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Shaun’s GM simulation breakdown

New York Yankees v Boston Red Sox Photo by Rich Gagnon/Getty Images

Every year I play the utility role in our SB Nation general manager simulation. I’ve done the Marlins, the Pirates, and the Orioles over the past few winters. This year I ended up taking over the Red Sox.

I didn’t have an objective necessarily when I started, but I knew that I wanted to try to do two things: extend the Red Sox window and try to drop payroll a bit. If the latter wasn’t accomplishable, I wanted the money to be spent efficiently if it were going to be spent.

You are going to read these few words a lot in this write up: I actually like... Many of the guys I traded I do like, but value is value, and if you can get better value elsewhere, then you like that more.

I was given a payroll of ~$244M, which means if with the current roster I could add another big name. Initially, I set my sights on Manny Machado, provided the bidding didn’t get too outrageous (spoiler: it did). But the Red Sox have Rafael Devers and Xander Bogaerts. Devers is controlled for several more years, at a cheap price too. Bogaerts is better but he’s much more expensive and is a pending free agent after 2019. My initial idea was to trade Xander Bogaerts for some cost controlled pitching, then sign Machado.

We actually had a deal in place with the Padres to acquire Bogaerts (a note: extensions are not allowed in this sim, but I’d assume the Padres would have acquired and extended him in theory). The trade was Xander for:

Michel Baez

Cal Quantrill

Logan Allen (returning to the Red Sox)

Jacob Nix

Robbie Erlin

That would have been a boatload of pitching, with Baez and Quantrill as the two main pieces. That seemed like a damn good deal to me for six months of Xander Bogaerts, no matter how good he is. However, the Padres pulled deal overnight after they worked out one to acquire Addison Russell.

But why do we fall? So we can learn to pick ourselves back up...

So on to the moves:

Red Sox exercise Chris Sale’s 2019 option

No brainer...

Red Sox trade David Price to the Giants for John Gavin

So I was actually surprised how easily and quickly this came together. The Giants came asking about Price, knowing they could take on his contract. We went back-and-forth on some names for them to send back (I asked about Tyler Beede as the flyer) and we settled on John Gavin.

Gavin isn’t a great prospect by any means, but that isn’t the requisite return for ridding Boston of the entirety of Price’s deal.Price was about a 3-win drop in expected record, so while the performance cost was steep, the money saved allowed those three wins to be found a bit cheaper.

White Sox trade Danny Dopico to Red Sox for Rusney Castillo and Bobby Dalbec

Another unloading of a hefty burden, the White Sox seemed pretty excited to get Castillo, reasoning that he just needed a change of scenery, and worst case is they have to eat $25M.

I wasn’t expecting much back for the salary dump, and while Dopico has a plus to double-plus fastball, he isn’t much of a prospect. But still I reasoned, I’d rather have the money to spend and Dopico than Rusney Castillo.

I actually like Dalbec and think he’s a bit underrated. I fought as much as I could to keep him, but the Giants made it clear they wanted him or better (like Chavis or Groome). His power is real, and so is his arm, and he’s hit everywhere...still I don’t think he’s someone the Red Sox would miss in the alternate reality years down the alternate reality road.

Red Sox sign Shelby Miller to a 2 year, $6 million deal with incentives

Okay so now I’ve cleared some payroll but I needed pitching. Everyone I inquired on was just too expensive it seemed.

We tried for JA Happ but he went for 3/$42M and that was a bit more than we wanted to pay a guy his age.

Dallas Keuchel we never offered on, but he went for 4/$88M and we’d be out on topping that.

We tried to try on Clayton Kershaw but he signed just before we could make a formal offer. He went for 4/$130M. I don’t know if we would have tried to even top that, but I expect not, especially since we were trying to spend significant capital on Machado.

We loved Patrick Corbin but were quickly out of the race on him when he started getting upwards of $100M+ (he went for 6/$153M). Same for Nathan Eovaldi, who ultimately ended up getting 6/$90M.

So ultimately, we ended up narrowing our list down to Shelby Miller, a name that might bring a scrunch to your face, but would you be surprised if I told you he was projected for 1.4 wins in 2019? We actually plan on using him in a bullpen/swingman role like Eovaldi or Andrew Miller, so his stuff could play up a bit. He’s also is “only” 28 years old.

The actual deal itself:

2019: $2M + $500K for every 20 innings and $1M at 100 IP

2020: $4M + $500K for every 20 innings and $2M at 100 IP and $3M for 200 IP combined in ‘19 and ‘20 (so $6M if he reaches 100 IP in both years)

We had a pretty cheap contract on him that could be scraped easily if the role didn’t work out. Using him in that swingman role, it’s possible but unlikely he reaches enough innings to satisfy the $1M, $2M, and $3M incentive marks, but we included those in there in case we do end up starting him.

Red Sox non-tender Steven Wright and Brandon Workman

I knew I wanted to upgrade the bullpen, and Wright/Workman were two guys I wasn’t a fan of and both were making triple the minimum salary. While I wasn’t looking for guys making that, I thought I could spend ~$3M better on one guy than $1.5M on each of them.

Red Sox sign Wilson Ramos to a 2 year, $20 million deal with a club option

Another area I wanted to upgrade, as the Red Sox had the worst catching staff in baseball (-2.1 fWAR and a 44 wRC+). I thought I’d have to win a bidding war for Ramos, but I was surprised I didn’t really.

He isn’t an exciting name but he’s projected for three wins next year, the sixth best for a catcher. Yes, he has some injury concerns, but he went for pretty dang cheap for his expected production and he was dang good last year.

We actually played Ramos and his agent a bit here. We initially offered him a straight up 2/$22M deal and his agent said it was a good offer but they’d keep in touch. After a bit, the agent followed up if that deal was on the table. I knew that meant they didn’t have much interest elsewhere and I said we were a bit “softer” on him now, and countered with 2/$18M and a club option.

2019: $7M

2020: $11M

2021: $10M or $2M buyout

Ultimately he took that offer. We were happy to have him both on cheaper terms than the original 2/$22M but also to get a 2021 team option for less than his 2020 salary.

Red Sox non-tender Sandy Leon

With the addition of Ramos, we didn’t need Leon given that he was projected for almost $2.5M in arbitration and we didn’t want to eat the money of Christian Vazquez’s deal (he’s better as well).

Red Sox trade Mike Shawaryn to the Marlins for Drew Steckenrider

Back to trying to boost the bullpen. I’m sure of you guys here like Shawaryn, and he was actually asked about a bunch by other teams. It’s not that I don’t like him necessarily, but I like Steckenrider more. There is some reliever risk in Shawaryn and his upside, even if he sticks in the rotation, isn’t much more than Steckenrider’s current profile in the bullpen.

Steckenrider is coming off a back-to-back half win seasons, has a career 3.44 FIP, and 30% strikeout rate. There are some walks that go alongside side those strikeouts (a 10% rate) but he was cheap, under control for awhile, and youngish.

*A Marlins note: We tried to get JT Realmuto, we really did, but even offering Groome + Chavis and others, they had better offers (ended up going to the Astros for Kyle Tucker, Corbin Martin, Francis Martes, and Abraham Toro-Hernandez).

Twins send Taylor Rogers and Luis Arreaz to the Red Sox for Blake Swihart

Looking for even more bullpen help, Rogers jumped out to me. I noticed our pen was getting a little righty heavy, so I wanted to find a young, cheap guy who could destroy lefties. Rogers is it, and more.

This deal actually took a bit to hammer out. We exchanged names early on, but the Twins couldn’t make their payroll work for the move we talked about and they only had one other left handed reliever left other than Rogers. We eventually circled back to discussions after he had mentioned about Swihart.

Last year he put up two wins as a reliever, one of only about fifteen in baseball to do so. He also has a career .228 wOBA against him against left handed batters and was still decent enough against righties (.314 wOBA against).

I actually figured we could do a one-for-one swap of Rogers and Swihart, but the Twins offered to add more after a few exchanges. We asked for Rogers and Lamonte Wade (an MLB ready 4th OF type) but they were counting on Wade in 2019, so they countered back with Arraez.

I have a thing for undersized 2B who can hit, and while Arraez is pretty devoid of power, he makes a ton of contact, goes the other way, and is an okay 2B. Rogers was the core piece obviously, but Arraez was a good kicker for me.

Manny Machado saga update:

We started off with 11 years and $370M, with opt outs after 2020, 2021, and 2022, expecting Machado to likely take the 2020 opt out. It turns out at that point, Machado was already at 12/$400M with another team. We didn’t like that but Machado is a special talent, so we gritted our teeth and upped our offer to 12/$410M (what’s an extra $3M a year...) with the same opt outs.

After a bit, Machado’s agent asked for everyone’s final offer and a reason why he should sign with your team. I stood firm at my offer of 12/$410M and replied:

“He will join one of the most prestigious franchises in sports, defending World Series champions, and will have his choice to play SS or 3B. He’ll also be joining an American League team, where he has positional flexibility to DH.

We are also giving him the ability to opt out three times in his deal, as early as after 2020, given him several chances to maximize his earnings.”

Ultimately that wasn’t convincing enough, and he ended up going to the Phillies for 11 years and $433M, including a full no trade clause (I will never do that) and an opt out after year four.

Needless to say, we were pushing it at 12/$410M, so a higher total contract and shorter length definitely wasn’t going to work for us.

Rockies trade German Marquez and Grant Lavigne to the Red Sox for Rafael Devers, Jay Groome, and Alex Scherff

I wouldn’t say unfortunately, but it was kind of bad timing that the Machado signing came shortly after the Devers trade. We had to make a choice, and while I thought our offer on Machado was extremely strong and going to be the winner, we knew we had to pull the trigger on the Devers offer we had with the Rockies before they took it off the table.

Let me say again, I like Devers. I think eventually he’ll be an above average player. He’s only 22 for God’s sake. But I also knew the Red Sox might not be better off waiting for that day to come (if it ever does). Devers has a career 97 wRC+ over 730 career PA in the majors. A small sample size to be sure. I didn’t like trading him (or Groome) but I liked what I got back.

With Groome, I am a big fan and thought the Red Sox got a good pick when he fell to them after some off field concerns and signability questions. That of course was three drafts ago and now we’ve added a Tommy John on top of that. Groome may be the Red Sox top prospect, or close, but that’s due to attrition of others and not because he really has boosted his stock.

Scherff has good stuff but with the injuries and higher than average reliever risk, I was okay with him as the kicker.

In return, we got German Marquez, who I was wildly excited to get. He’s just a little older than Devers and just put up a 4.5 win season while pitching half his games at Coors Field (notice the 3.10 xFIP being a bit lower than his 3.40 FIP). He’s projected for four wins next year and could be better if he played less games in Colorado.

Marquez is also controlled for another four years, with one more at the league minimum. This was the controlled young pitcher I was looking for.

As the kicker on their end, I asked about Garrett Hampson but was immediately turned down, which was understandable. He was going to get some time with the big league club next year and looked promising. Then I reached for Ryan Vilade (who I liked a lot in the 2017 draft) but they countered with Grant Lavigne.

Lavigne isn’t an excellent prospect, but he walked more than he struck out last year, just turned 19, has plus raw power, and could project for an average hit tool. Definite sleeper in this alternate Red Sox farm system.

Red Sox sign Mike Moustakas to a 2 year, $25 million deal with a $12 million club option and $3 million buyout

After missing out on Machado and trading away Devers, we obviously needed a third baseman. I figured Moustakas would go for a little more than I was comfortable with, but I inquired just to be sure. I guess I read his market wrong because his interest was so low that Moustakas was talking to teams in Japan.

So I had to reset my expectations. I didn’t want to offer him a huge deal to sway him away from Japan, but given his softness was more than I expected, I offered terms we thought were a steal that he would still entertain. We sent his agent:

2019: $12,500,000

2020: $12,500,000

2021: $12,000,000 team option with a $3M buyout

Moustakas was guaranteed 2/$28M with a potential for 3/$37M. Even if it ended up as the latter terms, we were fine with that and it would be of our choosing given the team option.

Moustakas might not be a sexy name but he just put up a 2.4 win season and is projected for nearly three wins in 2019. Even if he has the same output as 2018, he’d be worth $22M alone. If he matched his projection, he’d pay for his entire deal in one season.

I’ve written a ton on Moustakas and his plate approach. He once tried to go opposite field more and it didn’t worked, so he ended up just going back to pulling the ball and his power came back. Then he started to swing more, particularly inside pitches, and he set the club record for home runs.

I immediately thought he’d be a good fit for the Red Sox, as his pull heavy approach from the left side would work wonders at Fenway.

I probably could have gotten Moustakas at a bit lower price, but given that I already thought he was at a big discount, I didn’t want to push my luck.

Red Sox trade Rick Porcello and Darwinzon Hernandez to the Phillies for Carlos Santana and Nick Pivetta

I was expecting to roll with Porcello and the rest of the rotation but the Phillies came asking about Bogaerts. We said that he wasn’t available given that we’d have to then rush to find a SS since we traded away Devers and didn’t sign Machado, and Moustakas definitely can’t play short.

He had mentioned about us taking Carlos Santana (likely due to the cost of signing Machado) and his semi-lofty contract, but I said we not only didn’t have a spot for him but he was also going against us trying to trim the expenses a bit. So he offered a swap for another bigger contract and said they’d trade Santana dand Pivetta for Porcello.

I was a bit surprised by this, and I had no problem keeping Porcello, who wasn’t that old, only had one year left, and was projected for a nice 2.5 wins in 2019. But then when they included Pivetta, I became immediately intrigued.

They had mention just a one-for-one Santana-for-Porcello but I reasoned that Porcello was the better asset given his age, performance, and contract. They agreed, so we had to expand the deal. After some back and forth and a few exchanges about Vince Velasquez over Pivetta, we settled on the above swap.

They requested Hernandez as the kicker, and I had no problem shipping the 40-command pitcher who was likely a reliever without standout stuff.

Pivetta continues my goal to add affordable young pitching, and while he isn’t Marquez, he’s as good as Porcello, has much longer control, and is considerably cheaper. It’s possible Pivetta doesn’t even make in his control years combined what Porcello is guaranteed in 2019. Pivetta is projected for 2.5 wins in 2019. Last year his FIP beat his ERA by a good bit for the second straight year, his strikeouts were up, his walks were down, has a 95+ fastball, and an above average curve.

Maybe I’m buying into Pivetta a bit much, but which would you rather have between he and Porcello.

Now Santana does bring a bit of a drag here. He becomes the third highest paid player on the team and is owed another $34M over the next few years. However he isn’t altogether useless. The old 130+ wRC+ Santana that also caught some games is gone, but he’s still an above average hitter and is projected for ~2 wins next year. While I might prefer Mitch Moreland for half the production at 1/3rd the cost, Santana’s remaining deal isn’t too large of a burden and he is good enough to man first everyday.

Royals trade Danny Duffy and $23.5 million to the Red Sox for Triston Casas and Nick Decker

I was still missing a bonafide starter that I felt comfortable with, so I went looking for guys that projected well and wouldn’t cost the moon to pay or acquire. I found it a bit in Duffy.

While he has had his injury history, Duffy has been very good when on, and to me represented at a minimum a very good swingman reliever who wasn’t owed crazy money. Even if he was “demoted” to the Andrew Miller-type role, he still had electric stuff that he could dominate there. I don’t think his injuries are going to get any better (particularly not when the shoulder comes barking) but that’s also why he was easy to acquire and the Royals were willing to kick in cash for.

His remaining salaries are:

2019: $15,200,000 with $6,000,000 from the Royals ($9.2M owed)

2020: $15,200,000 with $8,000,000 from the Royals ($7.2M owed)

2021: $15,500,000 with $9,500,000 from the Royals ($6M owed)

The Royals chipping in money means we were getting three years of Duffy for just north of $22M, just shy of half his guaranteed money. Duffy only needed to be worth ~2.5 wins total to break even. I think that’s doable, with room for a lot of upside if he goes back to being lights out.

Because the Royals were kicking in money, I couldn’t get Duffy for nothing. I really like Casas, and wanted the Royals to take him this past June at either 18th or 33rd overall (Red Sox nabbed him at 26th overall). The profile is a tough to reach when you are a 1B-only and Casas is a big boy who needs to projection on his hit tool, but he’s a good defender at 1B despite his size and has massive raw power. This was tough to give up, but the farm system exists to increase the value of the big league club either through those prospects panning out and playing for the MLB team or being trade pieces. I went with the latter, but I can wholly imagine regretting this.

The Royals also wanted Tanner Houck, who I would have preferred to move instead of Casas, but that would have been back-to-back first round picks they’d acquire, something I wasn’t willing to give up. Since they wouldn’t do Houck plus another and were adamant about getting Casas, we had to cough up Nick Decker. Decker is a nice all-around tools kinda guy, who could move up the org ladder quickly if he hits. I didn’t want to trade him but I weighed Duffy’s value and the probability of Decker having an impact, and took Duffy.

Pirates trade Nick Burdi to the Red Sox for Esteban Quiroz

This was a weird one. The Pirates asked about Quiroz at the very beginning of the sim and while I didn’t have that much interest in moving him, I said I’d get back to them later. Then they followed back up near the end of the simulation, and I looked at their remaining farm for a possible switch.

Quiroz fits the player I like a bit, but as high as some Red Sox people may be on him, his numbers and tools aren’t all that impressive. He might be underrated, he did just join (actual) pro ball, and he just hit .299/.413/.598 in AA...but he did it as a 26 year old. This was after beating up on Mexican League pitching for seven years. Maybe you want to make Jose Altuve comps, but a reminder that Altuve beat up on MILB pitching before he was old enough to drink, unlike Quiroz who reached AA at the same age as Altuve was when Altuve was putting up 7-win MVP seasons.

The one thing that worries me is Quiroz is projected for a 111 wRC+ next year, on par with guys like Lorenzo Cain and Starling Marte. Obviously the latter two have years of MLB experience, so their data is a bit more reliable, but there was definitely some risk in moving Quiroz.

In return, I got Nick Burdi back. Burdi has one of the best one-two pitches in baseball with a double-plus fastball and slider. He’s had injuries (including Tommy John) and his command is garbage at times, but he has the ceiling of a lights out closer and is MLB ready.

A note: Burdi I think still has rule 5 restrictions on him for two more months or so, so he has to be on the 25-man otherwise he has to go back to Minnesota. That would suck, losing an interesting guy like Quiroz for essentially nothing (also costing $25,000 to return Burdi to Minnesota), but Burdi won’t require a full season on the 25-man at least.

And that’s it for all the moves made. Some GMs like to sign guys to minor league deals, but I didn’t bother that this year, particularly with the flurry of moves I had already made, the happiness with my roster, and we end the simulation earlier than usual this year.

Here is the final roster and payroll:

I think the total 2019 projected WAR before I started was ~48 wins. After my moves, I’ve gotten it up to 56.3 wins. If that was accurate, that would put the 2019 Red Sox projected at ~104 wins. For reference, the Dodgers have the best projected 2019 record (based solely on WAR - not including their schedule) and they are projected for 96 wins.

Now you can probably lower down some of that due to playing time questions (like with Moreland and Santana), but I think overall this team is better than how it started.

But most importantly (I think) is that we finished almost $60M under the suggested payroll. This means that next year, the Red Sox could have $100M+ to spend on keeping guys like Mookie Betts, Xander Bogaerts, and Chris Sale without having to worry necessarily how to supplement them with guys in free agency given the control over guys like Marquez, Santana, Moustakas, Pivetta, Rogers, Ramos, etc... You retain Xander, Betts, and Sale after 2019 (not a given) and you can return basically the same team.

Projected lineup:

Needs a 4th outfielder (though I suppose Martinez works) probably and Moreland is nowhere to be found, but I think we can live with that. Also needs another left handed reliever other than Rogers. Bobby Poyner? Jalen Beeks?

The farm system took a hit with losing Groome, Dalbec, and Casas no doubt, but I was happy to retain Chavis.

Random notes

  • Atlanta and I talked a lot, specifically on Bogaerts and Devers. They were my go to for Bogaerts, knowing they had a ton of young and good pitching they could give up. Ultimately they got Trea Turner and shipped a bunch of pitching for Knizner + O’Neil of the Cardinals, and Jace Fry. I tried getting AJ Minter but didn’t want to give up Chavis to do so
  • JBJ had a ton of interest but nothing really ever gained traction
  • Cubs GM and I always have good discussions and talks. We’ve both been doing this sim for several years and we are both similarly minded. Didn’t find a match for anything this year, but we discussed various options (including Heyward - the money didn’t work on our end to make sense).
  • Needing another lights out lefty, I tried to pry Will Smith from the Giants but the ask was too much and we didn’t have what they wanted
  • The very first email we got was from the Mariners, asking about JBJ, wanting to put together an elite defensive outfield. They ended up acquiring Billy Hamilton and Jarrod Dyson, which fits their objective.
  • As mentioned, we tried to get Realmuto to now avail
  • The Mets and I discussed one of their controlled pitchers not named deGrom or Syndergaard. We talked about a Matz for Bogaerts swap briefly (I would have asked for more) but they moved on a deal for Matz. Wheeler also came up in discussion. We really like Seth Lugo as a lefty dominator, but we were too slow as they already included him in a deal for Victor Robles
  • Orioles and I talked about Bundy a few times but they never got far. I like Bundy, but I thought the ask was a bit too high. We tried getting Tanner Scott to fill our lefty role but couldn’t find the correct match on both ends
  • I obviously inquired on Felipe Velasquez (whose name I still can’t remember after he changed it from Rivero) from the Pirates, looking to replace Kimbrel, but the Pirates wanted to go for it this year/near future, so it was a non starter
  • We asked the Rangers about Mike Minor, both a lefty and an inexpensive starter, but we thought their ask was too high (one of Chavis or Groome)
  • I kicked the bucket on Kyle Crockett of the Reds as he’s killed lefties, but it stalled out
  • Rockies reached out early for Devers after they moved Arenado. We were happy to talk given our objective and the players we thought they could give us back. At one point they offered Riley Pint but as the world's biggest non-Riley Pint fan, I cut that out quick. We talked about Kyle Freeland and Anthony Senzatela, but I wanted Marquez above all.
  • We pinged the Phillies about Edubray Ramos and Seranthony Dominguez but they were holding onto those two if they weren’t blown away. We liked them but thought there was a better opportunity elsewhere for the likely price
  • White Sox and I had good discussions. We talked about Devers with them. They offered Giolito and plus. I’m a Giolito fan, but not enough of one to have him as the core piece for Devers.
  • We made a small 1/$3M offer with a team option to Justin Wilson but didn’t go anywhere. He ended up getting 2/$10M from the Cardinals
  • Yusei Kikuchi was a target as a lefty starter who was controlled and shouldn’t have been too expensive. We were too late on him as he signed before we inquired but he also went for much more than we would have been willing to pay (6/$65M)
  • We also targeted Trevor Rosenthal for bullpen help but he signed super early to a nice deal for Oakland (1/$6M with incentives)
  • Tested the waters on Andrew Miller, Yasmani Grandal, and Jeurys Familia; all were a bit too expensive for our liking
  • JA Happ was the kind of guy we like, as we thought he’d be an efficient money spend. He went for 3/$42M. Not something we wouldn’t have done, but we liked him more in the $30M range
  • We offered Eovaldi a 4-year, $50M deal with potential for 5/$60M:

2019: $10M

2020: $11M

2021: $12M

2022: $13M

2023: Team option for $14M with a $4M buyout

He went for 6/$90M to the Nationals. Well above what we were expecting and interested in

  • We had an offer for Clayton Kershaw written out (something like 4/$100M if I recall correctly) since we had a lot of budget left and wanted a light out starter to pair with Sale. He had already signed back with the Dodgers (just like in real life) by the time we got around to inquiring on it. Would have been interested to see where it went.