As we announced yesterday, we’re rebooting the MLBTR Mailbag series after a seven-year layoff. We’ve already received a large number of questions, and there’s no way to get to all of them, but I’ll tackle a handful in today’s post as well as each Monday from here on out. Remember that you can submit questions for next week’s Mailbag, via email: mlbtrmailbag@gmail.com.

On to the questions…

Does it make sense for the Phillies to sign some top tier free agents like Heyward and/or Greinke? A lot of money is off the books, and the Phillies have some promising prospects coming up within the next year or two. The first year of the deal may be rough for the newly-signed, but after that the Phillies look to be in a good position to compete. Is this a tough sell to the free agents? — David M.

From a financial standpoint, the Phillies would be in excellent shape to take on a long-term commitment. Philadelphia has just $23MM on the books for the 2017 season and no players guaranteed any money beyond that season, save for a $2MM buyout on Matt Harrison’s option. Practically speaking, it doesn’t make much sense for the Phillies to spend aggressively on an aging free agent like Greinke. As you noted, they’re unlikely to compete in at least the first year of a free agent deal and probably the second as well. By the time 2018 rolls around, Greinke would be into what are typically the decline years for a pitcher. A younger free agent like Heyward, on paper at least, could make some sense as they can afford him, and he’ll be in his prime when the Phillies hope to contend again. However, premium free agents typically prefer to sign with winning clubs — or at least clubs that have the possibility of doing so — and the Phillies have been vocal about their current rebuild.

Philadelphia does need to fill out its roster, but I’d imagine that the team’s free agent expenditures will be second- or third-tier free agents designed to soak up innings, as the Twins did with Ricky Nolasco and the Astros did with Scott Feldman in the 2013-14 offseason (obviously, with the hope for better results than Nolasco has delivered). That might mean someone like Ian Kennedy, though as the Cubs experienced with Edwin Jackson, it can be dangerous to give multiple years to a free agent who isn’t expected to play on a contender until the backside of the deal. Alternatively, the Phillies could be open to more buy-low options on shorter contracts, as they did this season with Chad Billingsley (again, with the hope for better results). Doug Fister is one such option, and Billingsley, Brandon Morrow and Brandon Beachy could also fit that mold. The Phillies could also exercise their financial muscle and lack of long-term commitments to “buy” a prospect — absorbing a Nolasco-like contract in its entirety in order to land a nice prospect from the team whose burden they are relieving while adding a serviceable arm in the process.

What kind of contract can we expect Jeff Samardzija to get in the off season? — Victoria R.

Entering the season, I thought Samardzija had a clear shot to blow past $100MM with a repeat of his 2014 campaign, but he’s gone the opposite direction. Samardzija’s strikeout and ground-ball rates have plummeted, and his ERA has spiked to 4.64 — the worst of his career since joining the rotation. FIP, xFIP and SIERA all come in over 4.00 as well.

There are some positives to Samardzija, though. He’s still averaging 94.2 mph on his fastball, his BB/9 rate is south of 2.00 for the second straight season, and some of his struggles can be attributed to the fact that Chicago’s defense ranks 28th in baseball in Defensive Runs Saved and Defensive Efficiency as well as 29th in Ultimate Zone Rating. With a better defense behind him — even a league-average defense — Samardzija’s bottom-line numbers would probably be better, though his BABIP-against stands at a reasonable .305, indicating that he may be more a victim of unfortunate sequencing.

Scouts love Samardzija’s arm and competitiveness, and by season’s end, he will very likely have turned in his third straight 200-inning season. As such, I can still see a nice multi-year deal, but barring a huge finish, I’m taking the under on $100MM and on five years as well.  A four-year deal worth $16-20MM annually is possible, and he can improve his earning power with a big showing over his final eight starts. He fired seven one-run innings on Aug. 19 but was shelled for five runs in 5 2/3 innings tonight, so he’s not off to a great start in terms of altering his fate with a strong finish.

Some might suggest that Samardzija will be forced to sign a one-year deal to rebuild his value, but he’s already going into his age-31 season next year, and delaying the prospect of a significant payday until a contract that would begin at age 32 may not hold much appeal. Players typically don’t want to take one-year deals unless they’re forced to by injury, and I don’t expect Samardzija to be any different.

Hey gang, with [Khris] Davis’s recent hot steak, coupled with the Brewers calling up [Domingo] Santana, do you see the Brewers dealing Davis to make room for Santana this winter? — Jason M.

I’d imagine that the new Brewers’ general manager, whoever it ends up being, will be open to listening to offers for Davis and much of the roster he inherits. There’s no real need to move Davis, with the possible exception, as you said, of freeing up playing time for Santana. There are a number of ways that both could be worked into the lineup though, as either Davis or Ryan Braun could conceivably put in some work at first base over the spring. Santana also has some experience in center field and has appeared there since coming up with the Brewers, so he could continue to get some seasoning there in 2015. While he’s not a long-term answer in center, Santana could be a stopgap solution for the Brewers as they wait for Brett Phillips’ development to continue. They could use 2016 — a rebuilding season — as a means of measuring whether or not Santana can hit consistently in the Majors and deal with the potential corner outfield logjam down the line if and when Phillips is ready.

What if the Yankees had simply let Sabathia go when he opted out a couple seasons ago? Surely his monster salary could have been better spent on a different pitcher or two. Maybe, and I say maybe, he earned his first few years of salary, but why not let him go when he was obviously in steep decline? — John M.

The Yankees’ decision to tack on one year and $30MM in guarantees (plus a vesting option) to Sabathia’s deal was obviously driven by the fact that the lefty had the right to opt out of the contract he signed in the 2008-09 offseason. As MLBTR’s Tim Dierkes explored in detail last year in a deep look at on opt-out clauses, Sabathia was able to land that provision in his free agent deal because he held so much leverage as an outstanding, youthful starter. Effectively, he bought himself another bit of leverage further down the line, which he and his representatives were able to employ. (Sabathia actually reached a new deal before opting out, it should be noted.)

There’s certainly something to be said for avoiding contracts of that magnitude — especially for pitchers, who are more prone to breaking down than position players. But to suggest that Sabathia was in a steep decline at the time he could have opted out isn’t really accurate. From 2009-11, Sabathia averaged six WAR per season, and his 2011 strikeout and walk rates were his best since 2008. Sabathia declined more steeply and more rapidly than most pitchers do, and that’s harmed the Yankees, but that future wasn’t known by the Yankees following the 2011 season.

It’s easy to apply hindsight and say the Yankees should’ve let Sabathia walk. But there were a lot of reasons to like the deal at the time, too, considering the market context. Sabathia was entering his age-31 season — a pretty typical age for the game’s top free agent pitchers to receive contracts of six or seven years of length. Restructuring his contract was akin to signing a pitcher who would’ve been far and away the market’s most desirable starting pitcher. C.J. Wilson got the largest contract of any starter that offseason, followed by Mark Buehrle, and only Yu Darvish would’ve rivaled Sabathia in terms of ace upside, but how he’d transition to the majors was not yet known. Sabathia was coming off a six-WAR season with the Yankees after pitching 237 innings for a second consecutive season. His open-market position would’ve been similar to that of guys like Max Scherzer and Jon Lester this past winter — both of whom landed huge contracts over seven and six years, respectively.

As Tim noted to me in discussing this matter yesterday, it seemed at the time that New York would have to guarantee two additional seasons to get a deal done and keep Sabathia from electing free agency. While the vesting option ($25MM with a $5MM buyout) could still add to the tab, the deal that was reached represented a solid value for the Yankees given the context when the decision was made.

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