Without much fanfare, this past week saw a significant milestone in Red Sox history pass. It was 20 years ago that ownership of the Red Sox passed from the Yawkey Trust to a group headed by John Henry and Tom Werner
(The official completion of the sale didn't take place until February of 2002, when it was approved by MLB owners and the transaction was ratified. But it was 20 years ago this week that the Henry group emerged as the winning bidders and had their $700 million offer accepted by the trust.).
In addition to it being an extremely wise investment -- which included Fenway itself and 80 percent of NESN - since it's now valued at more than $3 billion, more than quadrupling the sale price in the span of two decades, it's hardly hyperbole to say that the transaction changed the course of Red Sox history.
When Henry-Werner purchased the Sox, the franchise had gone 84 years without winning a championship; since the sale, they've won four titles, more than any team in Major League Baseball in that span.
Ultimately, those World Series, along with the physical rehabilitation of Fenway itself, stands this ownership group's lasting legacy. If the Sox were put up for sale tomorrow, the last 20 years would go down as easily the most consequential and successful in the club's history. If nothing else, consider the same franchise which went nearly a century without winning a championship, has averaged one every five seasons since changing hands. It has never gone longer than six years without winning a World Series under this group.
That's an envious achievement. But of course, it's more complicated than that.
Here's a look at the good and the bad from the last 20 years.
COMMITMENT: While it's fashionable to complain that on occasion the Red Sox haven't gone over the CBT -- or luxury tax -- with their payroll, it's hard to take issue with ownership's willingness to spend.
According to COT's Baseball Contracts from Baseball Prospectus, as measured by the 40-man roster, end-of-season payroll, the Red Sox have ranked among the Top 5 MLB teams in payroll in every year but two in the 20 seasons since assuming control of the franchise. In 14 of those seasons, they've been ranked among the Top 3 and in 10 seasons -- half of their tenure -- they've been either first or second.
In the 20 years since this ownership group took over, only the Yankees have spent more money on payroll -- and notably, have one championship compared to four for the Sox.
The Red Sox are a big market team and have among the highest-priced tickets in the game -- they should, and have, spent commensurate with that status. Anything less would be malpractice on their part.
Not all of an organization's spending can be judged by its major league payroll. There's also been a regular commitment to other aspects of the organization such as international scouting, resources, facilities and investment in scouting and development, as well as the number of scouts, instructors and coordinators it employs. Even as they've built up their analytics department, the Sox continue to employ more scouts than most other organizations.
They've spent freely -- though admittedly, not always wisely -- on some big-name international free agents: Daisuke Matsuzaka, Rusney Castillo, and Yoan Moncada to name three,
It's also difficult to blame them for occasionally pulling in the reins of spending -- as they did in 2020 and to a lesser extent in 2021 -- when it's both financially and competitively prudent for them to re-set their rates. Behaving otherwise and disregarding the penalties -- loss of draft picks, draft capital and international free agent money -- would be irresponsible.
It remains to be seen what the new collective bargaining agreement will feature in terms of spending limits and penalties, and how that impacts future spending. But for now, full credit to the Sox for behaving like the big market force that they are.
Criticism of Fenway Sports Group's other investments (Liverpool, Roush Racing, the NHL's Pittsburgh Penguins) seems a little off-base. Until there's evidence that the Red Sox are not spending as they should precisely because more of FSG's resources and attention is instead being lavished on Liverpool or the Penguins, that seems like nitpicking.
STEWARDSHIP
This category is a little hard to define, but it's an area that Henry and Co. mentioned upon buying the team. Let's face it: owning the Boston Red Sox is different than owning, say, the Milwaukee Brewers or Texas Rangers.
This is an original American League franchise, whose roots date back more than a century. There's history here, and tradition, and this ownership has not only protected the legacy, but it can be argued, enhanced it thanks to four Duck Boat parades.
The Red Sox brand means something, and that was acknowledged when the franchise was transferred. It's also been honored in the 20 years since.
PHILANTHROPY
This one is difficult to measure, because, as a privately held entity, we don't know the exact details of the team's charitable works. We do know that they've been active with the Red Sox Foundation, which in turn, supports such endeavors as Red Sox Scholars, the RBI (Reviving Baseball in Inner Cities) Program, Run To Home Base, and the team's long-time charitable focus, the Jimmy Fund.
Through its support of students, veterans, under-served communities and the medical community, the Sox have, by all accounts, used their resources for good, In that sense, they've carried on the work of the Yawkey Foundation, which demonstrated a similarly philanthropic commitment.
FENWAY
Beyond the four World Series won, the improvements to the ballpark stand as the most obvious and tangible achievement of this ownership group.
It might be easy to forget now, in the latter years of the Yawkey Trust, Fenway had fallen into disrepair, due to neglect. Maintenance slipped, and the ballpark wasn't always clean.
Henry and Co. have injected plenty of resources during a 10-year-long renovation of the game's oldest ballpark. Seats atop the Green Monster, a right field roof pavilion, three new scoreboards, a new video screen, an expanded concourse in right field, new concession stands and expanded offerings are some of the most obvious enhancements.
Other improvements -- renovation of both clubhouses, improved training facilities, the installation of indoor batting cages -- have also been made.
Yes, the reserved seats still lack adequate leg room, and there remains too many obstructed seats. But most of that is a measure of the ballpark's age, and can't be overcome.
In general, the fan experience of attending a game at Fenway is markedly better now than it was before Henry and Co. purchased the team two decades ago, and that's not an insignificant achievement.
INCLUSIVENESS
This can be broadly applied here, and will be.
When it comes to maintaining strong relations with alumni and former members of the organization, this group gets good grades. Repairs have been made with former stars who had grown alienated with the organization. The Red Sox have a long history with a (mostly) proud heritage. It only makes sense to capitalize on that and maintain a link to those who contributed to the team's history.
On the more specific matter of being more inclusive, the team has also shown improvement. Through its hiring of Alex Cora (twice) and promotion of Raquel Ferreira, the team has reached admirable milestones with key positions. Cora is the first person of color to manage the team and Ferreira is among the highest-ranking female executives in the game and those are important firsts for the franchise.
Further, the Sox hired the first person of color female coach in minor league history, and while some may suggest this was mere virtue signaling on their part, they deserve credit for trying to be more inclusive.
Then there's the divisive decision on renaming the street on which the ballpark sits.. Henry himself initiated this, and even if you agree with the decision -- I do, for the most part -- his public comments on the topic were overwrought.
In the end, stripping the Yawkey name proved to be unavoidably controversial, perhaps made worse by Henry's remarks about being "haunted'' by the racism associated with Yawkey's long ownership of the club.
Henry deserves credit for wanting to change the ballclub's legacy. But his handling of the street name change was ham-handed.
AUTONOMY
Here's where things have occasionally gone off the track.
While it's natural for ownership to have some say-so in big decisions, there have been times when Henry, Werner at al have been too eager to place their thumbs on the scale.
In the first few seasons, then-CEO/president Larry Lucchino wanted more input into baseball decisions, which in turn helped lead to Theo Epstein's resignation for the 2005-2006 offseason. After Epstein left for good in 2011, ownership grew more involved with the younger, less experienced Ben Cherington in charge of Baseball Operations.
That resulted in the dreadful Bobby Valentine Experience and the lost year of 2012, followed soon after by the signings of Hanley Ramirez and Pablo Sandoval, two free-agent additions that took place, suspiciously enough, after Werner publicly complained about a lack of star power impacting NESN ratings.
Later, Henry did a 180 and suggested that the organization was too analytically inclined -- at a time when every team in the sport was moving that way. It seemed, at best, a contradictory and counter-intuitive stance.
MESSAGING
This has been, unquestionably, the weakest aspect of the Henry Era.
Of late, Henry has disappeared almost entirely from the public. His last full-fledged media availability was 22 months ago, the day after the Mookie Betts trade was completed.
Henry's point is that he's not comfortable in the spotlight. That's a reasonable enough point to make for a hedge fund magnate; it's less acceptable when you're the principal owner of a franchise that he himself once labeled a "public trust.''
He may not enjoy the give-and-take with reporters. He may feel he's been unfairly depicted in the media.
But the overriding point is, as the primary owner of one of the handful of most famous sports franchises in North America, a certain amount of accountability is expected. Lately, however, Henry only is seen when things are going well. After being out of sight since the Betts deal, he re-appeared in the postseason, present on the field before a handful of games.
Then there's the clumsiness of their partnerships. Did someone not realize that Boston-area sports fans might not be all-in on working with LeBron James? And the purchase of the Penguins has the potential for some awkward interactions at NESN board meetings.
OVERALL
There have been missteps along the way, for sure. But that can probably be said about nearly any sports ownership group, the Patriots included.
But it's also important to see the big picture here. When Henry, Werner and Co, were approved, there were howls that both were carpet-baggers looking to flip the franchise for a quick profit.
Instead, the team -- with a few notable exceptions -- has been immensely successful, enjoying the most success its had since the days of Babe Ruth. Surely, there isn't a Red Sox fan alive who wouldn't have signed on when told the incoming owners would oversee four championships and a (privately financed) ballpark restoration?