Should The Red Sox Extend Chris Sale For 3 Or More Years Right Now?

We will be delving a lot more into all team payrolls on the MLB Reports as part of our regular features from now on. One of the things that I have been thinking about a lot is the Red Sox Payroll. I wonder if they shouldn’t just extend Chris Sale for an additional 3 years. Yes it is risky with a guy who throws with a whipping motion, but you have a lot to consider on this. First you could offer him a 3 Year deal extension worth about $90 MIL total. It would be an awesome move to align Sale on the same years of service with David Price. IMAGE by Sports Mockery

Chris Sale will enter the year at age 28, and while his current deal will take him to age 31 before he hits Free Agency prior to the 2020 season, maybe the Red Sox could capitalize on him maybe seeking some security.

I am suggesting the starting point of a AAV of $30 MIL.  Maybe the club adds a Mutual Option for the 4th and 5th year of the extension with a Buyout, but this is a smart concept from the Red Sox perspective.

Never in their long standing organization have they had such rich young superstars just entering the league at the same time.

Mookie Betts/Jackie Bradley Jr – and Xander Bogaerts are both under Team Control until 2021 and 202o respectively- with Betts/Bogaerts as perennial MVP contenders.

Even better than that are Andrew Benintendi (2023) and Blake Swihart (2022) rounding out a nice nucleus of talent held for cheap on the longterm.

Chris Sale has been in the top 6 for Cy Young Voting for each of the last 5 campaigns, owning a career record of 74 – 50, with a n ERA of exactly 3 – and a sparking WHIP of 1.065 in his 1110 IP worth of work.  I think this guy has at least 2500 Innings for his career in him.  Why not offer a 3 Years extension worth about $90 MIL from 2020 – 2022, with a few Vesting Options in 2023 and 2024 – that includes some Buyout money?  Sale may jump at the offer for dollar security, and you extend your window of featuring two ace pitchers from the Left side.  Both he and Price are the two top Southpaws in the Amerlcan League right now.

Dustin Pedroia and David Price are the only players on the teams salaried contracts for the books in 2020, the same winter that Sale would enter the open market as a 31 Year Old.

I have always compared Chris Sale to Hall of Famer Randy Johnson.  I am not as worried about his violent pitching motion as others are. 

I for one, thinks it would behoove Dave Dombrowski to lob the extension idea.

If anything, it also prolongs how awesome this trade may end up being if you can rake in a championship or 2.

As these young superstars mature, and you want to extend them, finding ace pitchers on the open market also might prove costly. 

Think of the  Free Agents that were available during this winter.  Ahem..Rich Hill was the best.

More often than not clubs are extending young ace Starters to extensions early enough to have them not hit Free Agency.  That is exactly what the White Sox did with Sale before he became a top pitcher.

Some people caution on signing Starters for more than 5 years, yet we just saw the Nationals extend Stephen Strasburg to a 7 YR Deal worth $175 MIL..

Johnny Cueto signed a 6 year deal for $130 MIL last winter, and Greinke signed his name in the dotted line for a 6 year pact worth $26.5 MIL before his age 32 season, however he may have ended long deals for guys past 30.

Boston may just opt to not extend Sale at any point in the next 3 years, and take their chances in developing another ace pitcher for when he leaves, and David Price starts on the back 9. 

But why not try now when the cost may only accrue about $100 MIL right now.

The Red Six are having a great offsesson despite David Ortiz retiring. Are potentially the deepest all around team in the American League, with the greatest collection of veterans and young players.  Here is the thing though.  With a payroll that is near the Luxury Tax Threshold every year, and the penalties increasing so vehemently, it may be tougher to sign Free Agent ace pitchers going forward like they did with David Price prior to 2016.  Boston should extend Sale to line up the same years of service with Price, and have the young talent all around them for the next half dozen years to contend for multiple World Series Titles.

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