Red Sox Offseason Checklist: Priorities, extensions, free agency

BOSTON, MA - JULY 27: Craig Kimbrel #46 of the Boston Red Sox pitches in the top of the of the ninth inning of the game against the Minnesota Twins at Fenway Park on July 27, 2018 in Boston, Massachusetts. (Photo by Omar Rawlings/Getty Images)
BOSTON, MA - JULY 27: Craig Kimbrel #46 of the Boston Red Sox pitches in the top of the of the ninth inning of the game against the Minnesota Twins at Fenway Park on July 27, 2018 in Boston, Massachusetts. (Photo by Omar Rawlings/Getty Images)
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BOSTON, MA – SEPTEMBER 18: Dave Dombrowski the President of Baseball Operations of the Boston Red Sox stands at home plate before a game against the New York Yankees at Fenway Park on September 18, 2016 in Boston, Massachusetts. The Red Sox won 5-4. (Photo by Rich Gagnon/Getty Images)
BOSTON, MA – SEPTEMBER 18: Dave Dombrowski the President of Baseball Operations of the Boston Red Sox stands at home plate before a game against the New York Yankees at Fenway Park on September 18, 2016 in Boston, Massachusetts. The Red Sox won 5-4. (Photo by Rich Gagnon/Getty Images) /

Most of the Boston Red Sox core remains but some key players will hit the open market. What will Boston’s strategy be this offseason?

With about two weeks left in the regular season, the Boston Red Sox are gearing up for a deep postseason run. With a loaded offense, dominant rotation and a deep yet unsettled bullpen, the Red Sox are looking like a true contender. However, it’s never too early to look ahead to the offseason and look at what the Red Sox roster could look like come 2019.

To begin, here is a list of the players who are set to become or could possibly become free agents this offseason.

Nathan Eovaldi

Joe Kelly

Craig Kimbrel

Ian Kinsler

Eduardo Nunez (Player Option)

Brandon Phillips

Steve Pearce

Drew Pomeranz

David Price (Player Option)

Chris Sale (Team Option)

Between the money saved from the impending free agents and the Hanley Ramirez contract coming off the books, the Red Sox are set to free up at least $54,870,000 entering this offseason. This figure does not include Eovaldi or Kinsler who both spent more than half of the season with a different team.

With that being said, let’s hop into the checklist.

BALTIMORE, MD – AUGUST 12: Craig Kimbrel #46 of the Boston Red Sox pitches against the Baltimore Orioles during the ninth inning at Oriole Park at Camden Yards on August 12, 2018 in Baltimore, Maryland. (Photo by Scott Taetsch/Getty Images)
BALTIMORE, MD – AUGUST 12: Craig Kimbrel #46 of the Boston Red Sox pitches against the Baltimore Orioles during the ninth inning at Oriole Park at Camden Yards on August 12, 2018 in Baltimore, Maryland. (Photo by Scott Taetsch/Getty Images) /

Resign Craig Kimbrel and/or acquire another reliever

The good news is that Craig Kimbrel wants to remain in Boston. Kimbrel said in July, “I’ve loved my last three years here. The city’s provided me and my family a lot. And we’re very grateful for that. And we’d love to stay.”

However, the bad news is he may be out of Boston’s price range. Kimbrel will likely look for a decent increase in salary entering next season. He earned $13 million this season but will likely look for north of $16 million this offseason based on the market for relievers. Last offseason, Dodgers closer Kenley Jansen got a 5-year $80 million contract. However, I would be surprised if Boston went that long. I expect that Kimbrel will look for a deal similar to that of Wade Davis who got $52 million over three years.

That being said, Boston could go a different route. For instance, the Red Sox could turn to the free agent market to find a reliever. Boston has options for next season. They could promote either Tyler Thornburg or Matt Barnes to the closer role. Barnes has a tremendous arsenal and has steadily improved since becoming a permanent member of the Red Sox bullpen in 2016. Thornburg, on the other hand, has experience as a closer as he closed for the Milwaukee Brewers before the Red Sox acquired him prior to the 2017 season.

If Boston goes this route, then they would free up money to go after other relief arms. The first that comes to mind for me is a reunion with Andrew Miller who is set to hit the market. Boston was the team that made Miller a full-time reliever in 2012 and he checks of two boxes as both an ace reliever and a lefty, a piece that has been largely vacant from the Red Sox bullpen this season.

Finally, Boston needs to decide what it wants to do with Joe Kelly. The enigmatic reliever seems like someone who Boston should strongly consider resigning but will likely draw a good amount of interest across the league.

BALTIMORE, MD – AUGUST 12: Chris Sale #41 of the Boston Red Sox pitches against the Baltimore Orioles during the first inning at Oriole Park at Camden Yards on August 12, 2018 in Baltimore, Maryland. (Photo by Scott Taetsch/Getty Images)
BALTIMORE, MD – AUGUST 12: Chris Sale #41 of the Boston Red Sox pitches against the Baltimore Orioles during the first inning at Oriole Park at Camden Yards on August 12, 2018 in Baltimore, Maryland. (Photo by Scott Taetsch/Getty Images) /

Start talking contract extensions- Pitchers

The Red Sox have several core players set to hit the free agent market come 2019.

Chris Sale is the first person the Red Sox should look to resign. Sale is currently signed to a very team friendly contract that paid him just $12,500,000 this season and that will rise to just $15 million next season assuming the Red Sox pick up his team option that they would be crazy to not pick up.

Sale will certainly get paid handsomely but the Red Sox have the chance to strike early and sign him to an extension before he hits the open market. Boston needs to make this happen and should open up discussions with Sale sooner rather than later.

Rick Porcello is the other pitcher the Red Sox should consider talking to. Porcello has been so valuable for the Red Sox both on the mound and in the clubhouse. The 2016 AL Cy Young may not rack up the strikeouts or do anything flashy but what he does do is he goes out there every fifth day and performs.

He will likely not get an offer similar to the four-year, $82.5 million offer the Red Sox signed him to in 2015 but I could see Boston offering him a two or three-year contract with an average annual value around the $15 million mark.

BOSTON, MA – MAY 17: Xander Bogaerts #2 bumps forearms with Mookie Betts #50 of the Boston Red Sox after hitting a three-run home run in the fifth inning of a game against the Baltimore Orioles at Fenway Park on May 17, 2018 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)
BOSTON, MA – MAY 17: Xander Bogaerts #2 bumps forearms with Mookie Betts #50 of the Boston Red Sox after hitting a three-run home run in the fifth inning of a game against the Baltimore Orioles at Fenway Park on May 17, 2018 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images) /

Start talking Contract extensions- Hitters

The first batter I would look to re-sign is Xander Bogaerts. The star shortstop is repeatedly overlooked in the conversation of the best shortstops in baseball. Outside of last season when he was playing through an injury that interrupted a tremendous season to that point, Bogaerts has steadily improved each and every season to this point in his career.

The crazy part about this is that he may still get better. Bogaerts broke onto the scene in 2013 as a 19-year-old and will be just 26 years old on Opening Day next season. He has stabilized the shortstop position that prior to him was a revolving door since the Red Sox traded away Nomar Garciaparra in 2004. Between Nomar and Xander, the Red Sox had the likes of Alex Gonzalez, Julio Lugo, Stephen Drew, and Jose Iglesias all playing the position in that time. My point is that great shortstops do not come around all that often. The Red Sox have a keeper here in Bogaerts, so they should make sure to keep him.

The Red Sox next should talk to J.D. Martinez. The reason that he is not above Bogaerts is the aforementioned player option that the Red Sox would hopefully be able to fall back on. I do not need to say much here, anyone who has watched the Red Sox this season realizes how important he has been to this offense. Martinez will likely look to get his salary up to the $30 million figure that he sought this past offseason but he eventually settled for $23,750,000 per year with the Red Sox.

The next priority should be Mookie Betts and I know what you’re going to say. “Bryce, what are you talking about? Mookie won’t be a free agent after next season. Why do we have to worry about him now?.”

Betts may not hit the market after next season but he does after the 2020 campaign. This guy is your MVP. He sets the tone for this team night in and night out. Betts is a dynamic player who does so many things well on the baseball field. The Red Sox do not need to wait until the year before he hits the market to start talking extension with Mookie. I say pay the man.

The only other players set to hit the market that offseason are first baseman Mitch Moreland and fan favorite utility man Brock Holt.

BOSTON, MA – MAY 16: Dustin Pedroia #15 of the Boston Red Sox talks with Red Sox Manager Alex Cora before the game against the Oakland Athletics at Fenway Park on May 16, 2018 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MA – MAY 16: Dustin Pedroia #15 of the Boston Red Sox talks with Red Sox Manager Alex Cora before the game against the Oakland Athletics at Fenway Park on May 16, 2018 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images) /

Figure out what your doing with the right side of the infield

The Red Sox need to figure out what they want to do at first and more importantly at second base moving forward.

Second base appears to be Dustin Pedroia’s for the foreseeable future and rightfully so. Pedroia has had a tremendous career and I hope he gets to finish his career in Boston where it all began.

However, in recent seasons, Pedroia has struggled mightily to stay on the field. When he has been out there, while he is still a good contact hitter, he has lost almost all of his power. He may not be the answer at second base.

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Other options include Eduardo Nunez and Brock Holt. However, Nunez has a player option and it will be anyone’s guess if he will be back or not. In my eyes, Holt is still more valuable as a utility man who moves all around the diamond. Or maybe Boston likes Blake Swihart at second. There is also the often injured Marco Hernandez who has been good for Boston when healthy or Tzu-Wei Lin who has also impressed when with the big league club. In the minors, Michael Chavis could be an option long term as Rafael Devers is likely Boston’s top option at third for the foreseeable future.

At first base, Boston has Mitch Moreland. However, the Red Sox have not seemed convinced that he is really their solution. Moreland has played quite well this season both in the field and at the plate but do the Red Sox see him as their guy at first base? Or do they see him as the guy that they needed to trade for Steve Pearce to cut into his playing time? Additionally, if it is the latter then who do they have as his right-handed compliment? Pearce is a free agent after this season and Boston used to really like Sam Travis but he has not blown the Red Sox away with his performance at the majors. Or do they like Swihart at first long term? So what is Boston’s plan?

ATLANTA, GA – SEPTEMBER 3: Nathan Eovaldi #17 of the Boston Red Sox throws a first inning pitch against the Atlanta Braves at SunTrust Park on September 3, 2018 in Atlanta, Georgia. (Photo by Scott Cunningham/Getty Images)
ATLANTA, GA – SEPTEMBER 3: Nathan Eovaldi #17 of the Boston Red Sox throws a first inning pitch against the Atlanta Braves at SunTrust Park on September 3, 2018 in Atlanta, Georgia. (Photo by Scott Cunningham/Getty Images) /

Figure out who your fifth starter is

Unless an injury occurs, Boston’s 1-4 pitchers in their rotation seem to be locked in with Chris Sale, Rick Porcello, and Eduardo Rodriguez returning. David Price will also probably be back as I would be stunned if he uses his opt-out. He’s unlikely to get more money elsewhere. However, who does Boston see as their fifth starter next season.

Hector Velazquez has pitched well as a spot starter this season. Or maybe they like Steven Wright. However, Wright is naturally going to be a bit inconsistent as a knuckleballer. Plus, Boston has no one to catch him as Sandy Leon, Christian Vazquez, and Blake Swihart have all tried to catch him but it just does not work out for them usually. Brian Johnson is an option but he never seems to pitch more than four innings.

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I would not be surprised if Boston re-signs either Nathan Eovaldi or Drew Pomeranz to be the fifth starter. Or maybe they go to the free agent market to get someone new. The Red Sox could go the route the Tampa Bay Rays did and go with a bullpen day on the fifth rotation spot. What direction Boston goes is anyone’s guess at this point.

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