1976 to 1978, and he was instrumental in their World Series victories in 1977 and 1978.

He won the Cy Young Award in 1977, appearing in a league-leading 72 games with 26 saves and a 2.17 ERA. He posted a 13-5 record while pitching 137 innings.

After the 1978 season, he became the gift that keeps on giving when the Yankees traded him to Texas in the deal that brought Dave Righetti to New York.

Lyle finished his 16-year career with 238 saves, a 2.88 ERA and a record of 99-76 in 899 games pitched—all in relief.

Trading Tris Speaker to Cleveland in 1916

One of Boston University’s most sought-after experts on American politics is Tom Whalen, College of General Studies associate professor. Whalen is also a student of baseball history, and he believes the trade of Tris Speaker was the single most important transaction in Red Sox history.

“The Tris Speaker trade was more important than the Babe Ruth trade,” he argues.

First, some background.

The Red Sox won the World Series in 1915, but after the season, Speaker had a falling-out with Red Sox president J.J. Lannin, who wanted Speaker to take a pay cut. Lannin criticized his star's performance, citing his batting average drop from .338 in 1914 to .322 in 1915 as the reason Speaker should take a pay cut from about $15,000 to about $9,000.

Speaker refused, so Lannin dealt Speaker to the Cleveland Indians for Sam Jones, Fred Thomas and $50,000. Not only that, but an angry Speaker held out for $10,000 of the cash Lannin got as part of the deal. After the intervention of AL President Ban Johnson, he got it.

Speaker’s contract with Cleveland for $40,000 was the highest in baseball at the time.

Speaker had led the Red Sox to two World Series championships, and after the trade he carried the Indians to that team's first ever championship. Speaker hit over .350 in 10 of his 11 years with Cleveland, and in 1916 he ended Ty Cobb's run of nine straight AL batting titles by hitting .386 to Cobb’s .371. 

At the time, Speaker and Ty Cobb were considered the best outfielders in the game. Speaker's fielding glove was known as the place "where triples go to die." As a center fielder, Speaker played so shallow for most hitters that he was like a fifth infielder.

His record of unassisted double plays by an outfielder is one that will never be broken.

At least once in his career, he was also credited as the pivot man in a routine double play.

At the time of the trade, Speaker was a .337 hitter and a one-time MVP (1912). He stole 52 bases in 1912, a record that stood until Tommy Harper broke it in 1969.

On the other side of the trade, Sam Jones appeared in only 21 games in 1916 and 1917. He entered the rotation in 1918, and finished with a career 64-59 record, along with a 3.39 ERA.

Thomas played in just 44 games for the Sox in 1918, batting .257.

Speaker, known as "The Grey Eagle," is fourth all-time in career batting average (.345), fifth in hits (3,514) and first in doubles (792). He was elected into the Baseball Hall of Fame in 1937, just the second class ever. And the Red Sox dumped him.

Now for the rest of the story.

“This was the opening Babe Ruth was waiting for,” says Whalen. Young Ruth was an outstanding left-handed pitcher but “he always loved to hit, and he pressured managers to put him in more games [as an outfielder] when he wasn’t pitching,” Whalen says.

Without Speaker’s offensive firepower in the lineup, the Red Sox granted Ruth his wish. By 1918, Ruth’s at-bats nearly tripled—and his RBIs more than quadrupled. 

Then, Whalen contends, “Lannin inadvertently caused the Ruth trade.”

Lannin sold the Red Sox to Harry Frazee in 1916, accepting an IOU for half the sale price. By 1919, Frazee still owed Lannin $250,000. Whalen says "Lannin applied pressure, forced Frazee to come up with the money. Where could Frazee go? He went to Jake Ruppert, owner of the Yankees.”

Frazee sold Ruth to Ruppert for $125,000. “So Lannin was responsible for the two trades that had the biggest repercussions for the club for generations,” says Whalen.

Not Signing Jackie Robinson When They Had the Chance in 1945

That blue number 42 among the retired numbers at Fenway Park could have been a red number had it not been for rampant racism within Red Sox ownership and management.

On April 16, 1945—the day before the start of the regular season—three Negro League ballplayers were given a tryout at Fenway Park. They were Sammy Jethroe, star center fielder for the Cleveland Buckeyes, Philadelphia Stars infielder Marvin Williams and shortstop Jackie Robinson of the Kansas City Monarchs.

Sadly, the tryout was a farce, scheduled by the Red Sox only because City Councilor Isadore Muchnick threatened to revoke their privileges to use Fenway Park on Sundays unless they considered signing black ballplayers.  

Before he died, Muchnick revealed the Red Sox insistence that the event take place in secret, with no reporters present, according to a detailed account of the tryout accord to a report originally published in the Massachusetts Historical Review, volume 6, 2004. 

This media blackout may at least partially explain the contradictory accounts that later appeared in the Boston press, because the reporters all got their information secondhand. There are no photos known of these tryouts. 

In his book, Red Sox Century: The Definitive History of Baseball's Most Storied Franchise, Glenn Stout wrote that the tryout lasted about an hour and a half. In addition to taking ground balls and shagging flies, the players took batting practice.

Robinson later recalled, "I still remember how I hit the ball that day, good to all fields. What happened? Nothing."

Muchnick recalled, "You never saw anyone hit the wall the way Robinson did that day." 

According to one report, only team officials were in the stands, and someone yelled, "Get those n–ggers off the field."

Muchnick claimed that Joe Cronin attended the tryout and said, “When the workout ended I remember going over to Cronin . . . He said to me 'If I had that guy on this club we’d be a world beater,'” but added that the Red Sox couldn’t send Robinson to one of their farm clubs, then all in the South.  

Aaron Stilley wrote that Boston coaches said the right things after the tryout, that they were “impressed” and the players “looked good,” but to no one’s surprise, none of them were pursued by the Red Sox.

According to Stout, "Robinson reserved a particular and lasting enmity toward the Red Sox."

In the final days of the 1967 season, Robinson spoke at a dinner in upstate New York. A UPI reporter asked about the close four-team (Minnesota, Chicago, Detroit and Boston) pennant race. Robinson said “Because of Boston owner Tom Yawkey, I’d like to see them [the Red Sox] lose, because he is probably one of the most bigoted guys in baseball.” 

…or Willie Mays in 1949

And Willie Mays could have been roaming the outfield for Boston instead of the Giants.

Even after Robinson integrated the majors, the Red Sox continued to reject black players. 

The Red Sox had a strong presence in Birmingham because Boston’s Double-A team was the Birmingham Barons of the white Southern Association. Their GM told Boston about a phenomenal prospect on the Birmingham Black Barons whose contract could be bought for only $5,000. The Red Sox's local scout echoed the rave reviews, bringing a reluctant senior scout, Larry Woodall to the scene.

After a few days of inclement weather in Birmingham, Woodall left without seeing Mays.

In a 2002 report on NPR, Juan Williams reported:

"

"One of the team's scouts decided that it wasn't worth waiting through a stretch of rainy weather to scout any black player. That decision killed the possibility that Mays and Ted Williams might have played in the same outfield for the Red Sox."

"

Two years later, Mays was a New York Giants star and the National League Rookie of the Year.

Mays himself thought he was going to Boston. Mays told Howard Bryant of ESPN.com:

"

There's no telling what I would have been able to do in Boston… They had a guy come down to look at me. They had a good team with [Mel] Parnell and [Vern] Stephens, and of course, Ted. But for that [Tom] Yawkey. Everyone knew he was a racist. He didn't want me.

"

I rank the Robinson and Mays non-signings as the worst personnel decision (other than the sale of Babe Ruth) in Red Sox history. The ramifications are obvious.