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Gerrit Cole watch, big spenders and more: Passan answers 20 winter meetings questions

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Boras expects Cole's free agency to be quick (1:01)

Agent Scott Boras says Gerrit Cole's free agency will be "very different" than Bryce Harper's due to the demand for starting pitchers. (1:01)

SAN DIEGO -- The winter meetings, once the domain of blockbuster trades and megabucks free-agent signings, have in recent years gone into the sort of hibernation typically associated with the season. They've been defined more by their inaction than their action. Last year's big move: Philadelphia guaranteeing $50 million to Andrew McCutchen. The year before: The Yankees announcing the acquisition of Giancarlo Stanton -- a deal done before the meetings even began.

The last big trade took place in 2016, when Boston acquired Chris Sale. The last foundational free-agent signing? Jon Lester's six-year, $155 million deal in 2014 with the Chicago Cubs. The winter meetings were once a place where Bill Veeck sat at a table, posted a sign that said "Open For Business" and proceeded to make six trades. Today general managers tend to prefer texting.

All of this is to say: It's time for a representative winter meetings, one that can compete with the NFL and NBA and bowl season and college basketball. Whether the 2019 version, which kicks off Monday morning at the Manchester Grand Hyatt here, offers as much depends on how motivated and inclined executives and agents are to strike deals. Since we know where all of those things could take place, let's play a game of 20 Questions to answer the who, what, when and, most important, why.

What's this week going to be like?

Some free agents will sign here. Maybe even one who is going to get more than a quarter-billion dollars. Some trades will happen here. Maybe even one with a franchise-type player. These meetings, according to a number of the sport's power brokers, have a sense of momentum thanks to a free-agent market that has roared -- or at least rumbled -- in comparison to those in recent years.

Then again, it's worth remembering that the winter meetings last only through the Rule 5 draft Thursday morning, and no grand incentive exists for teams to do business here. Whereas once the meetings provided a face-to-face opportunity for deals to be struck, the constant communication among teams looking to lock down trades -- and between teams and agents interested in making deals for free agents -- have made the winter meetings something of an anachronism.

Which is part of why the baseball establishment is hoping something changes. Especially considering there has been momentum toward one of those monster deals actually happening.

So Gerrit Cole is signing?!?!

Slow down, chief. No matter how many times someone begs, "Announce Cole" on Twitter, the quality of initial offers -- which, according to sources, are expected to be considered by Cole during the meetings -- will dictate how quickly the best player on the market and best free-agent pitcher ever signs.

Maybe it will be here. Maybe it won't. Again: There is nothing forcing Cole to choose his destination now, and there is nothing to be gained by teams trying to give Cole a take-it-or-leave-it offer, because if even the slightest chance it could backfire exists, the risk of such a play would be uncharacteristic for typically risk-averse teams such as the New York Yankees and Los Angeles Dodgers -- or even the Los Angeles Angels, who have been burned by bad free-agent deals.

Hold on. Did you just call Gerrit Cole the best free-agent pitcher ever?

Yup. And this isn't a prisoner-of-the-moment thing, either. Consider:

• Cole is 29 years old, and in an era when age matters greatly, he hits free agency younger than David Price, Max Scherzer, Zack Greinke, Jon Lester, Patrick Corbin, Johnny Cueto, Cliff Lee, Zack Wheeler, Jordan Zimmermann and Kevin Brown -- all of whom received $100 million-plus deals. The only younger nine-figure pitchers: CC Sabathia and Barry Zito, both of whom were 28. The best argument is for Greg Maddux, who was coming off a Cy Young-winning season in 1992 at 26 -- and is an all-time-great Hall of Famer.

• But neither Maddux nor Zito nor even Sabathia had anything close to Cole's raw stuff. His fastball, slider, curveball and changeup are the best array of pitches in the major leagues. Cole's fastball averaged 97.2 mph last season, behind only Noah Syndergaard's 97.7 mph among starters. In his seventh season, Cole threw harder than ever. That sort of pure ability is nearly unmatched.

• When he is controlling and commanding the ball, which Cole usually is, you can get rid of "nearly" -- it is entirely unmatched. It's not like Cole simply has a blessed right arm. He knows how to maneuver around the strike zone, too.

• How's this for what it manifests: 20-5 record, 2.50 ERA, 212 1/3 innings, 326 strikeouts, dazzling postseason -- a completely nonpareil walk year.

• Oh, and he's durable, too. Over the past three years, Cole has made 98 starts and thrown 200-plus innings every year. He has never suffered an arm injury or required surgery. And it's not like he's going into free agency with an odometer that needs the Ferris Bueller treatment. Sabathia's career innings (regular season and playoffs) going into his walk year: 1,694.1. Zito's: 1,474.2. Cole is at 1,260.2.

• One thing teams took away from Cole's meetings with them, according to sources: For all the objective analysis laid out above on how great he is, his soft factors impressed, too. The intelligence, the desire to win, the reports on how hard he works, the leadership, the yearning to be the absolute best at what he does. Cole is the full package.

If being the absolute best matters, would he really risk pitching in Yankee Stadium?

This sounds like a troll question. It's not. In fact, this has nothing to do with whether Cole has the mettle to pitch in New York. He does. It's more a devil's advocate-style question -- the sort Cole is even likely to ask -- about what pitching in New York could potentially do to his legacy.

Pitching in the new Yankee Stadium can be positively exhilarating, especially if the Yankees are as good as they expect to be and play as much in October as they plan to. It is also exactly the sort of ballpark that vexes pitchers like Gerrit Cole.

Cole is a fairly extreme fly-ball pitcher. Last season, according to ESPN Stats & Info, he had the seventh-highest fly-ball rate in MLB. His opposite-field fly-ball rate was 10th in the American League. Yankee Stadium, meanwhile, had the fifth-highest home run rate allowed in the league last year. And the opposite-field home run rate at the stadium? The highest in MLB.

Now, Cole managed to pitch well last year while giving up an excessive amount of home runs per fly balls hit, so maybe this isn't an issue. But Cole is competitive. He wants to be great, and greatness often is measured by numbers, and the notion that the only numbers important to Cole are the ones on the contract offer is incorrect.

Cole isn't going to pick the Dodgers just because Dodger Stadium is arguably the best place to pitch in the major leagues. He isn't going to pick the Angels only because he'll give up fewer home runs. But he will think about it because he is bright and meticulous and introspective and sees this choice as much more than commas and zeroes.

What's he gonna get?

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Where will Gerrit Cole and Anthony Rendon land?

Gerrit Cole and Anthony Rendon are the top free agents this offseason. Jeff Passan and Keith Law predict where they will land.

Multiple sources believe the bidding will begin in the seven-year, $250 million range and move up from there. If the offers are similar, teams may have a choice to separate themselves: Bump up the per-year value or add the extra year? It's a fair question: Would it be better for Cole to get $37 million a year for seven seasons or $35 million a year for eight?

In the end, that latter figure sounds about right. A $35 million-per-annum payday would beat Greinke's average annual value record. Eight years would supersede Price and a host of others (seven). So the guess -- and it's nothing more than a guess at this point: eight years, $282 million, for $35.25 million per year.

Would you please move on from Gerrit Cole?

Fine. But don't you want to know who's going to sign him?

Who's going to sign him?!?!

I don't know.

You're the worst.

That's not a question.

You're the ... worst?

Yes.

Now that we've got that established, who aren't we going to be hearing much from this week, just so we can get them out of the way?

There are about a dozen teams that have shown no interest in playing for even medium-dollar free agents. Some of them, like the Baltimore Orioles, Detroit Tigers and Miami Marlins, don't have much of near-term value in trades, either, and aren't expected to be terribly active in either market.

Kansas City continues to listen on super-utilityman Whit Merrifield, but the ask is rightly big. Pittsburgh could move center fielder Starling Marte, particularly with a paucity of available players at the position. Teams have continued to poke around on outfielder Mitch Haniger with Seattle in hopes that GM Jerry Dipoto might get twitchy.

Colorado is hamstrung by bad contracts and wants to dump them, which ... good luck. Oakland is excellent but doesn't have payroll flexibility, which is a shame because excellence warrants supplementation. Cleveland isn't quite as excellent but also doesn't have money to spend, which stinks, too.

The three final teams -- Boston, Houston and the Chicago Cubs -- are big spenders whose owners aren't inclined to spend more.

Whose owners aren't inclined to ... what?

Welcome to baseball in 2020: When you have the core of a team capable of winning a championship, and you don't do everything you can to ... win a championship.

OK. Then who is spending?

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Top offseason spenders might include Angels, Padres, White Sox

Keith Law and Jeff Passan predict the teams that will be the biggest buyers this offseason.

Ten teams ostensibly fall into this grouping, though there are some caveats. The Toronto Blue Jays keep saying they're going to expand their payroll, but the industry tends to collectively nod and say, "uh-huh" because they still haven't. That team used to be the Chicago White Sox, until they gave $73 million to Yasmani Grandal and $50 million to Jose Abreu and offered $125 million to Zack Wheeler only to see him take $118 million from the Phillies instead. Cole and Stephen Strasburg may prove too rich for these profligate White Sox's blood, even though either would be perfect to lead their rotation going forward. That doesn't mean Chicago is done. Ditto Cincinnati, which missed on Grandal and Wheeler but gave Mike Moustakas $64 million and have tens of millions more to spend.

Who's left? A lot of big boys. (Apologies to Minnesota, which is a medium boy but here because it needs pitching and is trying for Madison Bumgarner and Hyun-Jin Ryu.) The Yankees, Dodgers, Nationals, Phillies, Angels and Rangers are the half-dozen teams capable of dropping nine figures on a guy without blinking.

The Phillies are a bit of a wild card. They are not full-bore pursuing any of the top free agents but have the financial wherewithal to jump in should the market take an unexpected dip. The Rangers are focusing on third baseman Anthony Rendon, who's likely to cost upward of $235 million. The Dodgers are in on him, too, as well as Cole and Strasburg, which gives them options. The Yankees are Cole, Cole, Cole, with Strasburg as the backup date if Cole goes to prom with the Angels, who also could pivot to Strasburg.

The Nationals are interesting. Owner Mark Lerner last week told NBC Sports Washington that they "really can only afford to have one of" Strasburg or Rendon.

He really said that?

He did! What made it so great was not just that the Nationals won the World Series this year and the financial windfall accompanying it will be worth tens of millions of dollars, if not more, for the team. No, it's that the Nationals clearly showed they could afford both before they won their championship.

The Nationals offered Rendon a seven-year contract extension worth more than $200 million in September, according to The Washington Post. At that time, Strasburg still had not opted out of the four years and $100 million remaining on his deal. Say the Nationals had lost in the wild card and Strasburg never had his brilliant October and World Series MVP. Or maybe he suffered some sort of an injury during the postseason and decided not to opt out. Rendon could have accepted that offer, and Strasburg could have stayed, and that would've been $300 million right there.

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Strasburg in line for megadeal after opting out of contract

Jeff Passan and Keith Law discuss the near-limitless market for Stephen Strasburg and the various teams that might be in line to pay him.

Now, the prices have changed. Rendon is going to get his Nolan Arenado-type contract. Strasburg is looking at $180 million-plus -- maybe even as much as $200 million. That's another $100 million on top of what they were willing to commit. And wouldn't you know? The Nationals just happen to have come into a windfall this year that gives them tens of millions of dollars. And they won the long-contested lawsuit over local TV rights fees that should infuse them with more cash.

So, yes. The Nationals can afford Rendon and Strasburg. If they don't sign them, just know: That's a choice, plain and simple.

So who else's name are we going to hear this week?

There's going to be a lot of Bumgarner, who might be in the best position of any remaining free agent. He'll cost less than half as much as Cole. He's more than a year younger than Strasburg. He appeals to a wide range of the spenders. His decision could come as early as this week.

What remains of the top-end relief market should move soon. Teams expect Blake Treinen, who was non-tendered by Oakland last week, to sign here. The other big-reward reliever, Dellin Betances, could find his team as well.

Josh Lindblom, who is coming back to MLB after a successful three-year run in Korea, will sign at the meetings. Japanese slugger Yoshitomo Tsutsugo has until Dec. 19, when his posting window runs out, to sign.

The Astros, Angels, Tigers and Pirates are among the teams still looking for catchers after that market thinned out with a rash of early signings. They could find partners in a trade, too, as could the teams looking for a third baseman, and all you need to do is go to 1060 West Addison.

Who are you, Elwood Blues?

One must wonder what ol' Elwood would think of the Cubs pursuing potential trades of core players. This isn't, as some have speculated, a money dump or an admission that they're not trying to compete or anything of the sort. Things got stale. Change for change's sake is irresponsible. Change for culture's sake is crucial.

So, yes. You may be hearing Kris Bryant's name. Because Bryant is going to make upward of $20 million in arbitration this year and because there's a chance -- albeit a slight chance -- he wins a service-time grievance and becomes a free agent after 2020 instead of 2021, the return in a trade for him might not be as franchise-changing as one would think.

The allure of Willson Contreras is strong. He's young. He's a catcher. He's cheap. He has weaknesses certainly -- framing metrics are not a fan -- but more strengths. You may be hearing his name, too.

While it's possible the Cubs get through the week doing nothing, the winter meetings do tend to stir something in them. There was Lester. And the $56 million signing of Ben Zobrist. And the $180 million signing of Jason Heyward that happened the day after the meetings ended. It is president Theo Epstein and GM Jed Hoyer's style to make this week interesting.

Who else is in good position?

Ryu and Dallas Keuchel, the two veteran left-handers. In years past, they might have been troubled for a robust market -- and by years past, in Keuchel's case, that means last year -- but so many teams need pitching and potential impact pitching, if they miss on Cole, Strasburg or Bumgarner, the could well turn to Ryu and Keuchel.

Both of whom, by the way, are represented by agent Scott Boras. As are Cole, Rendon, Strasburg and Nicholas Castellanos. Meaning Boras dictates a significant amount of what's bound to go on this winter -- and this week.

Who are some other big names?

William Van Landingham. Kirk Dressendorfer. Tim Spooneybarger. Jarrod Saltalamacchia.

You really are the worst.

Pretty much.

Let's finish this out with some quick hitters. Best non-Boras pitcher and position player remaining?

Pitcher: Bumgarner. Position player: Josh Donaldson, who is very similar to Bumgarner in that he's an excellent option for the teams that aren't in on Rendon -- and could force the hands of the teams that are in on Rendon by signing sooner. Donaldson also could wait, knowing that the teams that don't win Rendon will be even more desperate than before and might pay a higher price knowing the finite options.

Why is Didi Gregorius the only guy in Keith Law's Top 50 you haven't talked about?

Nothing personal. Gregorius' market is actually good. Teams say the longtime Yankees shortstop is positioning himself as a potential second baseman and third baseman, too. Gregorius is coming off a disappointing year in which he hit .238/.276/.441. At the same time, he doesn't turn 30 until spring training, he has the Phillies and Reds and others trying to sign him, and he'll have his choice of a multiyear deal or a one-year pillow contract to let him re-prove his worth.

Anything else to keep an eye on?

How much the thin outfield crop -- Castellanos and Marcell Ozuna -- manages to get paid. When the sub-Treinen/Betances market, starting with Will Harris and moving to Daniel Hudson, gets going. The dam breaking on the midtier pitchers, the ones just below Jordan Lyles -- whom Texas gave $16 million -- like Alex Wood, Tanner Roark, Homer Bailey, Brett Anderson, Wade Miley and Julio Teheran. Same for the secondary outfield department: Yasiel Puig, Kole Calhoun and even Brett Gardner, who long has been expected to re-sign with the Yankees.

Some parting advice for those of us tuning in to the winter meetings?

Don't stay up late waiting for rumors. It's not worth it.

Don't fall for fake Twitter accounts. It's not worth it.

Don't expect anyone from the Astros to say anything about their sign-stealing scandal. It's not worth it (for them).

Most of all, don't get angry at your team for doing nothing. Sometimes the best move is the one you don't make.

But then again, as the Cubs showed here five years ago with Lester, sometimes the best move is the one you do make. And the winter meetings, the place to do big things, is far from the worst place to try.