Going Deep

The long-dreaded, yet inevitable, happened for the Red Sox last week — David Ortiz announced he will retire at the end of the 2016 season. The news came as little surprise.

Ortiz is 40 years old and, after hitting his 500th home run in September, has pretty much reached every possible career milestone. But it does leave the Sox with questions beyond 2016. CSNNE.com’s Sean McAdam asked perhaps the biggest one — where will the Red Sox’s power come from in the post-Ortiz era? That answer seemed clear entering spring training last season. The Sox signed Hanley Ramirez to a four-year deal with the expectation that he would DH when Ortiz retires and, at least partially, fill the power-hitting void left by Big Papi. That seems unlikely now. Ramirez hit 10 home runs in April and finished with 19 for the year in what was a dreadful season both in the field and at the plate. The best-case scenario is that Ramirez is traded and never seen in a Red Sox uniform again. Let’s pretend that’s the case for a minute and leave him out of the mix. So who’s next? (Before considering this answer, let’s remember there’s really no replacing Ortiz, who hit 37 home runs with a .280 ISO — good for sixth in all of baseball — at 39 years old last season, especially when we’re looking at it from a power-hitting standpoint.)

Right now it’s Mookie Betts. Betts hit 18 home runs, eight of which came in the final 58 games of the season, and finished second among qualified Red Sox players with a .188 ISO. The now-23-year-old struggled at the plate over the first two months before turning it around considerably. The idea is that he is only going to get better. The next-best options are unproven minor leaguers. First there’s Sam Travis. He’s big, strong and has a long swing, but that’s yet to translate into power hitting (he posted a .136 ISO in 281 plate appearances with Double-A Portland). Then, of course, there’s Andrew Benintendi, whom the Sox drafted in the first round last June. His 239 plate appearances between Lowell and Greenville is a small sample size, but his production — a .250 ISO in Lowell and .230 in Greenville — was no joke. The problem, however, is that he may be years away from being major-league ready. Perhaps we’ll see Ortiz’s true value once he’s no longer in the lineup every day.

This offseason isn’t the first in which the Red Sox are in pursuit of an ace. But, as Michael Silverman of the Boston Herald points out, the way in which they expect to do it is unfamiliar territory for both the franchise and Dave Dombrowski. The last 20 years show that the Sox have been most successful when acquiring elite starting pitching via trade. It’s how they landed Pedro Martinez, Curt Schilling and Josh Beckett, all three of whom were instrumental to World Series championships. Their most recent ace, Jon Lester, was homegrown. This offseason, it appears the most likely way the Red Sox will land a No. 1 starter will be via free agency, whether they sign Johnny Cueto, Jordan Zimmerman, Zack Greinke or David Price. That’s something the modern Red Sox, and Dombroski, don’t normally do. The last top-of-the-rotation starter the Sox signed as a free agent was John Lackey. By then Lester was already in place as the No. 1. Other free-agent signings included Daisuke Matsuzaka and Matt Clement. Not exactly ace-quality right there.

Dombrowski’s Tiger teams were no different. Justin Verlander was homegrown, while Max Scherzer, Doug Fister and Price were all traded for. Why exactly are these such uncharted waters for the Sox and Dombrowski? Perhaps it’s the risk that comes with it. Just look at last season’s free-agent class. Scherzer signed with the Nationals for $210 million over seven years, while Jon Lester inked a six-year, $155 million deal with the Cubs. Both pitchers had solid first seasons with their new teams, but it’s how the coming years play out that’ll determine if the contracts were worth it. Meanwhile, James Shields had one of his worst statistical seasons in 2015 after signing a four-year, $75 million deal with the Padres. The Sox will need to spend Lester or even Scherzer money to land one of the top pitchers on the market. But first they need to determine who’s worth the risk.

Quick Hits

MassLive.com’s Christopher Smith makes the case for Greinke as the Red Sox’s top pitching target. Greinke had perhaps his best season in 2015, posting a 2.79 FIP, 7.6 WARP and finishing second in the NL Cy Young race. Last season wasn’t a fluke, either. Greinke may have occasionally flown under the radar pitching in the same rotation as Clayton Kershaw, but his three years with the Dodgers were some of his best, as he finished with a 2.97 FIP and 8.3 K/9 over a combined 602.2 innings. The righty has proven he can also do it in the American League, where he pitched with the Royals over the first seven seasons of his career and won a Cy Young in 2009. The one potential issue with Greinke is his battle with social anxiety disorder. But that’s a moot point given he how he handled the pressures of pitching in the Los Angeles market, as Chad Finn of Boston.com pointed out.

Don’t think we’re done talking about starting pitching just yet. The Boston Globe’s Alex Speier wrote an interesting piece on when the right time to trade a back-of-the-rotation starter is. The Red Sox certainly have a bevvy of those kind of pitchers. That will become more apparent if and when they acquire a No. 1 starter. That means someone will have to go. Speier explains why the Sox may be best served waiting until the middle of next season to strike a deal, citing the Cubs’ July 2013 acquisition of a little-known Jake Arrieta in exchange for Scott Feldman as a reason to be patient.  

Reliever Pat Light was one of three prospects added to the team’s 40-man roster last Friday. The 24-year-old righty has never been among the team’s top prospects since being drafted in 2012 and had an unspectacular 2015 season, especially in Triple-A where he posted a 4.28 FIP and an ugly 7.09 BB/9 in 26 relief appearances. But, as WEEI.com’s Rob Bradford writes, Light gives the Sox another hard-throwing arm out of the bullpen. Light’s fastball, which sits in the mid-to-upper 90s, is a commodity among pitchers that helped him average a 9.55 K/9 in Pawtucket. It appears to be an asset the Red Sox desire in their bullpen reconstruction after trading for Craig Kimbrel nearly two weeks ago. Unlike Kimbrel, of course, Light is young and unproven, just like Matt Barnes, who also lives and dies by a mid-90s fastball, was last season before finishing with a 5.23 FIP over 43 innings. That’s not to say Light will be like Barnes if he pitches in Boston next season. But you’ve been warned.

Not everyone was on board with the Kimbrel trade. The reason for that is the hefty batch of prospects the Sox were forced to give up in order to get him, most notably Manuel Margot and Javier Guerra. The Providence Journal’s Tim Britton analyzed what exactly the Red Sox lost in Margot and Guerra. Margot was one of the top-rated prospects in the organization last season. He’s a speedy, athletic outfielder with power potential, but his aggressiveness at the plate caught up with him in a disappointing stint in Double-A. The good news for Margot is he’s 21 years old and has time to improve his approach and reach his ceiling. Guerra was always touted for his defensive prowess at shortstop, but he was a pleasant surprise at the plate, where he finished with a .354 wOBA and 15 home runs in Low-A Greenville. The Red Sox, however, could afford to part ways with Guerra given Xander Bogaerts’ stranglehold on short for years to come.

It wouldn’t be Read Sox without a Roger Clemens reference, right? Rocket has an interesting place in Boston sports lore. He spent 13 stellar seasons as the team’s homegrown ace, but his most controversial moments came as a member of the Yankees with the rivalry at its peak. Then there was that whole steroids thing. If you’re under 25 (like me), you probably don’t like Clemens and see no place for him in the Hall of Fame. But if he were to be voted in, he’d don a Red Sox cap on his plaque — at least that’s what he said in a radio interview last week. Now that would be quite a sight.

Dave Roberts was named manager of the Dodgers on Monday. I bring this up as an excuse to relive the biggest stolen base in Red Sox history. Enjoy!

In everything I read, in everything I hear, the Red Sox seem to come up as a team who would be willing and able to spend big money this offseason as they attempt to change course of the S.S. Fenway. And my goal, at least for today, is not to try and prognosticate what the team will do, but rather what they can do. It’s a small difference, but perhaps an important one.

How much money do the Red Sox have, and what options does that give them?

According to the Cot’s Contracts page for the Boston Red Sox, the team had a payroll at the start of 2015 of approximately $184 million. That’s the highest payroll the team has ever fielded, and not by a small amount. Currently, according to Cot’s, the team also has about $153 million committed in salary for the 2016 season, before arbitration raises.

While I don’t believe the Sox’s payroll will hit the heights of the 2015 season, I do think the team will likely return to the top of the pack when it comes to total dollars spent, especially as new GM Dave Dombrowski is looking to make a sudden U-turn back to respectability. He’s said that the team payroll is “not going backwards.” My rough guess is $180 million in 2016, which is about a $5 million dip from the previous season, and leaves the team plenty of room to maneuver mid-season.

So … the Sox have about $153 million committed, and my guesstimates for who will stick in arbitration based on Matt Swartz’s arbitration projections (Tazawa, Kelly and Ross) run the bullpen bill up another $7 million. That leaves a grand total of $160 million (give or take a few bucks) committed, and leaves the Sox with about $20-30 million dollars to spend. Of course, my total payroll estimate could be conservative … there could be more cash available. Or everything we hear could be lies, and the team could scale back after the 2014-2015 offseason free agent fiascos. Who knows?

(Note: the team’s top three payroll earners for the next three seasons are Hanley Ramirez, Rick Porcello, and Pablo Sandoval. In 2016, they’ll earn approximately $60.4 million of the team’s projected $180 million payroll. One third of the payroll! 2015 WARP: -1.8! Whoops!)

So, what could the team do with all that scratch?

Option 1: Sign Zack Greinke. Maybe.

Greinke is, in my view, the best possible starting pitching option available on the free market … for the Boston Red Sox. I’m not convinced he’s a better starter than David Price over the next five years, but he’s right-handed (the team already has Ed, Henry, and Brian Johnson on staff), and I’m convinced he can adapt to Fenway Park due to the way he’s constantly made adjustments throughout his big-league career. Having said that, if you want to swap Price’s name for Greinke’s above, have at it.

Either name mentioned above is likely to command top dollar. Truthfully? I’m not sure that either player will settle for less than $25-$30 million per season. Both challenged for Cy Young awards this season and are still at or near their primes. Other teams will be looking to spend on pitching from New York to Los Angeles. Greinke has been paid $26 million in a single season before, and I doubt he’s looking to take a pay cut. David Price is two years younger and, arguably, better than Greinke.

This expensive option takes nearly every other cash-added option off the table, unless the Red Sox move salary some other way. While that’s an option, sure, keep in mind that the Red Sox’s big contracts are albatrosses, and would require the team to give up good talent to move them.

Option 2: Sign Multiple Lower-Tier Free Agents

Instead of buying the $80 steak from the white-glove steakhouse, perhaps the Sox are in the market for a couple of really tasty entrees at the bistro. To find these guys, I’m looking at the lower end of the qualifying-offer list: guys like Wei-Yin Chen. The team could use some offense as well, so perhaps a Chris Davis or a Dexter Fowler might fit in here. And then, of course, there are the various and sundry players at even a lower level-your Doug Fisters and David Freeses, your Jerry Blevinses. Blevii? Whatever.

This is certainly an option as well, though I have a bit of concern that if the team inks an Orioles combo platter of Chris Davis and Wei-Yin Chen, the team will be on the hook for a similar amount of money as they might be to an ace like Greinke or Price. Instead of having one (hopefully) transcendent star, they’d have two good-but-not-great players, and perhaps the same amount of risk.

Option 3: Buy A “Bad” Contract

Like the Sox, plenty of teams have contracts that they wish they could shed. With the free agent class looking like one of the best in years, I’m fairly certain that several teams would be over the moon to drop a pricey contract in the hopes that they could spend that money in a different area. Examples include the Padres’ pricey James Shields contract ($65 million over the next three seasons) or the Rockies’ pact with Carlos Gonzalez ($37 million over the next two seasons).

There are several performers who have contracts that don’t exactly track with their recent performances — as mentioned before, the Red Sox have three of them themselves — but the idea of paying top dollar for players who aren’t performing up to high expectations could be a bit much for a team already on the hook for “dead money” over the next few years.

But … while I’m here, can I throw out an interesting possibility? I love the idea of the Sox making a play for the Twins’ Joe Mauer, provided that Minnesota would eat about half of his contract. The Twins were the team that added Park, and seemingly have a logjam at first base now. The Sox could certainly use another bat with OBP potential, and Mauer could ideally fill a number of roles (first base, DH, even right field and catching instructor) as he transitions away from a superstar role into a complementary one.

(Of course, if Mauer is just replacement-level again in 2016, nearly any investment in him would be a bad one.)

I’m not sure that taking on a bad contract fits inside the old Red Sox wheelhouse, where they typically added players on shorter contracts and gave up guaranteed money in the legendary Adrian Gonzalez / Carl Crawford deal. But Dombrowski hasn’t shied away from taking on money in his previous regimes. This is definitely an option in play.

Option 4: Swap Future Value for Present Value

This is the type of thing that can get you fired in Toronto, but it is the hallmark of past Dombrowski teams. The Sox are positively loaded in the minor leagues, even after the Craig Kimbrel trade, and they have the unique ability to add major league talent — talent that could be expensive in terms of dollars, or much cheaper — to their roster. These are not deals that any team could make — but the Sox are in a position all teams wish they could at least consider: using talent instead of money to add stars.

If any player at all is on the market, the Red Sox are in play. If the Mets are sick of Matt Harvey’s attitude, the Red Sox are one of the few teams that could pay the freight to move him to Boston. He could be the new Massachusetts Bureau Chief. The same is true with Yasiel Puig in Los Angeles. These are players who won’t come cheap, but the Sox have the prospect depth to be able to make these deals … if that’s what they decide they want. This way, they could acquire impactful talent at a fraction of the cost a top-tier free agent would bring in.

Is this kind of move a good idea? Of course, that’s almost impossible to say up front. It has certainly worked for some teams — don’t you think that the Red Sox would have loved to have traded for Josh Donaldson instead of signing Pablo Sandoval? At the same time, not all of these types of trades work out — think the Padres and their acquisition of Wil Myers, which has been a mixed bag to date.

Option 5: Some Combination of No. 2 – No. 4 Above

In the end, I think this is the team’s most likely option. While I would absolutely love to see the Sox go out and get Zack Greinke or Jason Heyward, logic dictates that the team will use Dombrowski’s trading acumen and avoid linking themselves to one huge contract when they already have so many on the books. Especially with the free agent market a bit top-loaded, I could easily see the Sox being aggressive in the trade market to bring in one or two talented mid-tier players (think 2-4 WARP types), before reloading in the middle-to-bottom tier of free agency.

In today’s baseball economy, $30 million is hardly a fortune. The Twins probably have at least that much to spend this season. The Twins! The Red Sox could commit all of that to a single player, or they could leverage a creative trading GM, spend some of their prospect currency, and make that money fill more holes than just one.

The real takeaway here is that, unlike many teams, who are locked into a roster core and/or may not have the resources that the Sox do, all of these options are on the table. Other teams looking to rebuild may find themselves with some money to spend, but without the prospect resources, or the flexibility, to improve in other ways. No matter what ends up happening, you can’t say that the Red Sox don’t have choices during this critical offseason.

Photo by Peter Aiken/USA Today Sports Images

Going Deep

It took five long years, but Sandy Alderson’s plan finally came to fruition when the Mets clinched their first National League pennant since 2000 last week. Alderson took over as general manager in October 2010, and started from scratch by remaking the entire front office and roster. The result was an arduous rebuilding process that has culminated in a World Series berth this season. Alderson’s rebuilding strategy was successful, but, as The Boston Globe’s Alex Speier writes, it’s not a blueprint by which Dave Dombrowski and the Red Sox need to follow. Dombrowski, for his part, has already shown a desire to continue some of what Ben Cherington started. He promoted assistant GM Mike Hazen to Cherington’s old post, and has embraced the highly touted farm system he’s inherited. The Sox don’t need to tear down what they have. They just need to address their weaknesses, specifically pitching, while their system continues to produce potential everyday players. What the Red Sox can learn from the Mets, Tim Britton of the Providence Journal writes, is an effective approach to building a starting rotation. New York is in the World Series primarily because it has one of the best pitching staffs in baseball. The Mets owned the fourth-best team ERA (3.45) and ninth-best team DRA (4.14) during the regular season, while its four-man postseason rotation of Matt Harvey, Noah Syndergaard, Jacob deGrom and Steven Matz has excelled in October. This rotation isn’t a result of high price tags and free-agent signings, but rather good old fashioned homegrown development. Harvey, deGrom and Matz were all drafted by the Mets, while Syndergaard was acquired from Toronto for R.A. Dickey as a minor leaguer. Perhaps the solution to Boston’s search for an ace will also be found in its own organization as well in the form of Eduardo Rodriguez, or someone further down in the system such as Michael Kopech.

Brock Holt has developed into a fan and organization favorite over the last two years. He’s the consummate blue-collar player, he started off as an unknown thrown in the Joel Hanrahan trade with the Pirates and soon emerged as a hard-working, everyday utility player who’s also a pretty good hitter. Holt was recognized nationally for these efforts in 2015 when he represented the Red Sox in the All-Star Game. But where does Holt fit in with the 2016 team? MassLive.com’s Christopher Smith writes that Holt’s greatest value may not come as the team’s superutility man, but as a trade chip to acquire a reliever. Holt played seven positions in 2015 and slashed a solid  .280/.349/.379 over 509 plate appearances. His trade value may never be higher, and it may be enough to bring in the late-inning arm the Red Sox need. Meanwhile, the Sox have starting positions solidified throughout the field and positional depth and versatility in Deven Marrero and Travis Shaw. Their progress over the final month of the season only strengthens the case to consider moving Holt before his value dwindles.  

Quick Hits

The Red Sox will no doubt be looking for pitching this offseason. Given their struggles last year, they’d be best served finding a top-of-the-rotation arm, whether it be via trade or free agency. One potential target could be the Dodgers’ Zack Greinke. Scott Lauber of the Boston Herald examines whether or not Greinke, who is expected to opt out of his contract with LA, would be a fit in the Sox’s clubhouse. He certainly has the talent they’re looking for, posting a 1.66 FIP and 8.08 K/9 in a Cy Young-caliber season in 2015, but Lauber explains how Greinke’s past battles with social anxiety disorder and clinical depression may make Boston and its large media market far less appealing to the righty. That point, however, is moot given Greinke spent the last three years in LA’s maket.

Yoan Moncada has received nothing but high praise following an impressive first season in the Red Sox organization in which he posted a .315 TAv and .378 wOBA for Low-A Greenville. He donned the cover of Baseball America, was named the South Atlantic League’s top prospect and was considered by one scout to be the “closest thing” to Mike Trout he’s seen. But it appears this is the last anyone will see of Moncada until spring training. WEEI.com’s Rob Bradford reports that the 20-year-old second baseman will no longer be participating in the Puerto Rican Winter League due to a hand injury suffered after being hit by a pitch in an Instructional League game earlier this month. The Red Sox have yet to release an official diagnosis, but Moncada is reportedly still feeling discomfort from the ailment.

The Red Sox received good news last week when it was announced that manager John Farrell’s cancer is in remission. CSNNE.com’s Sean McAdam provides quotes from Farrell, who express relief and an eagerness to start preparing for next season.

In more surprising news, former Phillies GM Ruben Amaro Jr. was named the Sox’s new first base coach. Although it’s an unusual transition for Amaro, a former major league outfielder, he told ESPNBoston.com’s Gordon Edes that he had an “itch” to return to the field. Amaro will also be useful throwing batting practice, as he told reporters that he’s ambidextrous.

Longtime outfielder Torii Hunter announced his retirement on Monday. That’s good news for the Red Sox. Hunter slashed .321/.370/.482 in 113 career games against the Sox, although he’s most remembered in Boston for his tumble into the bullpen while chasing down David Ortiz’s game-tying grand slam in Game 2 of the World Series.

Photo by Steve Mitchell/USA Today Sports Images