Boston Red Sox most controversial figures: Tom Yawkey

In this first look at the most controversial figures in Boston Red Sox history, we look at longtime owner Tom Yawkey and his complicated legacy.

Just as Boston Red Sox history is filled with beloved characters, it’s also filled with its share of, if not outright villains, then at least figures who elicit mixed reactions. Any franchise that has been around for as long as the Red Sox will have their fair share of controversial figures peppering their history;  if anything, the Red Sox may have more littering their past than most other teams.

Some of these controversial figures were the target of fan ire during their time while others grew to be harshly evaluated if not actively disliked with the benefit of hindsight. Some of them made bad decisions, some of them rubbed people the wrong way, some of them said and/or did terrible things, some of them had odious beliefs, and many of them encompassed most of all of those bad qualities.

What follows is the first look at some of the most controversial figures in the long and storied history of the Boston Red Sox. Some of the things that will be discussed will be uncomfortable and in some cases downright abhorrent to read while others will allow us to laugh at the bumbling bad decisions that were made. In all cases, these are parts of the team’s history that cannot and should not be ignored.

The first one we’ll look at is one of the most divisive figures in team history, Tom Yawkey. Born in Detroit, Michigan in 1903, the future longtime owner of the Red Sox inherited his adopted father’s $40 million fortune in 1919 at the age of 16. However, he was unable to access the money until he turned 30 and so young Tom Yawkey had to bide his time.

In 1933, as soon as he turned 30 and got his hands on his money, Yawkey purchased the Red Sox for $1.25 million. Almost simultaneously, he hired his friend Eddie Collins (himself a former major league player for the Philadelphia Athletics) to be his General Manager. Collins would figure prominently in why Yawkey was so controversial during and after his ownership of the team.

From the minute he bought he team, Yawkey committed to making the Red Sox a winner; the team had been a perennial doormat since they sold Babe Ruth to the Yankees in 1920. Yawkey spent money and Collins found talent and by the end of the decade when they signed Ted Williams, things were looking up. Yawkey’s dream was to make the Red Sox World Series champions and he came very close several times, but ultimately ended up short of his goal.

What made Yawkey so controversial was the Red Sox stance on race relations and integrations. The Red Sox were the last team to promote a black player to the major league level, doing so in 1959 a whopping twelve years after Jackie Robinson broke the color line with the Dodgers. Even then, they only did so when threatened by a lawsuit. The Red Sox even had a chance to sign Robinson as well as Willie Mays, and passed on both because of their internal “no black players” policy.

While Yawkey wasn’t directly involved in these decisions (Eddie Collins, Joe Cronin, and Pinky Higgins were all directly responsible), since Yawkey was the owner the ultimate responsibility rested with him. Furthermore, there were other reasons to suspect that Yawkey was more than slightly racist.

He allowed the whites-only Elks Club of Winterhaven, Florida to come into the clubhouse during spring training to pass along invites to only the white players. This led to another lawsuit from former player Tommy Harper after he was fired for complaining about it to the press. Yawkey and his wife Jean also shielded longtime clubhouse attendant and notorious child sexual abuser Donald Fitzpatrick from punishment, refusing to fire him even while knowing of his heinous crimes.

Indeed Fitzpatrick’s predilection for young black boys and the years of sexual abuse he subjected them to between 1971 and 1991 were an open secret among Red Sox employees and even the players, who routinely warned young volunteers in the clubhouse to stay away from Fitzpatrick. Complaints from the abused to Red Sox officials fell on deaf ears and it wasn’t until one brave fan went public in 1991 that Fitzpatrick quit and the Red Sox were forced to admit culpability.

Still, it wasn’t until current owner John Henry bought the team in 2002 that the team settled with the victims. This monstrous scandal, which was the Penn State scandal before the actual Penn State scandal, remains one of the biggest black spots on Yawkey’s entire resume during his longtime ownership of the Red Sox.

Yawkey owned the Red Sox from 1933 until his death in 1976. In 1944, he married his second wife Jean who would inherit the team after he died. She continued to own the team (not without controversy herself) until her death in 1992. The Yawkeys did do some good for the Boston community, strengthening the team’s commitment to fundraising for the Jimmy Fund  and donating a large sum to the Dana-Farber Cancer Institute to build a new cancer center in Boston (which is named after them).

However, there are enough troubling aspects of Yawkey’s ownership of the Red Sox that the team has taken pains to distance themselves from his past, reverting the name of Yawkey Way (which was named after Yawkey in 1977) back to Jersey Street. The city of Boston also renamed the Yawkey Station MBTA Commuter Rail station to Landsdowne Station in 2019.

While Tom Yawkey did a lot of good for the city of Boston and helped turn the Red Sox into a perennial spender and contender, he never realized his dream of winning a World Series. The institutionalized racist policies of the team under his ownership only add to the cloud hanging over his 44 year ownership of the team.