The Sunday Baseball Column: Did Red Sox miss the best window to trade Mookie Betts?

By WEEI 93.7

Holiday parties can always be a dangerous thing for baseball reporters

I remember during the Daisuke Matsuzaka saga leading into the 2007 season telling my wife I would not be accompanying her to a Christmas party because there was absolutely no desire to spend hours around the plates of cookies fending off questions about the Red Sox’ Mystery Man.

For doctors, it is answering questions about aches and pains. For those who cover the Red Sox, the holiday get-togethers are thick with a diagnosis of the luxury tax threshold.

This year the key question started at the Halloween candy giveaways and is running straight through the opening of the advent calendars: What do you think is going to happen to Mookie Betts?

So, part of the job is to have some sort of answer for this query. The problem is that when trying to nail the outcome of Betts’ future we are left to try and make sense of various pieces of this puzzle.

This what we know …

- Betts is digging in when it comes to what he views his value at. This, as he points out, is all business and zero emotion.

- The Red Sox have made Betts numerous contract extension offers, including what a proposed deal in spring training that would have put the outfielder among baseball’s elite when it comes to long-term, big-money contracts.

- Betts is slated to make around $27 million for 2020, with the 27-year-old heading into his last year of arbitration-eligibility. If traded, the other team would be taking on that money along with the uncertainty of just one more season of control.

- Betts’ on-field existence for the 2020 Red Sox is key considering what he continues to bring to the table. His presence on the payroll, however, is a problem considering the organizations’ desire to get its bottom line below $208 million.

- There aren’t any logical internal replacements for Betts in the Red Sox’ farm system.

When those facts, along with various comments over the past few seasons, have left us all guessing. But there is one aspect of the equation that was recently surfaced in a conversation with a baseball executive that stuck with me: “It’s hard to tell if Chaim would have traded him last season …”

Not a whole lot of merit was put into the idea of dealing Betts prior to this offseason, particularly leading up to last season’s trade deadline. When Aug. 1 rolled around the Sox’ leadoff hitter was just starting to get hit hot, hitting .373 with a 1.085 OPS in July. And the team was just two games out of a Wild Card berth.

But there were two quotes from team president Sam Kennedy when appearing on the Greg Hill Show immediately after the deadline that stuck with me:

1. “There were some discussions involving major league players and really rattling cages and shifting things around. I’m glad personally those didn’t happen because I believe in the guys we have right now.”

2. “No specific discussions about Mookie Betts or any other player. Just a general discussion, I think which is healthy. About a week before the deadline ownership, Dave and the team we sit down just kind of go through and say, ‘What are things looking like?’ I think it’s responsible for teams in our position that have the resources, we have great assets, we have great scouting and player development, we said to ourselves, ‘Let’s see what is out there on the market and would there be a willingness to listen to any deal?’ The honest answer to that is, ‘Yes.’ I think it would be irresponsible to not at least listen. Were there any substantive discussions, or really any discussions, that got to any type of ownership level on any of our elite players? No, there weren’t.”

They should have talked about a Betts deal, and one has to wonder if it was Bloom sitting in the big chair instead of Dombrowski if the conversations would have become whole lot more interesting.

While the aforementioned optimism of the time pushed aside the idea of actively shopping Betts it would have been the kind of approach Bloom’s former team, the Rays, made a living on. Granted, the stakes in Tampa Bay — along with the financial means — have always been night and day from Boston. But the whole goal is to stay out ahead of the kind of potentially uncomfortable existences the likes of which we find the Red Sox currently trying to manage.

For the Rays, their tough decision came at the 2014 trade deadline when they dealt David Price to Detroit in a three-way deal with a year still left on the pitcher’s contract. Facing having to pay Price what would be $19.75 million in the final year of control, Tampa Bay deemed it prudent to jump into the trade market a year before many might.

While this might not be an apples-to-apples comparison, the heart of the issue is identical: Figuring out if there is a realistic chance the player can be signed beyond their current commitment.

When last season’s trade deadline rolled around the Red Sox couldn’t have felt good about their chance to sign Betts to an extension considering his rebuffing of the team’s spring training offer. Yet they decided it was worth it to take the chance of getting progressively less in the trade market in exchange for having Betts continue to do his thing in a Red Sox uniform with probably some distant hope that financial common ground could be reached.

It’s not as if the Red Sox couldn’t get anything for Betts if they dealt him this offseason. (One could make the argument that Detroit got more in its Price deal with Toronto in 2015 then the Rays received a year before.) And it certainly doesn’t make sense to jump ship on the star outfielder if there is still hope, both in terms of winning games and agreeing to an extension.

But if Bloom was that chief baseball decision-maker for the Red Sox last July and knew what he knows now I do believe that cage-rattling Kennedy referenced would have been a lot louder.

So, what now? 

Let me — and the Red Sox —continue to think about it over some egg nog …


This was not the Thanksgiving week Brian Johnson was expecting.

After what he thought was going to be just another late-November workout Johnson’s phone gave the pitcher an unwelcome surprise: the Red Sox had put him on waivers.

“I didn’t expect it,” Johnson said by phone. “I was actually throwing at the time and I got back and my phone had a bunch of messages and my mom called a bunch of times. I didn’t know what was going on. It happens. It is what it is. You can only move on and try and keep working hard.

“It’s a business. It’s a game we play but it’s a business in the long run. They thought it was a good opportunity at that point and time to point me on waivers and get me back.”

The Red Sox still value Johnson but saw a window where the 28-year-old might not be claimed by another team and placed on their 40-man roster.

Despite Johnson’s breakout 2018 season, his injury-plagued 2019 left just enough of a mark in the world of baseball that teams — many of which had just maneuvered their 40-man rosters to make Hot Stove acquisitions — weren’t ready to make a 40-man commitment.

So now the Red Sox were able to open up a spot on their roster while keeping around Johnson, who has been implementing pieces of the highly-regarded Driveline throwing program in order to add a few MPHs to his fastball.

“Nothing changed. The only thing that changed is I’m not on the 40-man,” he said. I’m still going to go into spring training and fight for a job on the big league club.

“I feel great. I feel like I’m in a better spot going into this season. As weird as it sounds, with those injuries happening I did a lot of prep work so that stuff doesn’t happen again. This offseason we added other shoulder and elbow stuff, movements that could really help me out in the long run.

“In the grand scheme of things I’m just not on the 40-man. My goals don’t change. I have the same goal going into spring training, fighting for a job either in the bullpen or starting. Whatever happens, I’m going to keep working hard and let things happen.”


While the trend of teams prioritizing what they believe a player will do instead of leaning on their entire resume continued with the Drew Pomeranz deal with San Diego (4 years, $34 million), the signing also allows for an update on Anderson Espinoza.

Espinoza, you might remember, was the top Red Sox prospect the Padres secured in exchange for Pomeranz just prior to the 2016 non-waiver trade deadline. Heading into the 2016 season Espinoza was ranked as the No. 19 overall prospect by Baseball America despite being just 18 years old.

“He was always a name in the international scouting scene because of how easy he threw the baseball,” San Diego general manager A.J. Preller told regarding Espinoza, who had received a $1.8 million signing bonus from the Red Sox in 2014. “A young player who generated velocity, a really good athlete and threw strikes. He was a target knowing the Red Sox might be a team we lined up with because they had tremendous talent in their farm system and we felt like we had some big league assets they had interest in so he was always a target guy for our pro scouts.”

But the wait to find out exactly what San Diego has in Espinoza continues to be a long process.

The righty pitcher — who will be 22 years old in March — can be found at the Padres’ spring training complex rehabbing from a second Tommy John surgery. The last time he pitched in a minor league game was 2016.

“It’s been a tough few years,” noted Preller. “He worked really, really hard to get to the point where he could come back from Tommy John surgery. He was throwing free and easy in spring training, throwing the ball well. And then he was going in with what we thought as a group was more of a check-in with a little bout of soreness coming back from what we thought was a pretty natural progression from TJ. But it ended up being his second TJ.

“It’s not easy but the way he has handled things, with his makeup and his work ethic if somebody is going to do it he is going to be that guy to do it. You don’t want to see anybody get hurt, but especially with that special kind of ability.”


The first salvo when it came to the Sox figuring out a plan for their offseason was J.D. Martinez’s opt-in decision. Monday is Phase 2.

Teams have until 8 p.m. to inform arbitration-eligible players whether they will receive a contract offer from the club or if they will become free agents. 

Last year there were some difference-makers that hit the market thanks to their respective teams non-tendering them in last Nov. Avisail Garcia, Jonathan Schoop, and Mike Fiers (who ultimately re-signed with the A’s after his initial parting) all pivoted to be valuable contributors for postseason participants.

The two names the Red Sox’ followers should pay attention to are Jackie Bradley Jr. and Sandy Leon. 

Normally it would be a reach to think Bradley Jr. would be lumped in which non-tender candidates considering his obvious value to a winning team. But with the Red Sox desperate to find financial flexibility and the outfielder slated to make more than $10 million in arbitration it isn’t out of the realm of possibility. 

Leon — who is slated to play Winter Ball in Colombia starting this coming week — is more likely to be non-tendered considering his projected $2.8 million price tag in arbitration. With Christian Vazquez’s emergence, the number would be viewed as excessive for a player with the perceived role Leon will most likely be saddled with.

Other arbitration projections (per MLB Trade Rumors) Red Sox players are: Betts, $27.7 million; Brandon Workman, $3.4 million; Eduardo Rodriguez, $9.5 million; Matt Barnes, $3 million; Heath Hembree, $1.6 million; Andrew Benintendi, $4.9 million; Marco Hernandez, $700,000.