Keith Law and Jeff Passan explain why the pressure is on the Yankees and Cubs to improve their rosters this offseason. (2:14)

On the day after the World Series, an agent for a prominent free agent this winter expressed shock at how busy his day had been. In the past two seasons, free agency began with a whimper -- few texts, fewer calls. Thursday was different.

"I don't know if it's going to mean anything," he said. "But at least they're acting interested."

Free agency is at the heart of the discord between Major League Baseball and the MLB Players Association. The misgivings started in the winter of 2016-17, graduated to anger a year later and remained that way last winter. And with free agency starting Monday at 5 p.m. ET, what form it will take is a central topic as the hot stove season kicks off.

Offseason maneuvering once took place over a frenzied, six-week period. In recent years, it has stretched into four months of posturing and parrying. And with that new paradigm, it seems the perfect opportunity to play a game of 20 Questions about the winter of 2019-20.

All right. Just rip off the Band-Aid. Is this offseason going to be a protracted mess?

Probably! There are countless factors at play here -- this big, messy stew of changing valuations, disincentives to spend, no penalties for not spending, greater understanding of the aging curve and dozens more issues. And it's the same as it was last year and the year before. Why, then, would the behavior of teams change?

It's just a reality that both sides acknowledge is unlikely to end until this collective bargaining agreement expires in 2021. Midterm talks between the league and union to address economic issues went nowhere, and that almost certainly won't change. And while other teams talk about being aggressive this winter, you've got the Boston Red Sox -- much more on them later -- wanting to slash payroll.

What's saddest is that just about everyone in baseball recognizes that a winter in which the best players don't sign until the new year isn't ideal for the game. If these early calls to agents wind up being significant -- four others confirmed to ESPN that conversations have been much more active in the days leading up to free agency -- then the return of competitiveness in free agency will be the story of the winter.

Here's the issue: The players think it's eyewash -- a beloved baseball term that means something done purely for optics. Teams are changing things up, hoping players will bite on below-market deals early. The upshot of recent free agency is a deep, deep distrust of teams' intentions. Even if teams are evolving, placing an emphasis on winning, the players aren't buying it. Talk is empty. They want substantive action.

OK, Debbie Downer. Why can't it be like the NBA or the NFL, where everyone signs quickly?

It could be. In fact, last month MLB proposed a winter meetings deadline for the signing of multiyear contracts. The union rejected it because for whatever benefits it might have offered for getting deals done early and keeping baseball in the news during the offseason, the possible negative outcomes -- teams trying to squeeze players worthy of multiyear deals into accepting one-year pacts -- made it a complete nonstarter.

There are plenty of other ways to incentivize teams to spend early, but the foundational difference between MLB and the other two leagues is that baseball operates in an uncapped system. Football and basketball teams have limited amounts, and each player falls into a category with a near-set price. MLB teams can spend as much or as little as they want. So if a baseball player believes X is fair value and a team is offering X minus $10 million, the free market -- not a player's place inside a system with a finite amount of dollars -- will render that judgment.

Sometimes waiting helps. Sometimes waiting is boneheaded. Teams almost always wind up in a better position by waiting. Players have a far spottier track record when waiting. Teams recognize this and thus could be compelled to push for earlier deals, hoping to jump the market and prey on players who no longer believe free agency to be the paradise of their dreams.

So who's the best free agent?

play 2:31 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.

Well, if you ask Keith Law, it's Anthony Rendon, the all-world Washington Nationals third baseman who spent October crushing baseballs and winning a championship. Rendon, 29, is the goods: a superb hitter with elite bat-to-ball skills, power, a great eye and a well-above-average glove.

I think it's Gerrit Cole, the best pitcher in the world at the moment. Cole also might be in the best position for a free-agent pitcher in baseball history. He is 29, coming off a year in which he struck out 326 batters in 212⅓ innings, doesn't have excessive wear and tear on his arm, holsters a truly elite four-pitch mix, has avoided any serious arm issues and brings both the personality and leadership traits teams crave. He's big, he's strong, he's smart, he's motivated. It's hard to find a flaw.

Which of you is right?

Only one of them is so serious about free agency that less than half an hour after his team lost the World Series, he said he no longer worked for that team and wore a hat bearing the logo of his agent's company during his postgame debrief.

Huh?

Oh, yeah. Winter is coming, and Scott Boras is the Night King.

The famous (and infamous) agent is back with a class of clients that gives him a disproportionate amount of control over the market. Cole wore the Boras Corporation hat. Boras represents Rendon, too, as well as Rendon's Nationals teammate Stephen Strasburg, who opted out of the final four years and $100 million of his current contract to strike free-agent riches. Those are the top three players in the class.

There are plenty more. Hyun-Jin Ryu, who for most of the season looked like the NL Cy Young favorite? Boras guy. Nicholas Castellanos, arguably the Cubs' best player over the final two months? Yup. Mike Moustakas? Dallas Keuchel? Boras, Boras.

Nobody is more comfortable waiting for the right deal. Sometimes it comes along, as it did with Bryce Harper last spring. In other cases, as with Moustakas and Keuchel, the market never met expectations. Exactly how Boras approaches this winter could be a key to understanding how it unfolds.

How much are the big three going to get?

Well, Cole is going to become the highest-paid pitcher in history. That title currently belongs to David Price, who signed a seven-year, $217 million deal with Boston before the 2016 season. He was a year older than Cole, had 250 more innings on his arm and didn't possess nearly the same arsenal. Price was a really good free agent. Cole is just better.

The question is not whether Cole will get years or dollars. It's whether he can get both. He could reasonably pursue an eight-year deal. He could reasonably pursue a $35 million-a-year salary. (Zack Greinke got $34.4 million per annum the same offseason as Price, though a chunk of it was deferred.) Just how hot and heavy the bidding gets -- and if it's not blazing and substantial, why not? -- will determine whether the eight and $35 million meet up for a $280 million total.

2019-20 Hot Stove League Check in on the trades, free-agent signings and more, from now until pitchers and catchers report. MLB Offseason page »

Rendon could take a different route. Multiple executives interested in signing Rendon believe he might be willing to take a short-term, high-average-annual-value deal. The notion of paying him $40 million a year for five years is realistic. Now, if Rendon wants to eschew that and go for the jackpot? Nolan Arenado, to whom Rendon compares well, got eight years and $260 million from the Colorado Rockies earlier this year. And Rendon reportedly turned down a $200 million-plus offer already from the Nationals. So $200 million would seem to be the floor.

Strasburg doesn't have quite the profile of Cole. He is 31. He underwent Tommy John surgery in 2010. This was the first year in the past five that he made more than 30 starts and threw more than 200 innings. That said: Strasburg was incredible in October and extremely good from April through September, and the desire for frontline starting pitching and ability for every team to bid should give him a $30 million-a-year target and a six-year term. And he might get more.

Isn't that, like, in the area of $700 million combined for the three of them?

Aren't you good at math!

Don't patronize me. If three guys might get nearly three-quarters of a billion dollars among them, what exactly are players so mad about?

This is a reasonable question, and here is the answer: Massive paydays for the game's stars and crumbling job security for other classes of players don't have to go hand in hand. Most MLB teams in recent years have adopted a model in which they pay the best players exorbitant amounts, take advantage of the depressed salaries of young players and more or less eliminate the middle class that long consisted of -- you guessed it -- free agents.

The consequences of this have been monumental. A deluge of players, wanting to avoid free agency, signed contract extensions last spring. The idea of redistributing money to younger players hasn't been entirely embraced by the union, which wants younger and older players to be paid better. Salaries have not risen in line with industry-wide growth in recent years. MLB believes it's a free market correcting itself. The players just want it to stop and are livid that it hasn't.

Both sides signed this deal, right?

They did. And the players know that and kick themselves every day. How could they envision a world in which the New York Yankees and Los Angeles Dodgers would make it a priority to slide below the competitive-balance-tax threshold to reset the relatively piddly payment they make for exceeding it. This winter, it's the Red Sox who are cutting payroll and considering trading Mookie Betts.

The Red Sox are doing what?

play 2:25 What will the Red Sox do with Mookie Betts? Jeff Passan and Keith Law discuss the tough dilemma facing the Red Sox this offseason: Will they keep Mookie Betts or trade him for more pitching?

It's true. Betts, 27, the best homegrown Red Sox player since Wade Boggs, could find himself among those on the move this winter as Boston tries to reimagine itself with new chief baseball officer Chaim Bloom. The long-term deals given to Price, Chris Sale and Nathan Eovaldi saddled them with about $80 million a year devoted to pitchers of questionable health and/or production. J.D. Martinez's declining to opt out left Boston staring at a payroll that already exceeds the $208 million luxury-tax threshold if they don't make any moves. The Red Sox's farm system is a mess. One possible way to ease the strain of the former and address the latter is by dealing Betts.

Multiple executives don't believe this is a particularly practical plan. Because Betts could make upward of $30 million in arbitration this season, his trade market is already fairly limited. Beyond that, teams have shown a reticence to deal significant prospect talent for a player with only one year of club control. Winning teams would be right to do everything humanly possible to acquire a talent like Betts, but urgency hasn't exactly been a much-embraced characteristic of the game in recent seasons.

If the Red Sox are truly gung ho about dipping beneath the threshold, as two executives posited, they could do something truly wild, like a 2.0 version of the Adrian Gonzalez trade. If there were a team that wanted an elite shortstop, might the Red Sox be willing to deal Xander Bogaerts and send along Price and Eovaldi and the $147 million remaining on their deals? It's unlikely, but it would free up the Red Sox to re-sign Betts and build around him and Rafael Devers. If the Red Sox's farm weren't so grim, the notion of having to deal Bogaerts to dump contracts would be laughable. But as the Red Sox face this financial mandate, it's the sort of thing that at least will be discussed.

Who else could move?

The biggest names are Francisco Lindor and Kris Bryant. The Indians control Lindor, their superlative shortstop, for two more seasons, and while a trade this winter is not necessary, they recognize that after the July 31 trade deadline next year, the same thing that happened to Betts' trade value will happen to Lindor's. Ditto Bryant, the Chicago Cubs' third baseman whom opposing executives believe would return the most if the team's roster overhaul included some of its best players.

play 1:58 Will Francisco Lindor and Kris Bryant be traded? Keith Law and Jeff Passan predict whether the Indians and Cubs will make moves this offseason involving stars Francisco Lindor and Kris Bryant.

These aren't exactly the same scenarios. The Indians are a small-market team. They struggle to attract fans despite three consecutive division titles and a 93-win season this year. Lindor could demand a $300 million-plus deal as a free agent. If Cleveland refuses to saddle itself to that sort of commitment -- whatever the merits of that choice, it's the reality ownership has foisted on the team -- then dealing Lindor this winter actually makes sense. It would hurt. It would presumably make the team worse now. But it also could replenish the Indians for the next wave.

The Cubs' situation is trickier. They don't need to move Bryant nor his salary. Their clubhouse has grown stale over the past three seasons, and while new manager David Ross hopes to address that, the mixture of players might need a rejiggering. Bryant is an option to get dealt. Catcher Willson Contreras has significant value. Because shortstop Javier Baez is seen as the best option to sign a long-term deal, he's unlikely to go anywhere.

So if the Red Sox, Indians and Cubs are all considering trading stars ... who exactly is trying to win?

Nearly every executive and agent points westward: to the Los Angeles Angels. They have let it be known they plan to spend aggressively. They want to put together a competitive team for new manager Joe Maddon. They want to take advantage of Mike Trout's still-prime years. They're getting Shohei Ohtani back to play both ways next season. It sounds like the right time.

There are, of course, some issues. The fallout of pitcher Tyler Skaggs' death is the subject of an open federal investigation. General manager Billy Eppler is in a lame-duck year. And if they want to compete, the Angels are going to need a lot more than Gerrit Cole.

play 1:56 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.

What other teams am I going to be hearing about?

In terms of teams expected to be busy, in no particular order: the Los Angeles Dodgers, Texas Rangers, Philadelphia Phillies, San Diego Padres, Cincinnati Reds, Chicago White Sox and Atlanta Braves. Can't ever count out the New York Yankees. And if the Yankees are in it, you know the New York Mets aren't far behind. The champion Nationals are going to have some work to do, too.

What other names am I going to be hearing a lot?

Almost every team loves Zack Wheeler. He is 29 and throws very hard, and a number of teams believe they can get more out of him than the Mets did. For the teams that either can't compete in the Cole/Strasburg stratosphere or don't want to, Wheeler is the prize.

After Rendon, the most productive free agent shares a position with him. Josh Donaldson turns 34 on Dec. 8, the first day of the winter meetings, and that is the only thing separating him from a megadeal. He was magnificent in Atlanta this year -- a monster at the plate (.270/.402/.556 in the second half) and at third base. He's not going to get a six-year deal. But he warrants at least $25 million a year for three or four seasons.

Get the best of ESPN sent to your inbox The ESPN Daily delivers the biggest sports news and moments every weekday. Sign me up! Email:

Yasmani Grandal eschewed a big multiyear deal last year and wound up signing with Milwaukee for $18.25 million. He hit like he always has hit: lots of power, lots of patience, solid from both sides, extremely valuable. What's odd is how divergent FanGraphs and Baseball-Reference are on his 2019 season. FanGraphs had him worth 5.2 wins above replacement, B-R less than half that, all because of divergent opinions on his defensive value. Find a team whose metrics agree with FanGraphs' and you'll find the team that wants Grandal.

Who is the most fascinating free agent beyond the big three?

Madison Bumgarner has been so good for so long, it's easy to lose appreciation of what he has been and what he might become. In a lot of ways, Bumgarner's career numbers mirror those of another left-hander who signed a long-term deal before his age-30 season: Jon Lester. Bumgarner comes with more mileage than Lester and didn't have nearly the same walk season, but the stuff itself is very similar. Lester's fastball velocity going into free agency: 91.8 mph. Bumgarner's last season: 91.4 mph. Lester's cutter: 87.8 mph. Bumgarner's slider: 87.3 mph. Both throw a looping curveball and a changeup, too.

Does this mean Bumgarner is in line for a six-year, $155 million deal like Lester? No. But the idea that Bumgarner is some diminished version of himself is ludicrous. His 207⅔ innings last season illustrate that, as do his 203 strikeouts and nearly 5-to-1 walk rate. All that from the best pitcher in World Series history? That should play.

Honorable mention: Jose Abreu. He's exactly what new-age teams don't want: a 33-year-old right-handed-hitting first baseman who doesn't walk. He also hits the ball extremely hard, among the top 20 in overall exit velocity, as well as percentage of hits barreled. His market is worth watching, if only to offer some insight into teams' willingness to look beyond age and position.

How about a sneaky, under-the-radar guy?

How about three? Jake Odorizzi is extremely athletic, productive, intelligent and, at 29, still young. He should do very well in the market. Rich Hill is extremely unathletic but also productive and intelligent. He'll turn 40 next March, but when he pitches, he's really good. Last year was a lost year for Alex Wood. In the previous three, he was excellent for the Dodgers. At 28, he's also one of the youngest players in the class, which should benefit him greatly.

That wasn't very under the radar, you know?

You're kind of obnoxious. Fine. Here's a list of guys who have fallen off radars or never were on them in the first place who should be popular this winter. In alphabetical order: Alex Avila (hard-hitting, platoon catching option), Trevor Cahill (teams love his heavy-spin curveball), Jason Castro (see Avila), Scooter Gennett (high reward, low risk), Wade Miley (two straight really good years), Michael Pineda (stuff looked excellent before PED suspension), Rick Porcello (many R&D departments believe they can fix him), Eric Thames (legitimate, non-2019-ball-related power).

And here are three more who are totally off the radar: Yoshitomo Tsutsugo, Shogo Akiyama and Josh Lindblom. Tsutsugo, 27, is a power-hitting, on-base-getting, left-handed hitter from Japan with some defensive questions. Maybe he's a left fielder, maybe he's a first baseman, but the expectation is that his bat will play somewhere. Akiyama, who will be 32 in April, is a center fielder whose bat doesn't rate with Tsutsugo's but whose ability to play center should land him a job somewhere.

Lindblom, the former Dodgers reliever, has spent the past three seasons excelling in Korea. He's 32, and while scouts question whether his fastball will play against major league hitters, a number of analytics groups like the spin numbers on his off-speed pitches and believe he'll be a contributor somewhere in 2020, whether at the back end of a rotation or in a bullpen.

Why haven't you mentioned a single major league reliever?

Uhhhh ... it's not the greatest position. There are worse -- Didi Gregorius is legitimately the only everyday shortstop, and the outfield depth (Castellanos, Marcell Ozuna, Brett Gardner, Corey Dickerson, Yasiel Puig, Hunter Pence) is thin -- but the relief pitchers available are not going to be bank breakers, by any means.

The list: Will Smith, Will Harris, Daniel Hudson, Dellin Betances, Drew Pomeranz, Chris Martin, Joe Smith, Steve Cishek, Brandon Kintzler. There are others. Certainly someone not named here will sign for cheap and turn into a productive member of a bullpen, maybe even a closer. But as for those who have the standing to seek multiyear deals? It's not a long list.

What's the strongest position then?

There are a few choices:

Third base offers two elite-level talents (Rendon, Donaldson) and another (Moustakas) who warrants more than a one-year deal after signing for just that in each of the past two offseasons.

Catcher: There isn't quite the frontline talent, but Grandal, Castro, Avila, Travis d'Arnaud, Robinson Chirinos and Martin Maldonado, among half a dozen others, is a good start.

Starting pitching: This is the real answer. Cole, Strasburg, Wheeler, Bumgarner, Ryu, Odorizzi, Keuchel, Miley, Hill, Pineda, Porcello, Wood. And that's just the start: Cole Hamels, Kyle Gibson, Brett Anderson, Jordan Lyles, Homer Bailey, Tanner Roark and Adam Wainwright are available, too.

What comes first?

Well, first technically happened already. Strasburg opted out. Aroldis Chapman, Jason Heyward, Yu Darvish, Kenley Jansen, Jake Arrieta, Elvis Andrus and Rusney Castillo did not. Grandal and Moustakas declined their ends of a mutual option. Teams declined their options on Edwin Encarnacion, Ryan Zimmerman, Starlin Castro, Jason Kipnis and Jedd Gyorko. They exercised their options on Anthony Rizzo, Corey Kluber, Nelson Cruz, Sean Doolittle, Jose Quintana, Starling Marte, Yusmeiro Petit, Adam Eaton and Chris Archer.

Now comes the waiting, but maybe not waiting too long. The talking but maybe not talking too much. The dominos lining up, knowing what they're worth and sticking to it -- and the teams doing everything they can to knock them off that price. Trades are being discussed at all hours, and 99% of conversations go nowhere, but that 1% ...

That 1%, and the knowledge that most of these players will get signed, sustains those who do still look forward to the offseason. Admittedly, it's going through a rough patch. Used to be wired. Now pretty tired. But it's not unsalvageable, not with Cole and Rendon and Strasburg out there, not with the names being mentioned in trade talks.

It's not the NBA. It's not the NFL. It's just baseball, stuck in a system of its own creation.