For Boston, Keeping the Band Together Seems Unlikely

The Boston Red Sox enter the offseason with as many questions as anyone. The biggest question? How do they keep this team together for years to come?

The short version of this story is…they won’t.

The Red Sox’s top priority is extending Mookie Betts. Betts is the type of player any organization would want to build around and supposedly John Henry has expressed serious interest in making Betts a Red Sox lifer. Even though he isn’t a free agent until 2021, Mookie will most likely be the next recipient of a massive contract from Boston; however, Mookie won’t—and shouldn’t—sign until Bryce Harper reaches an agreement with his new home. Mookie is a more complete ballplayer than Harper, and he is going to want to be paid like it. Harper’s annual salary is expected to be anywhere from $30 to $40 million per year, and if Betts is expecting more, Boston will need to manage its books accordingly. Keeping Mookie will mean that others will not be able to stay.

So, who leaves? Boston’s big free agents this offseason are Nathan Eovaldi, Joe Kelly, and Craig Kimbrel. Most have already said their goodbyes to Kimbrel, as he is expected to ask for one of the biggest contracts in reliever history. While Kelly’s market is yet to be defined, it’s not unreasonable to think his incredible postseason run will expand his market and price range. There also appears to be a bidding war shaping up for Eovaldi, who according to WEEI’s Rob Bradford garnered interest from everyone and their mother.

It might just be safe to assume Boston loses all of those guys. Three incredibly important pieces to their success in the regular and postseason will be on new teams next year. Lucky for Boston, the reliever market is occupied with less expensive closing options like Zach Britton and Andrew Miller, so finding Kimbrel’s less expensive replacement won’t be impossible. And Kelly’s slot can be filled from within the organization by a guy named Durbin Feltman. Feltman is the team’s 2018 third round draft pick who offers a similar skill set to Kelly and is expected to be with the big league club some time next year. Finding Eovaldi’s replacement won’t be so easy. Starters that throw 100mph with his mental makeup don’t just grow on trees. Please get back to me when you find a replacement for him.

If the idea of losing those three players, or even one of those three, concerns you, then shield your eyes from the upcoming free agents after the 2019 season. Chris Sale, Xander Bogaerts, Rick Porcello, Mitch Moreland, Brock Holt, Eduardo Nunez, and Steve Pearce are all scheduled free agents. This list doesn’t include the almost certain opt out of J.D. Martinez, who has the opt-out clause in place for after the 2019 season. Assuming he doesn’t spend the entire year hurt, he’ll be sure to test the market again and expect a much bigger payday than his last. You guys feeling a slight increase in heart rate after seeing that list? Let’s calm down and digest this.

Martinez is the Robin to Mookie’s Batman. The Red Sox will pay him enough to keep him happy and bashing in Boston. And Sale is the most talented pitcher to start in Boston since Pedro owned the mound. That is as important of a trio as a team can have, and Boston is well aware of that. However, it’s not unrealistic to think Boston will have north of $100 million locked into just those three by the end of next offseason. That doesn’t include the contract of David Price who should make somewhere around $31 million annually until his contract is up in 2022. That’s four players taking up around $140 million. There are 21 more slots to fill out on that opening day roster and only so much money to go around. Moreland, Holt, Pearce, and Nunez are all players that won’t break Boston’s budget if they decide to retain them. And the bats and gloves of Andrew Benintendi, Rafael Devers, Jackie Bradley Jr, and Christian Vazquez are all under team control through at least 2021. That gives the team much needed paycheck flexibility when going after free agents this offseason and next.

There are still two big pink elephants in the room, though. Rick Porcello and Xander Bogaerts are two players that I think will be on different teams by the end of this offseason. With the big paydays coming for Betts, Martinez, and Sale, it seems impossible to assume Boston to will be able to shell out for two more massive contracts. Boston has the opportunity to obtain prospects or even MLB players for the two this offseason. Unfortunately, with only one year of control for both, they will probably need to look to other contenders to make a deal with.

Porcello is a good middle-of-the-rotation pitcher that can help any team looking to make a push at a title next year and could net a decent purse from any contender. If the Red Sox decide that they are trying to deal Porcello, an incredibly intense market could surface for the former Cy Young. One could assume that any team not named the Yankees could make a deal with Boston.

The Bogaerts market will be different. Although the shortstop market isn’t great this offseason after Machado, there really isn’t a need amongst contenders for an all star shortstop, because they all have one. In the AL, the shortstop position is in good hands on basically any team that could make its way into the playoffs next year. But in the NL, there is a team in desperate need of a deep playoff run and a shortstop: the Cubs.

Theo Epstein is reportedly not happy with his group’s under-performance in October, and now, because of Addison Russel’s punishment, he is in need of a shortstop. Theo’s familiarity with Boston and his own angst with his team could provide riveting trade theatre. If a deal between the two actually happens, it could be massive. The Cubs and Sox have seemingly been linked every offseason to a supposed blockbuster, but it’s never happened. This could be the offseason all of those rumors become real life. Boston’s need to fill their own shortstop postition after dealing Bogaerts could rope in multiple teams to this supposed trade and send a ripple effect through baseball.

Boston could, and honestly has the money to, simply throw caution to the wind and re-sign everyone. They’d make me look really stupid for spending hours of my time thinking about what type of package they could get from the Cubs for Bogaerts. I wouldn’t be mad if they did. A $300-million payroll is a small price to pay for a team of homegown stars that can contend for a World Series annually, right? In reality though, Boston has two choices. Take one more shot at a title with the core you have in 2019 and risk losing players to free agency, or trade the two that you know could garner assets for this offseason.

Winning a championship gives Boston all the flexibility they need to make either choice. They have a great problem. They’ve managed to build a team full of stars that’s already won the city a ring. A lot of places wish they were wondering how they were going to keep their World Series Champions together for year to come.

Photo via USAToday


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