The Sunday Baseball Column: How committing to a Mookie Betts deal might work

By WEEI 93.7

The Red Sox have been clearly willing to go down what can be an uncomfortable path, that of giving one player the kind of annual average salary that might make up a small market team's entire payroll. Offers along those lines have been made to Mookie Betts.

As good of a player as Betts is, such a maneuver is one of the most difficult decisions an organization will have to make.

Last offseason three general managers were faced with similar situations, getting the go-ahead from their respective ownership groups to allocate history-making money to one foundational player. For Philadelphia's Matt Klentak, San Diego's A.J. Preller and Billy Eppler of the Angels this was the kind of moment that can make-or-break an organization and a baseball operations chief's tenure in the big seat.

So when the deals were done for Bryce Harper (13 years, $330 million), Manny Machado (10 years, $300 million) and Mike Trout (12 years, $426 million) a specific thought process -- one which was hatched years before the actual signings -- had offered the base for each contract. Talking to at the GM Meetings, the three executives explained the ins and outs when it came to making this same sort of decision the Red Sox are currently staring at:


"I would be willing to bet it’s different for every team because it’s obviously very dependent on your own individual organization and the circumstance. For us signing Harper, for example, we viewed it as a couple of things taking into consideration. One was the competitive timeline of our major league team which we still feel is heading in the right direction. Two is the relative youth of the player. Harper was entering his Age 26 season. Thirteen years is a long time but among those years are a lot of prime years. There is a lot that goes into it. You want to make sure your market and your revenues can support fielding a team around that player. I think if you have one marquee superstar controlling too high of your payroll that can be a little bit of a challenge. Maybe not for everybody. But those are the things you want to think through. Also how that player is going to fit in that market. If you’re going to make that kind of commitment to that player, there are enough challenges in baseball already you would like to make sure you’re eliminating some of them if you can just by doing your due diligence of the player and his makeup and how he would potentially fit on your club. Even having said that anytime you’re signing a player to a guaranteed contract you know there are some risks. You know over the course of a player’s career there are likely going to be injuries, and there are likely going to be good years and bad years. You just have to bake that into your decision-making process."


"Each situation is a little bit different. For us, with the last offseason with Manny, the farm system allows us to have some of those conversations. You talk about a percentage of payrolls, it depends on where you’re coming from. When you’re coming from a lower base it gives you the flexibility to consider somebody like that. We’re projecting we’re going to have some of those players in those 0-3 years and producing. I think all of that factors in. You understand you have to put a whole team around a player, so it wasn’t just about Manny Machado. You look up and you have a (Fernando) Tatis or a (Chris) Paddack and more guys who are coming up through the system who are going to be with us during a six or seven-year period with some type of control and some type of salary certainty.

"Manny asked a lot about (prospects). We sat down with myself, his wife and Manny in Miami and we talked for five or six hours. That was a big part of his conversation. His questions to us were asking about the big picture, the plan, the goal. His agent Dan Lozano also represents Fernando Tatis and he had met him at the futures game so he was aware of a few of those guys. Danny also represented Logan Allen. So he was aware of a few of those guys. We wanted to paint the picture that this wasn’t going to be just himself and a bunch of unknown players. We believe in these guys. We believe we’re also going to have the ability to add payroll over the next few years which ownership was committed to. That was all part of the conversations an the process of recruiting Manny."


"How does a player contribute to a team. Availability and productivity, right? If he’s available, taking innings and taking plate appearances, what have you, that’s good. That helps him contribute. And then productivity. How good is he when you’re giving him those things. When you’re giving him those innings and those plate appearances. Looking at it from that vantage point, somebody who can be available, that’s part of the player’s contribution and the player’s value.

"We weren’t going to build by trading Kole (Calhoun), trading (Garrett) Richards, trading (Andrew) Heaney, trading (Tyler) Skaggs. We weren’t going to do that. That wasn’t going to be the game-plan. That wasn’t what the Angels represented. That wasn’t what the brand represented. That also would have been fair to our fans. It wouldn’t have been fair to Mike. It wouldn’t have been fair to Arte. But we knew it was going to take a while to build a farm system. Players at the top of the farm system and emerging in the major leagues, they carry a lot of value with other clubs. You look at prospect value and financial capital. I think it opens ourselves up to a lot more possibilities than we may have had if we would have traded those players a couple of years back when they were in A Ball. Now they’re starting to blossom and get some national recognition or if we would have signed multi-year deals, which would have blocked having financial maneuverability. I look at us being more flexible and armed than the last three or four years."

"When we went through this in spring training Mike mentioned some of our prospects by name in his press conference. If I was one of those names mentioned that would be a pretty cool thing. I think he felt there was going to be reinforcement with that group and that gave him confidence where the organization is headed in that moment and time. What we do is look at how this player would expect to perform over the life of the contract, over particular segments of the contract. If you look at payrolls year by year … We would look at who was coming up in the system, what our flexibility could be, what that player would be producing for us. The baseball operations chair is just one viewpoint. There is a business viewpoint. There is an ownership viewpoint. When a player is drafted, developed and signed by an organization … We are his baseball home. Everybody kept bring up East Coast, East Coast, East Coast. That’s great. That’s where he goes and watches his football games, does his hunting and those things. But we’re his baseball home, that’s it."

So, how does all of this translate for the Betts situation?

One thing that jumps out is how the farm system impacts this whole equation. If Betts takes the approach of these other players and prioritizes the sustainability of the Red Sox' roster for years to come that might not necessarily be a good thing. It is universally believed that the Sox' best hope at finding impact young talent resides in the lower levels of the minors, leading to more uncertainty.

The ability of the Red Sox to keep their payroll manageable while locking in talent around Betts is also somewhat of a mystery. Xander Bogaerts can opt-out of his current deal and there is a reason the Red Sox want to lock up Rafael Devers to an extension.

Between financial flexibility and prospect capital, Philadelphia, San Diego and Los Angeles call could claim more sustainable blueprints than what Betts would be buying into. It's just another piece of what figures to be perhaps the Red Sox' most important offseason puzzle.


By now you are familiar with the story written by The Athletic's Evan Drellich and Ken Rosenthal regarding the Astros' alleged use of electronic sign stealing in 2017. The concern in baseball is that this was an example of how technology can be -- and has been -- leveraged in ways that should make everyone in the game uncomfortable.

But while the focus is rightfully on what the Astros might have done in 2017, one strategy employed by the Red Sox the following year offered a clue to how such maneuvering was being viewed throughout baseball.

During a June series in 2018 in Houston it was noticeable that both the Astros and Red Sox were using multiple sets of signs with nobody on base. When asked why after the series' second game catcher Christian Vazquez told, "Because there are cheaters out there."

As it turned out, the Red Sox had suspected teams were using electronic (or other) methods -- beyond just relaying info from runners on second base -- since early in the season, having started the strategy of multiple signs with nobody on during a late-April series in Toronto.

"We talked about it spring training, being smart about things," said then-pitching coach Dana LeVangie. "We didn’t (execute the strategy at the start of the season). We probably should have, but we didn’t. We’re just trying to eliminate that one big hit, which could be a three-run home run. If they’re stealing signs or whatever, we’re ahead of it."

Something to think about as we wait for the fallout from The Athletic's report.


So, this is what I submitted for the Top 10 in the American League MVP voting: 1. Alex Bregman, 2. Mike Trout, 3. Xander Bogaerts, 4. Marcus Semien, 5. DJ LeMahieu, 6. Rafael Devers, 7. Mookie Betts, 8. Matt Chapman, 9. George Springer, 10. Nelson Cruz.

While some of the picks weren’t in line with the consensus Top 10, the disparity was in line with the majority of other voters. The two biggest debates from my vantage point? I was the only one who voted Bogaerts as high as No. 3 (where Semien finished) and some had a hard time slotting in Devers before Betts.

On further review … I stand by my order of preference.

Semien was a WAR (Wins Above Replacement) darling, coming in at 7.6 compared to Bogaerts’ 6.8. He was considered a better defender at shortstop and played in all 162 regular-season games. But when it comes to impacting games, It is hard for me to pick the Oakland star over Bogaerts. It’s close, but …

Bogaerts:  155 games, .309 batting average, 110 runs, 190 hits, 33 HR, 117 RBI, .939 OPS, 85 XBH, 11 GW RBI, 341 total bases.

Semien: 162 games, .285 batting average, 123 runs, 187 hits, 33 HR, 92 RBI, .892 OPS, 83 XBH, 5 GW RBI, 343 total bases.

As for Devers over Betts, I also look at how one player impacted games more than the other. Sorry, but a hit is more important than a walk before more positive things can happen when you come away with the former instead of the latter. And while Betts’ 6.6 WAR is .7 better than Devers, and the right fielder is certainly a more impactful defender, the offensive disparity is hard to get past.

Devers: 156 games, .311 batting average, 129 runs, 201 hits, 32 HR, 115 RBI, .916 OPS, 90 XBH, 16 GW RBI, 359 total bases.

Betts: 150 games, .295 batting average, 135 runs, 176 hits, 29 HR, 80 RBI, .916 OPS, 74 XBH, 11 GW RBI, 313 total bases.


Cherington deserved another chance, and he's getting one. Four-plus years after being let go by the Red Sox he has landed as the chief baseball operations guy for the Pirates.

While Cherington was with the Red Sox there were two primary knocks on how he managed: 1. He was too methodical; 2. There were a couple of bad free agent signings.

Taking the second one first, in fairness to Cherington the power structure when Hanley Ramirez and Pablo Sandoval were brought in -- along with the decision regarding Jon Lester -- was confusing, with few able to identify if the decisions were being pushed by ownership, then-President Larry Lucchino or Cherington and his group.

As for Cherington's methodical nature, it sometimes led to holding on to prospects that probably shouldn't have been prioritized. But there are a few cases -- as pointed out in Alex Speier's excellent book "Homegrown" -- where the former GM saved the day with his decisions to not deal.

The one that jumps out is a reluctance to trade Mookie Betts to Milwaukee during the 2013 season for reliever Francisco Rodriguez. Or include Betts in the three-way trade that ultimately reeled in Jake Peavy. Considering we were talking about a diminutive minor-league second baseman who played a position the Red Sox were seemingly set at for years to come, dealing Betts at the time wouldn't have raised many eyebrows. But this where the ability to fight off the allure of the here and the now can't be understated.

It was an approach put on display again when Cole Hamels was on the market, with Cherington unwilling to discuss either Betts or Bogaerts with the Phillies.

The balance of falling in love with the prospects a team drafts and develops and knowing when to let go was a topic recently broached by Red Sox Chief Baseball Officer Chaim Bloom on the Bradfo Sho podcast:

"Like it or not, these decisions will find you. And you’re much better off recognizing that up-front and recognizing if you allude one today it might come back some other form tomorrow or might come back in a form you can’t control or you missed an opportunity or you were late with something. … I think the best way to think of it as you want to have a good process with everything you do as much as you can. It will never be perfect and shouldn’t be perfect. We should always want to improve it. But if you believe in your process I think you have a way of making these decisions a little more calmly and rationally. You’re always going to be gritting your teeth a little bit with a lot of them. But you can feel confident that you’re accessing everything the right way and doing what’s best for the future of the organization.

"To some degree, you’re going to (overvalue your prospects). As much as you try and control for it there is a lot of pride for the players you develop yourself and there should be. … I do think it’s a factor with every club and it’s basically impossible to fully detach from it."


- Word out of the GM Meetings was that the J.D. Martinez decision to opt-in really wasn't that difficult a decision for the Red Sox' slugger, hardly coming down to the wire.

- A small lunch place next to the pool at the Omni Scottsdale offered an interesting sight Monday. With the exception of a few patrons, the list of customers was made up of current and former Red Sox executives. At one table was the team's current group -- Chaim Bloom, Brian O'Halloran, Eddie Romero, Zack Scott and Raquel Ferriera. Then there was the Arizona contingent consisting of Mike Hazen, Jared Porter and Ariel Sawdaye. Also, there was Jared Banner and Allard Baird of the Mets, with the Cubs' Theo Epstein and Jason McLeod trickling in. (Paul Epsten, Theo's brother, was also in attendance for good measure.) There was, however, no sign of Dave Dombrowski.

- Those in the Red Sox' front office would have liked Tony La Russa to stay, and he certainly had the opportunity to do so. But the question that led La Russa to Anaheim involved what exactly the Hall of Famer's role with the Red Sox would be without his longtime friend Dombrowski running the show.