Contract Extension Potentially in the Works for Red Sox – Benintendi the Target?

Early yesterday morning (12:41am to be precise) Evan Drellich of reported that the Red Sox are in contract extension discussions with one of their core players. Its very strange to have this kind of rumor surfacing, as usually the player is known but the details are not. The speculation is everywhere. Over The Monster and’s Matt McCarthy mention Mookie Betts as the potential “mystery player”. MLBTradeRumors comment thread (which is always amusing, yet insightful) appears to strongly believe that it must be Andrew Benintendi or Eduardo Rodriguez as they make the “most sense” to many readers. Before the details come out, lets speculate!

Mookie Betts

I’ll start with the most intriguing topic of discussion. Are the Red Sox about to open up their wallets (very wide I might add) and float an offer out to Mookie Betts? I suspect that the minimum offer that would entice Betts to come to the table is 12 years and $350 million and the final pact would likely be higher.

Why this makes sense for Mookie Betts: Completely my speculation by the slow and tempered nature of this off-season and the few prior, but the market has changed and slowed drastically under the new CBA. Teams are avoiding those luxury taxes and Signing a #5 starter now in mid-large size markets seems to cost 1 year and $8 million whereas in the past teams usually took a few flyers on guys around $1-2 million each with incentives. The big guys (Bryce Harper & Manny Machado this year; J.D. Martinez last year) have sat on the open market longer then expected. The best contracts seem to go to those getting their deals done quickly before the market develops. Look at the deal Joe Kelly was able to secure? This market is highly unpredictable and with even a small injury in 2019 or 2020 that regresses his progression slightly, Mookie Betts could find himself not getting paid the way he could right now. Dustin Pedroia‘s contract which was supposedly so “team friendly” is now a problem due to unforseen circumstances, and good on Dustin for taking the security when he did. Perhaps Mookie and Dustin had a conversation about loyalty, leadership and what it means to be a career Red Sox?

Why this makes sense for the Red Sox: The Red Sox need Mookie Betts to be the center of this team moving forward. Dave Dombrowski is not the GM that lets Mookie Betts caliber players slip away in free agency. With the Eovaldi signing, Dombrowski can resign Betts and count on that Betts, Bentendi, Devers, Eovaldi and Price will be the anchors of this team moving forward. That’s a core that any general manager can build around if they are all performing.

Why I don’t think it will happen: The Sox are not built on a 10-12 year plan. They have a lot of high value contracts that are not over performing their value (David Price, Dustin Pedroia, etc.).
Almost all of their best players have contracts expiring after 2019 and 2020 and they are going to have to drop some payroll eventually. Their farm system is largely depleted of talent that is going to supplant the talent they have at the MLB level. Keeping Betts on his current deal allows the Red Sox to consider all possibilities including a partial rebuild after 2019. If Martinez leaves, Porcello leaves, Bogaerts leaves and Sale leaves, they could bring back an absolute haul for Mookie Betts, even with just 1 year left on the deal and inevitable free agency. They have to leave open this option, even if both Betts and Boston intend on a reunion after 2020. They will have to bid with everyone else.

J.D. Martinez

Here’s a name no one is speculating that they should be. J.D. Martinez stepped in right where Ortiz left off and anchored this lineup. He may not have Big Papi’s personality and swagger, but boy does he have his bat. Martinez was absolutely cheated by not being named #2 in the MVP voting. This guy looked late in the season like he could still make a bid for the triple crown and I think in and out was the best hitter in baseball in 2018. There’s an argument to be made he has been a top 3 hitter for years now. In 2017 he hit the ball hard an astounding 49% of the time and followed that up with a 44.9% mark this past year. Even more amazing, his soft contact rate went down from 14.0% to 10.9%! That’s a pretty significant drop considering how low it already was. His K/BB ratio continued to improve in 2018 (0.47 vs 0.41) and his K% was a career low for a full season at 22.5%.

Why this makes sense for J.D. Martinez: None of us can fight father time. Reworking his current deal allows him to make more money in 2019 and gets him security beyond 2021 when his current deal ends if he doesn’t opt-out (which he obviously will). If he can secure a 5/$145-150 million deal from the Red Sox, it’s in his best interest to take it. He will finally get paid at the level he deserves and secure his future among the highest paid players. Martinez has nowhere to go but plateau or down, sadly. I see no way that he can continue to improve as father time catches up with him. However, I said this year we should taper our expectations and not expect the show he put on in the desert in 2017. I was wrong then, and I could be wrong now. J.D. has never been wrong betting on himself and we all just watched what David Ortiz did in his career finale. Why can’t Martinez age like that too?

Why this makes sense for the Red Sox: There’s not much else to be said that hasn’t been said already. The offensive combination of stats Martinez has produced over the last 3 seasons are unlike anyone else in baseball. Martinez is the middle bat this lineup was missing desperately in 2017, following Ortiz’s departure. The Sox can pay now and feel good about a 5 year deal, or they can wait another year and still have to give Martinez at least a 5 year deal or watch him walk away. If Martinez is willing to sign for 5 years and the Red Sox don’t have to go 6 or 7 to bring Boras to the table, they would be foolish to not try to get this deal done.

Why I don’t think it will happen: Scott Boras. Boras is not known for letting his guys ink extensions this close to free agency. Not at Martinez’s pay grade. Boras always bets on himself and his ability to get his guys the right deal. However, this strategy has backfired in the past and Martinez’s last trip to free agency could bring Boras to the table early to talk. I just don’t see it.

Xander Bogaerts

Other then Rick Porcello, Chris Sale and J.D. Martinez, Xander Bogaerts is yet another player bound for free agency after 2019. The Red Sox know they are losing at least 1 or 2 of these 3, more then likely. Payroll limitations say it must be that way. While a bit of a slow riser with a lot of bumps along the way, Bogy solidified in 2018 that he is indeed among the best shortstops in Major League Baseball and he belongs right there in the discussion with Correa, Seager & Lindor. Bogaerts’ leadership has stepped up the last few seasons as well. He’s frequently going to the mound to talk with starters since Pedroia’s injuries and has shown some real leadership capabilities. He seems to be a very calming presence in the lineup and locker room and rarely looks over-matched by top starters anymore.

Why this makes sense for Xander Bogaerts: Bogaerts has had a tough start to his career. Inconsistency and injuries plagued his early years. Every time you thought he was possibly the best shortstop in baseball, an injury seemed to halt it. The wrist injury was particularly draining on his production for awhile. Bogaerts may be willing to overrule Scott Boras and stay in Boston. Of all the players that get media attention in Boston, Bogy somehow seems to fade to the background and miss out on a lot of the spectacle. He seems very comfortable and the Sox have stuck with him through good times and bad. It will be interesting to see if Pedroia’s influence rubs off on Bogaerts.

Why this makes sense for the Red Sox: Simply put, it doesn’t. To bring Bogaerts back to the Red Sox with Boras would take a 7-8 year deal at $25 million annually and the Sox have better ways to spend those resources and too many resources tied up in too few players. Resigning Bogaerts and then letting Betts walk would alienate the fan base. I think Bogaerts will be the next Cano deal. He will always perform when healthy, but at a regressing level as he hits his 30s. Even if it did make sense:

Why I don’t think this will happen: Bogaerts’ agent is Scott Boras. He didn’t have Bogaerts wait this long to sign an extension.

Eduardo Rodriguez

Eduardo Rodriguez quietly put together his best numbers this past season. His 10+ K/9 was the best of his career as a starter. His 129 innings pitched were his second most as a starter. His 3.12 ERA was not fully supported by FIP and xFIP, showing that he had some great defense behind him, but the numbers are generally authentic given his increased K/9 and decreased walk rates. He looks like a guy primed to break and has for years. Injuries to his knee have forced him to miss chunks of time but he has seemed to come back pretty strong. The stuff is all there. If he can stay on the field and in the strike zone consistently, make no mistake Rodriguez has #1/#2 type talent.

Why this makes sense for Eduardo Rodriguez: Much like Bogaerts, Rodriguez has been humbled in his career by injuries and inconsistencies. Taking security now makes sense as the Red Sox have been loyal to Rodriguez and always given him chance after chance to prove he’s the guy they think he is. In 2018 and for stretches of years prior, he has rewarded their patience in key moments. I think he knows everyone around him in Boston wants him to become the pitcher he wants to become and will help him get there.

Why this makes sense for the Red Sox: This is a great story of a guy coming up. The Red Sox were eyeing Rodriguez for about a full year before they traded for him and he has for the most part delivered. However, it hasn’t been without quite a few bumps. Dustin Pedroia gave him quite an earful during a 13-7 loss to the Rays and he forever has frustrated managers who can’t seem to find a way to get the ace they see to perform like an ace. The injuries and bumps in the road put the Sox at a strong point of leverage in negotiations and if they think Rodriguez can live up to his expectations eventually, locking up another power lefty behind Price for the next few years is not a bad move.

Why I don’t think this will happen: This is plausible to me. Putting some cost certainty on Rodriguez given he’s already in his second year of arbitration eligibility makes some sense. If you can sign him to a 5 year deal and keep a pitcher with some cost control who can slot in the middle of your rotation comfortably, that would make some sense. Even this seems a stretch though, because Rodriguez has yet to put together a full season. When he does, it’s likely going to look really good and he might get paid for it. However, I think the Sox brass would like to see him prove it before handing out a long-term pact, even if it costs them a few dollars in the future.

Andrew Benintendi

This is the part you’ve been waiting for right? And with good reason. What would it take to buy out Andrew Benintendi’s arbitration years and get him locked up at a controlled cost? And would he be willing to put some free agent years on the table? Andrew Benintendi is team controlled in 2019. In 2020, his projected arbitration costs will be close to Mookie Betts $10.5 million, likely coming in right around $10 million. 2021 in his second year of arbitration, Benintendi could get closer to $15 million and $20 million in 2022 (his final year of arbitration). So to buy out those years, the Sox would likely have to spend a little more on the team controlled year, but could cut some cost in arbitration potential for cost certainty and security for Benintendi. When it’s all said and done, the deal that makes sense here is 5 years and $65-70 million.

Why this makes sense for Andrew Benintendi: This makes sense for Benintendi because a 5 year deal allows him to hit the free agent market at 29 and seek a 7+ year pact at 29. It values his arbitration years around the 10/15/20 marks mentioned above while throwing in 20-25 million for his first free agent year. The Sox are taking on a good chunk of risk with this pact, betting on Benintendi continuing to get better and one day being deserving of a 20+ million salary. For Benintendi, if injuries or uncertainties derail his career, he will have protected his family and his future with such a significant deal. Asking the Sox to pony up 9 figures with his talent isn’t out of the question, but it is not reasonable. The Sox still have a year of team control left and that has to be taken into consideration.

Why this makes sense for the Red Sox: There is no rush to sign Benintendi. He’s controlled for 4 more years. However, with their payroll decisions looming, cost certainty is going to become more important. The Red Sox hope that Benintendi becomes a superstar caliber player (he’s already a very, very good one) and if he does, getting him for that extra free agent year at a value of $25 million may be a bargain. However:

Why I don’t think this will happen: As I’ve mentioned with many others, there’s no real reason for the Red Sox to do this deal unless they plan to keep spending at a rate of $250 million per season (which they said isn’t going to happen). While the deal makes complete sense, in theory, independent of other deals this one doesn’t make sense to me. There’s too many other areas where resources will have to be allocated in 2019 and 2020 to tie them up in someone that could have a down year and never hit those arbitration paydays.

Who makes the most sense?

There are some honorable mentions here. The Red Sox could look to lock up Chris Sale. They could extend a contract extension to Jackie Bradley, Jr., using his lack of a trade market to keep him from free agency. However, I don’t think any of these deals make sense. More than likely, the Red Sox are kicking the tires with Mookie Betts to get an idea of what his thoughts are and if they could find a common ground. It would be shocking to see it lead anywhere though. If an extension is reached, I think the most likely suspect is Eduardo Rodriguez on a team friendly pact. The Sox could definitely use some future cost certainty at starting pitcher behind Price & Eovaldi and locking up Rodriguez for 4-5 years alongside those two seems the most likely option to me. My second choice would be Martinez and Boras not risking another difficult winter next year and solidifying a longer pact. What do you think?

By | 2019-01-08T12:29:20-04:00 January 8th, 2019|Player News, Team News|0 Comments

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