Did Sam Kennedy Single Handedly Destroy a Dynasty?

Who gave the order?

Hyman Roth famously said, "I didn't ask who gave the order because it had nothing to do with business!" Well, I'm asking. The long, slow decline of the Red Sox since the 2018 championship most likely had everything to do with business.

Sam Kennedy and Theo Epstein were classmates in the Brookline High School Class of '91. They both chose a career in baseball and were both hired by Larry Lucchino in the late 90s with the San Diego Padres. Lucchino mentored both men, Kennedy on the business side and Theo on the baseball ops side. He brought both with him to Boston when FSG bought the Red Sox in December of 2001.

Epstein went on to have a legendary career as a general manager and president of baseball operations, both with the Red Sox and Cubs. In Boston, he not only won two World Series, but his drafts built the home-grown talent that helped win two more.

Kennedy rose up the ladder on the business side, working to expand the footprint of Fenway Sports Group and Fenway Management. He was instrumental in turning FSG into a powerhouse franchise owner, acquiring Liverpool FC, RFK Racing, the Pittsburgh Penguins, and Boston Common Golf. When Lucchino retired in 2015, Kennedy was slated to replace him, but the Red Sox hired Dave Dombrowski and gave him full control of baseball operations. In 2017, Kennedy was named CEO of the Red Sox. He is now CEO of FSG as well.

Dombrowski took the home-grown players drafted by Epstein and Cherington and traded for proven stars using minor league talent. He is known for his "win now" approach, and it worked. His ultra talented team won the World Series in 2018. Just 10 months later, with the team 9 games over .500, he was fired. Most believe the team was not happy that he had cleaned out the farm system and they were looking for a more "sustainable" approach. Here is the first time I ask, "who gave the order?"

Sam Kennedy was now firmly in control of the team and hired Chaim Bloom, formerly of the Tampa Bay Rays. He was known as a draft guru and farm system builder. Simply put, his directives were to rebuild the farm, reduce payroll, and build a competitive major league team. The Red Sox had many bloated contracts under Dombrowski, and Bloom's first order of business was to shed payroll. Dombrowski had just signed Sale and Eovaldi to big contracts. Bloom traded away MVP Mookie Betts (who was due for a huge pay day) and David Price. Who gave the order? You get where I'm going with this.

Once the payroll was lowered, Bloom was given some latitude in signing free agents. This resulted in long term contracts for Trevor Story and Masataka Yoshida. Both contracts have been disastrous. Xander Bogaerts was a free agent at the end of the 2022 season and fans (still stinging from the Betts trade) expected Bloom to sign him to a long-term deal. That didn't happen and Bogaerts signed with the Padres for $280 million. Bloom did sign his one remaining star, Rafael Devers, to a $313 million contract which appeased the fans somewhat. Who gave those orders?

Chaim Bloom was fired after the 2023 season with a record of 272-274 and one playoff appearance in 2021. He did draft the current crop of young stars (Anthony, Mayer, etc.) but was never able to build a winning major league club. Some say he was given an impossible mission, and I would tend to agree. Draft, build a farm, lower payroll, and win. Pretty tough in today's MLB climate.

Sam then hired Craig Breslow and by all accounts he was well down the list of choices as nobody really wanted to step into the impossible situation that Bloom got himself into. Breslow has been given some payroll flexibility but was instructed to trade Devers because despite being one of the best hitters in MLB, "he wasn't a team player." We know who gave that order.

So back to the question "Did Sam Kennedy Single Handedly Destroy a Dynasty? Make no mistake, John Henry owns the team and the buck stops with him, but I seriously doubt he makes baseball decisions. I think he did give direction on the payroll, and he has shown that he does not want to exceed the CBT threshold where he would have to pay penalties. My take is that under Bloom and Breslow, Kennedy was the one making the financial decisions, and sometimes the on-field decisions. He was not going to pay Betts and Bogaerts. He wanted to shed Devers’ salary and used his refusal to play 1B as a convenient excuse. The team is now devoid of stars (save Crochet), and it will be some time before the youngsters develop into the kind of players that can lead a team to a championship.

So yes, Michael Corleone gave the order to whack Moe Greene and Sam Kennedy gave the orders to decimate what was once a proud franchise. He has done this systematically over the last 6 years. In that same time FSG has flourished and he has made himself and John Henry a fortune. Sam talks a good game, routinely saying that he is laser focused on building a winner. As Frankie Pentangeli would say "It's all lies!" Sam is firmly in control of the puppet strings. While I am excited to see what the rookies and second year players can do, I have no confidence that Breslow (or whoever takes his place) will be allowed to have the resources to build a championship team going forward.