Three toughest decisions for qualifying offers

With the World Series in the books -- congrats, Kansas City! -- the attention of the baseball world turns to the offseason, and the first deadline is quickly upon us: the qualifying offer. Teams have until 5 p.m. ET on Friday to decide whether to extend a one-year, $15.8 million contract offer to their impending free agents. Players then have one week to accept or decline the offer. If they reject it and sign elsewhere, their previous team receives a compensatory Draft pick in 2016, and their new team surrenders its top unprotected Draft pick.

In the first three years of the current system, 34 players have received an offer, and all 34 have declined it. What that indicates is that teams have been too conservative in making offers, in some cases leaving Draft picks on the board. Until we're no longer living in the world of a 100 percent decline rate, teams ought to be more aggressive in handing out offers. That reality means that we have some more borderline candidates than in years past -- and it's time to look at three of the toughest decisions that should end with offers.

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Remember: We're not concerned about the obvious slam dunks here, like Jason Heyward, Justin Upton and Zack Greinke (now that he has opted out). Remember, also, that players traded during the season are ineligible to receive an offer, so that counts out Yoenis Cespedes, David Price and Ben Zobrist, among others.

Brett Anderson, Dodgers
One of the primary reasons for a team to extend a qualifying offer to a mid-tier free agent is that even if you end up overpaying for a year, you're only committing to a single year, not many, and for a player like Anderson, that's a big deal. Besieged by injuries between 2011-14, he pitched a total of 206 1/3 innings over four seasons for the A's and Rockies. In 2015, Anderson stayed healthy enough to contribute 180 1/3 innings of league average pitching. (His 3.94 FIP was nearly identical to MLB's 3.96; his 3.69 ERA was better.)

Video: LAD@SF: Anderson pitches 7 2/3, allows two runs

The Dodgers, right now, have two truths. One is that their budget is essentially endless, which is to say that if Anderson can get $10 million coming off years of repeated injuries, $15.8 million coming off a solid, healthy season doesn't seem unreasonable. Two is that now that Greinke has opted out, Clayton Kershaw is their only healthy, reliable starter, depending on how you feel about Alex Wood. That's not going to cut it.

So while Anderson's top-level numbers don't seem eye-popping, there's value to baseball's foremost ground-baller (66.3 percent grounders, best among starters), particularly since he managed to control how hard those balls were hit very well. Anderson allowed a Statcast™ exit velocity on grounders of 88 mph or less on 22.6 percent of his batted balls, fifth behind some big names in Dallas Keuchel, Garrett Richards, Jake Arrieta and Tyson Ross. The Dodgers need him back, and they can afford the single-year overpay for his age-28 season. If Anderson decides he'd rather seek multiple years elsewhere, they'll happily collect the Draft pick.

Denard Span, Nationals
When healthy, Span is a solidly underrated outfielder, combining average-to-slightly-above-average offense with a quality glove and value on the bases (seven seasons with double-digit steals), attributes that earned him seasons of three or more Wins Above Replacement each year from 2012-14. Unfortunately for Span, the "when healthy" part of that failed him in 2015. He played in only 61 games, starting the year late due to abdominal surgery, missing time over the summer with back spasms, and finally seeing his season end in August due to hip surgery. Because Span will be 32 in February, the Nationals could reasonably conclude he's not worth the risk.

Video: ATL@WSH: Span makes a great sliding catch in center

On the other hand, there's plenty of reason to want him back, especially if it's for only one year. Though Bryce Harper is likely the National League MVP Award winner, Jayson Werth is about to turn 37 and is coming off the worst year of his career, meaning the Nats could have outfield depth questions without Span. Presumptive center-field replacement Michael Taylor, despite being a plus defender who hit what was at the time the longest homer of the Statcast™ era, hit an unacceptable .229/.282/.358 in 511 plate appearances this year.

There's also the question of what the risk really is in extending the offer. Span is arguably the best center-field option on the market, along with Dexter Fowler (Colby Rasmus and Austin Jackson seem safely a level below), and given that Span switched to Scott Boras as an agent just six weeks ago, it seems more likely than not that he'd decline the offer anyway. If not, why bother switching to Boras?

Marco Estrada, Blue Jays
Estrada made $3.9 million in 2015, so on the surface, it seems crazy to quadruple his salary.

Video: ALCS Gm5: Estrada dominates Royals, exits to ovation

Then again, what a player made before free agency shouldn't have any bearing on what he can make on the market, and this seems a perfect situation where both the player and team need each other. On Toronto's side, the rotation behind Marcus Stroman and R.A. Dickey is a big question mark. Price isn't likely to return, Mark Buehrle may retire, and despite a misleadingly good win-loss record, Drew Hutchison is hardly a lock to make the roster. The Blue Jays badly need a solid mid-rotation starter like Estrada, who we profiled here in September as a pitcher finding success thanks to high vertical movement and low ground-ball exit velocity.

While Estrada, 32, could probably find a multiyear deal if he were to leave as a free agent, his limited track record combined with a stacked pitching market (Price, Greinke, Jordan Zimmermann, Johnny Cueto, Wei-Yin Chen, Mike Leake, Scott Kazmir, Jeff Samardzija, Hisashi Iwakuma, Yovani Gallardo, Bartolo Colon and others are all likely to be out there) means he could find himself as the next Ervin Santana or Kyle Lohse. That is, a good-but-not-elite pitcher in his 30s with Draft-pick compensation on his head who can easily linger unsigned until spring.

The Blue Jays should make the offer to Estrada to protect themselves, but the best scenario here is for both sides to agree on a two- or three-year deal at around $10 million annually.