By Terry Cushman – @cushmanMLB

For the “Mookie Betts or die” crowd, this will not be a popular idea.   It has been highly publicized since the spring of 2017, that Betts and his agents had turned down a five year $100M extension from the Red Sox.   Earlier in the decade, then GM, Theo Esptein, was very successful in offering Jon Lester, Clay Buchholz, and Dustin Pedroia similarly structured contracts to buy up their arbitration, plus tack on a couple (option) years.   In those previous cases, it was a win-win for all parties.


Where the Red Sox went wrong with Mookie:


Times have changed, and Betts was coming off an MVP runner-up season to Mike Trout.   With his soaring value, it made much less sense for the gold glove right fielder to agree to a “team friendly” deal as some of his earlier Boston alumni had.   He will reach free agency right after his 28th birthday, and could be in line from anywhere from a 6-10 year deal depending on which way the market trends following this year’s free agency class. Bryce Harper and Manny Machado will headline that very class.   Should one or both of them net a $300M deal, it will be inevitable to expect Betts’exceed possibly both of those agreements.

Current MLB superstars such as Madison Bumgarner (5/$35M) Paul Goldschmidt (5/$32M), and Anthony Rizzo (7/$41M), all agreed to team friendly deals, when any single one of them held out for much higher value.   The 5/$100M deal Betts turned down certainly trumps those examples.   Cleveland’s Francisco Lindor also turned down a similar deal to his Boston counter part.

Few people half way through 2016 expected Mookie to make a serious run at the AL MVP award at the end of that season.   He had a .318/.363/.534 slash line with 31 home runs, and 113 driven in.   Offering an extension before the 2016 all star break may have seemed risky at the time, because nobody truly knew what his ceiling was.   However, in hindsight, the Red Sox probably waited a year too long to swoop in and make an offer.  Had the front office done so earlier, it likely would have been too tempting for the Betts camp to turn down, and a deal would have been made.


Now begs the question:    Should the Red Sox focus their efforts on Andrew Benintendi?


Unlike Betts, who was not selected by Boston until the 5th round of the the 2011 draft, Andrew Benintendi was a highly regarded first round pick, who was drafted seventh overall.  Most impressively, Benintendi made an incredibly successful rookie debut only 14 months after being drafted.   His ascension to the majors is one of the quickest in recent franchise history.

If the Red Sox are entertaining this idea at all, Benintendi is essentially at the very same point his opposite corner outfield teammate was in 2016, when suddenly his value started to exceed the point where an extension made little sense in terms of maximization.   The former Arkansas Razorback has four years of team control remaining beyond this current year, which takes him through 2022, his age 28 season.

What type of deal might Benintendi and his agents agree to?    Mike Trout signed a six year, $144M extension after the 2014 season, which works out to an average annual value of $24M per year.  I would personally expect a similar deal for Benintendi around that value.   Perhaps 6/$120 or 7/$140 which would tack on 2-3 years beyond 2022, and to his age 30 season.

The ultimate risk here is that if the Red Sox hold out for Betts once he reaches free agency, and then can’t agree to a deal, they could find themselves in a similar predicament with Benintendi.   The ultimate worst case scenario, is that they miss out on them both.

Many Red Sox fans are fanatical about their favorite players, some of which are well beyond any touch of reality.   Ask yourself this question:   Is Mookie Betts at 10/$400M really going to provide a HUGE difference in production than J.D. Martinez who is playing on a 5/$110 deal at nearly QUADRUPLE the amount?   Definitely not.    There’s a reason the World Series has only been won one single time in it’s long history with a player making north of $200M (Yankees/A-ROD/2009).


“Who cares, the Red Sox have all the money in the world!”


Big contracts come with big consequences, and completely kill whatever financial resources you have remaining to spend on starting pitchers, and bullpen relievers.  Not to mention draft penalties if the team were to exceed the luxury tax beyond two years in a row.   At that point you’re going to miss out on drafting the next Bogaerts or Benintendi.   Those penalties are extremely severe, which is why even richer teams than the Red Sox such as the Yankees & Dodgers, have been working feverishly to get below the luxury tax threshold.

Despite Red Sox Nation currently being high on this year’s “Mookiemania,” it is definitely in the team’s best interest to explore a more inexpensive scenario with Benintendi.   And despite all the sense that it makes, it’s probably less likely to be pursued.  Smart Red Sox fans will always root for the name on the front of the jersey versus the name on the back.

It’s especially frustrating that Mookie Betts won’t even come to the table for a discussion.   The 5/$100M deal that Boston initially offered him, especially compared to the contracts I listed above, was a semi fair deal.   It’s not like the 4/$70 deal they lowballed Jon Lester with, who was 30 years old at the time.

Whichever course of action Boston’s front office takes is anybody’s guess.   But one thing is for certain, they have signed a lot of bad contracts in the past.  And have an extremely poor overall record in the past decade during free agency.




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