MLB free agency: 10 key questions with Nationals' stars, Gerrit Cole, Scott Boras set for big offseasons

Come Monday, Major League Baseball's exclusive post-World Series negotiating period will end, bringing with it the start of the free-agent market. While there won't be a slew of signings out of the gates -- at least not at the frantic pace employed in other sports -- this winter could be a fun one given the amount of star power present at the top of the market.

To help everyone prepare for and/or catch up on free agency's biggest storylines, we've decided to outline our 10 biggest questions entering the storm. 

usatsi-130644251.jpg
Both Anthony Rendon and Stephen Strasburg are free agents. USATSI

1. Will the Nationals retain their stars?

The good news for the Nationals is they just won the World Series in seven games against the Houston Astros to cap a wild October run. The bad news for the Nationals is both right-hander Stephen Strasburg and third baseman Anthony Rendon are headed for free agency.

The Nationals permitted Bryce Harper to walk last offseason, but only after making an offer that was loaded with deferrals. Presumably the Nationals will attempt to retain both Strasburg and Rendon, though it's unclear if they'll rely upon deferred payments as they have in the past.

One thing is for sure: The Nationals have plenty of incentive to retain the pair. Besides having just won the championship, the Nationals have significant payroll space available to them. Currently, they're projected around $105 million, including arbitration raises. They entered the 2019 season with a payroll of $197 million, suggesting they could have $90-plus million to spend.

That doesn't mean the Nationals will re-sign both Strasburg and Rendon -- they're likely to face steep competition on both, including from their rival Philadelphia Phillies . But it does seem likely that the world champions keep at least one of the two.

2. Can Cole make history?

Strasburg isn't the only big-name starter available. Heck, he's not the only big-name starter from the World Series available. Gerrit Cole, formerly of the Houston Astros, is also out there.

Cole and agent Scott Boras will presumably be looking to make history by signing the richest free-agent contract for a pitcher. Currently, that title is held by David Price, who signed a seven-year deal worth $216 million prior to the start of the 2016 season.

Four pitchers in league history have signed deals worth more than $200 million -- Price, Max Scherzer, Clayton Kershaw, and Zack Greinke. Cole stands to be the fifth or sixth, depending on what Strasburg gets and when he gets it -- and he might end up No. 1 in another regard. 

3. How many texts will Boras send?

Boras, by the way, is in for a hectic winter. Not only does he represent all three of the free agents named so far -- Strasburg, Rendon, and Cole -- but he's also the agent for J.D. Martinez, Hyun-Jin Ryu, Dallas Keuchel, Mike Moustakas, and Nicholas Castellanos, among others.

Boras better have multiple devices and multiple chargers for those devices. He'll need 'em.

Los Angeles Angels Introduce Joe Maddon - News Conference
Joe Maddon wants you, top free agent pitcher to be named later. Getty Images

4. Will the Angels shop at the top of the market?

The Angels have already made one headline-grabbing addition this offseason, hiring Joe Maddon as their new skipper. Owner Arte Moreno has already conceded payroll will increase, too.

To what extent remains unclear. The Angels currently have $115 million in guaranteed commitments for next season, with another $27 million in projected arbitration prizes. (The arbitration figure is likely to drop with non-tenders.) Were the Angels to stand pat -- and they won't -- they would have a payroll around $142 million. As a franchise, they've never had an Opening Day payroll of $170 million or more.

As such, there are a few questions facing the Angels: 1) how much Moreno will permit them to spend? and 2) who will they spend it on? Presuming the answer to the first part is "a lot" then it stands to reason they should invest in starting pitching help, which could put them in play for Cole, Strasburg, and the other top arms available. 

5. Is Bumgarner bound for the Bronx?

One of those other top arms available is Madison Bumgarner, who was connected to the New York Yankees (among other teams) at the deadline. Expect that interest to be rekindled.

The Yankees are expected to check in on Cole, and will presumably do the same with Strasburg. If they don't find either's asking price to their liking, they could pivot to a downmarket option like Bumgarner, who has a track record of being an above-average starter but lacks the top-end stuff deployed by both Cole and Strasburg.

With Ryu presumably returning to the Los Angeles Dodgers and the Yankees having already passed on signing Dallas Keuchel last winter and this spring, Bumgarner might represent one of Brian Cashman's few opportunities to land an affordable, high-quality starter.

6. Will third time be charm for Moustakas?

You have to feel a little bad for Mike Moustakas, who is now on his third try as a free agent. 

Moustakas homered 38 times during the 2017 season and had to settle for a one-year deal (with an option) worth $6.5 million; he then homered 28 times and had to settle for a similar deal worth $10 million. Now, Moustakas is coming off a 35-homer season. Will this be the year he lands a guaranteed multi-year pact?

To be clear, Moustakas is more than just his home-run total. He's posted OPS+ of 117, 107, and 114 in those seasons. He's also shown a willingness to play other positions, be it second or first base. In theory, his consistency and versatility should work in his favor. In practice … we'll see.

7. Who will become Puig's friend?

Finding a landing spot for Yasiel Puig is harder than it would seem. In addition to being one of three right-handed-hitting corner outfielders, alongside Nicholas Castellanos and Marcell Ozuna, he remains a polarizing (if productive) figure, limiting his prospective market.

In our free agent rankings post, we named the St. Louis Cardinals, Texas Rangers, San Francisco Giants, and Seattle Mariners as plausible landing spots for Puig. Even if you expand it to opportunistic teams -- think the Tampa Bay Rays, Cleveland, and perhaps even the Angels -- there aren't that many teams in the market for another non-elite right-right corner bat.

It'll be interesting to see where Puig ends up, then, and for how long.

8. Can Minnesota replace its rotation?

The Twins were one of the feel-good stories of the spring and summer, winning the American League Central after a busy winter. 

What will the Twins do for an encore? How about replace almost their entire rotation? Jose Berrios is the only member of Minnesota's rotation expected to return. Otherwise, Jake Odorizzi, Kyle Gibson, Michael Pineda, and Martin Perez (who has a club option) will all hit the market.

The Twins do have some internal options to consider -- Brusdar Graterol and Randy Dobnak among them -- but they're likely to add a couple of starters through free agency. In other words, keep an eye on Minnesota as it pertains to the second and third tiers of starters.

9. Are there any sleeper teams?

Of course. The Chicago White Sox figure to do something as they try to shift from rebuilder to contender; the Texas Rangers have a new ballpark to open and a rotation to upgrade; and the Cincinnati Reds are presumably looking at wholesale changes if they don't reach the postseason (or come close to it), which may influence their decision-making process this winter. The Toronto Blue Jays should also drop some coin, but it's anyone's guess as to how much.

10. Will the top free agents be signed by spring?

Gosh, here's hoping. Unfortunately, it seems more likely than not that one or two top free agents are still out there come February. In part because of how stingy the league has become in handing out big contracts to non-elite players, and in part because so many of the top free agents are represented by Boras, who is more than willing to take his time in negotiations. 

CBS Sports Staff

R.J. Anderson joined CBS Sports in 2016. He previously wrote for Baseball Prospectus, where he contributed to five of the New York Times bestselling annuals. His work has also appeared in Newsweek and... Full Bio

Our Latest Stories