Jeff Passan ESPN 15 Minute Read

Cole, Rendon are the crown jewels of 2020 free agency Rick Sutcliffe tabs Gerrit Cole as his top pitching free agent, and Anthony Rendon as his favorite bat hitting the open market.

The final game of the 2019 regular season is barely a month away. The World Series starts three weeks later. It ends early enough that players will be able to file for free agency in October. And thus will begin another baseball winter -- one primed to drag on deep into the spring, just like the last two.

Major League Baseball's offseason shows no signs of changing, at least not according to more than a dozen executives and agents with whom ESPN spoke to forecast the offseason ahead. Get used to the hot stove spitting out BTUs like it's out of gas and the pace of free-agent action mimicking a Yankees-Red Sox game, they said.

This is the new normal, the consequence of a collective bargaining agreement finally past its halfway point and indisputably tilted toward the teams. The imbalance colors the game's entire economic landscape. Little incentivizes clubs to act early in free agency. The degradation of the market for older players is practically codified. It is a perfect storm of meh.

Maybe all the pent-up action left over from the winter meetings in Las Vegas last year will spill into this year's incarnation in San Diego and do something to enliven what should be one of MLB's most exciting times of the year. Likelier, the executives and agents believe, is more of the same.

So what, exactly, does that look like? We decided to play a little game of 20 Questions, baseball-style, that covers the most important free agents, potential trades, contract extension possibilities and other potentially conflagrant issues.

Who is the best free agent this winter?

Houston Astros right-hander Gerrit Cole. He is everything teams want in a front-line starter. Young (29 next month). Durable but not overused (on pace for his third consecutive 200-inning season but with just 1,146⅓ career innings thus far). Injury-free (no Tommy John scar on his elbow). Front-line stuff (especially the 97 mph fastball and wicked 89 mph slider). Ace performance (an AL-best 2.75 ERA with 238 strikeouts against 40 walks in 163⅔ innings).

Teams that want Cole understand that he's getting more than $200 million this offseason. How much more is the question. The record deal for a starter is David Price's $217 million. The record per year for a pitcher is Zack Greinke's $34.4 million (or, for the pedants who factor in the price of deferred money in Greinke's deal, Justin Verlander's $33 million). Cole seeking Price's seven years at Greinke's average annual value is not out of the realm of possibility, not with the Astros, New York Yankees, Philadelphia Phillies, Los Angeles Angels, Chicago White Sox, St. Louis Cardinals, Chicago Cubs, San Francisco Giants and Atlanta Braves all positioned and motivated to explore adding Cole.

OK: Who's the best position-playing free agent this winter?

Mark Goldman/Icon Sportswire

Washington Nationals third baseman Anthony Rendon. He's in the midst of his best season, which is saying something because for the two years prior he was one of the two or three finest third basemen in the league. This season he has gone into overdrive: a .329/.407/.617 line, his typically excellent (and underappreciated) glove, his always-stellar baserunning. The best way to describe Rendon is: He's just really, really, really good at baseball.

And as someone who is that and hits free agency at 29, he's really, really, really going to get paid. As with Cole, the floor is $200 million. The goal is presumably higher -- something in the range of the eight-year, $260 million extension fellow third baseman Nolan Arenado signed with the Colorado Rockies this spring.

Guess who represents Cole and Rendon?

And Hyun-Jin Ryu. And Stephen Strasburg. And J.D. Martinez. And Nicholas Castellanos. And Dallas Keuchel. And Mike Moustakas.

Get used to hearing Scott Boras' name again. His ubiquity will be particularly acute this winter due to his agency negotiating on behalf of the two best players in the class and a litany of others expected to get paid.

Boras also has the clearest predilection among agents to let free agents stay jobless deep into the winter. He did it last year with Bryce Harper. He has done it plenty of times before -- both successes and failures. There's no compelling reason to believe he won't do it again, not after staying strategically steadfast even as the market clearly shifted.

What are some other big stories we'll be hearing about?

Chicago Cubs manager Joe Maddon entered this season a lame duck, and the team has done little to convince those around the sport that the organization will bring him back next season. Unless, of course, the Cubs win the World Series, which at this point feels like a long shot. Mickey Callaway's long-term status as New York Mets manager remains an open question. The San Francisco Giants will be looking for a new manager too, after Bruce Bochy's retirement. The expected sale of the Kansas City Royals could prompt changes. The Pittsburgh Pirates could undergo a refresh. Abject underachievement with a club-record payroll, as is the Colorado Rockies' truth this season, doesn't bode well for long-term security.

Oh, and a number of executives are expecting monster names to be in trade talks.

Wait. Did you say monster names?

Are Mookie Betts, Francisco Lindor and Kris Bryant monster enough?

Really?

Yup. Now, this does not mean all three -- or even any of the three -- will be traded. But in preparing for this winter, rival executives believe the Boston Red Sox, Cleveland Indians and Chicago Cubs are willing to at the very least listen on their stars.

This is nothing new for any of the three organizations. All are successful in part because they have no sacred cows, because they explore all avenues to winning, because to dismiss an idea outright is antithetical to teams that pride themselves on curiosity and creativity.

Listening on all three makes total sense. For the Red Sox it's the clearest no-brainer. Betts is a free agent after the 2020 season. He has shown no desire to give the Red Sox a hometown discount, as is well within his rights. The conversation for the right fielder is likely to start at $300 million. The Red Sox are in a tight spot financially with nearly $80 million a year committed to Chris Sale, David Price and Nathan Eovaldi. Their minor league system is bad. Betts single-handedly could reload the farm. Of course, Boston also would be dealing a homegrown star -- something no team wants to do.

It's what makes Lindor moving less likely. He is not a free agent until after the 2021 season, meaning the Indians control his rights for two more years. The benefit of dealing him over the winter would be the price of two full seasons -- even heftier than a year of Betts. Cleveland also has a history of dangling some of its best players, including starters Corey Kluber, Trevor Bauer, Carlos Carrasco and Shane Bieber, to gauge their worth. Bauer was dealt at the trade deadline this year, with a year and a half to go before his free agency. The Indians may listen, but it's difficult to imagine them dealing Lindor before seeing how they perform in 2020 -- even if they know they won't re-sign him.

Bryant is the wild card. A not-uncommon feeling inside the Cubs organization is the need for a big shake-up. Perhaps Maddon leaving would provide that. The sentiment among some extends to the players too. And with Javier Baez a reasonable bet to stick around -- more on that later -- and Bryant a Boras client more prone to testing free agency, the Cubs may see him as a combination of Betts and Lindor: a star with two years of control primed to hold out for free agency but capable beforehand of enriching a farm system in desperate need of help after years of dealing away its most valuable pieces.

In baseball, trade talks are quite often nothing more than idle chatter. When they get reported -- Team X has talked with Team Y about Player Z -- they are often blown up by those who know no better. So let this be your forewarning: There are going to be talks about big-name players this year, because smart teams consider their options. That doesn't mean any of them are going anywhere. But talks can lead to offers and when the offer stage of discussions arrives, that's when you know to take them more seriously.

Back to free agency: What will the market for Madison Bumgarner look like?

It should look really good. The closest comparable to Bumgarner in a number of ways is Jon Lester. Both are left-handed. Both had fastballs top out in the mid-90s but live at the lower end. Both have been incredibly durable, incredibly clutch in the postseason and incredibly consistent in everything from their release points to their performance. Lester's career ERA+ (a metric that measures him against the league with ballparks factored in and every number above 100 his percentage better than average) is 121. Bumgarner's ERA+: 121.

Bumgarner, who just turned 30, is even a year and change younger than Lester was when the Cubs gave him a six-year, $155 million contract. It's worth noting Lester was coming off a career year, whereas Bumgarner's resurgence with the Giants -- on pace for 200-plus innings with strikeout and walk rates better than his career level -- has been much more under the radar.

Because Bumgarner has been pitching in the major leagues since age 19, the fear of wear and tear among teams considering investing in him is real. There are other free-agent pitchers: the front-line guys, right-handers Zack Wheeler and Jake Odorizzi, lefties Cole Hamels, Dallas Keuchel and Wade Miley. Bumgarner is Bumgarner, though, and the bet will be more on just how well he can replicate a past that is so very good.

Will Strasburg opt out of the remaining four years and $100 million left on his contract?

Ooooh. This is a good one.

Why to opt out: His stuff remains electric. Analytically inclined teams believe there's even more there -- that they can draw the true greatness out of Strasburg similar to what Houston did with Cole and Verlander. In a five-and-fly era, he is almost always good for six innings and quite often more.

Why not to opt out: He's 31. He threw more than 183 innings once in his first nine major league seasons. He's entering the ninth year of a reconstructed elbow, which doctors believe have finite shelf lives.

Instinct says he opts out -- or, perhaps even likelier, the Nationals, sensing that and not wanting to lose Strasburg, tack on a few more years to his current deal and invalidate the opt-out he holds following the 2020 season.

How about J.D. Martinez?

He's got $62.5 million left over three years if he does not opt out. He also can opt out following the 2020 season if he stays this winter. Considering Martinez's age (32) and position (designated hitter), the instinct leans toward not opting out. On the other hand, Martinez's sizzling August has his season line at .313/.387/.571. Only six players in baseball have a better OPS. And a guy with that sort of productivity can't get more than $62.5 million guaranteed?

And Aroldis Chapman?

The belief around baseball is that, as Ken Rosenthal reported a month ago, Chapman is as good as a free agent. Which makes complete sense. Even with slightly diminished velocity, Chapman, 32 in February, is owed just $30 million over the final two years of his deal. And if Craig Kimbrel can misread the market, sit out for a couple months and still guarantee himself $43 million, then Chapman, coming off another dominant season closing for the Yankees, can beat $30 million easy.

Who has done best for himself in 2019?

Braves third baseman Josh Donaldson. He and agent Dan Lozano took a decided risk in agreeing to a one-year, $23 million deal and going the make-good route. And they've come out the other side looking brilliant for it. Yes, Donaldson turns 34 in December. But the way he has played -- hitting .260/.374/.529 with 32 home runs -- he's well within his rights to pursue a multiyear deal at a higher cost than he's making this season. The bat, the glove, the work ethic -- Donaldson is rather similar to the last player whose make-good deal went so well: Adrian Beltre.

Who's going to get the qualifying offer?

Locks to get it -- and reject it: Cole, Rendon, Bumgarner, Strasburg, Martinez, Chapman, Donaldson, Marcell Ozuna. Outside of Cole and Rendon, it will be brought up during negotiations too.

Likely to get it: Wheeler, Hamels, Odorizzi, Giants reliever Will Smith and Yankees shortstop Didi Gregorius. If Wheeler is healthy, he gets it and rejects it. Hamels may accept it from the Cubs. Odorizzi, 29, almost certainly will hit free agency. Smith, who has made less than $12 million in his career, could get $18 million or so if he accepts. And the Yankees may be wary of Gregorius accepting and, considering the luxury-tax implications of him doing so, not offer.

Ineligible to get it: Ryu, Moustakas, Keuchel and Yasmani Grandal, who received it already, and Castellanos and Yasiel Puig, who were traded.

Who may have trouble getting paid?

Even without the qualifying offer saddling him, Puig is in many ways a walking red flag to the modern executive. They try to avoid poor on-base percentages. Baserunning and defense matter, and Puig is considered substandard at both. His age saves him -- he'll be 29 in December -- from another ding but the notion that Puig is going to cash in big this winter simply is not true as of now. Perhaps a great September or postseason changes that, but Puig feels more like a one-year deal.

What does the sport-wide reliever implosion mean?

Tough to say. On one hand, relief pitching is so dreadful in 2019 that the good ones are like gifts from heaven. So the opportunity to get, say, a Chapman or Smith or Will Harris -- all of whom have been excellent this season -- sounds glorious. But then, of course, is the truth bomb that relievers are notoriously volatile. So volatile, in fact, that the possibility of Chapman or Smith or Harris blowing up in 2020 is not at all unreasonable. Which brings about the conundrum -- and a potential impasse in the relief market. The players who performed well will want to get paid for performing well. The teams, cognizant of just how capricious relievers are, don't want to double down on giving them multiyear deals. This chasm is nothing new. This winter just may be the one where it's unbridgeable.

What's the best argument in favor of teams spending this winter?

Next winter. The class of 2020-21 looks pretty brutal. The good: Betts, Philadelphia catcher J.T. Realmuto, Oakland shortstop Marcus Semien, Houston outfielder George Springer, Yankees infielder DJ LeMahieu and Angels shortstop Andrelton Simmons. The pitching class is led by Cincinnati right-hander Trevor Bauer, Yankees lefty James Paxton and righty Masahiro Tanaka, Mets right-hander Marcus Stroman and a trio of lefties: Mike Minor, Robbie Ray and Jose Quintana. The relief options are like a secondhand store.

There's also the reality that a number of the dozen listed above will sign contract extensions before reaching free agency, neutering the class even more.

So about those extensions: Are there going to be a boatload like last winter, too?

Probably not multiple billions of dollars' worth like last year. But as the end of the collective bargaining agreement approaches and players young and old try to stomach the idea of a potential work stoppage, their calculus may change. Union sources have acknowledged that the threat of a strike or lockout likely pushed a number of players into extensions last offseason and acknowledge the same may happen again this winter.

Are you gonna name names, Passan, or just tap dance around the good stuff?

For a disembodied inquisitor, you're awfully demanding.

Let's start with Cubs shortstop Javier Baez. There has been momentum in the past to keep Baez, 26, in a Cubs uniform well into his 30s. With Baez two years from free agency, it's the sort of deal that makes a lot of sense.

With around $110 million committed to payroll next season, no massive arbitration raises and some likely non-tenders, the Phillies have every reason to pursue a long-term deal with Realmuto. He is 28. He is a leader. He is a well-above-average hitter and even better defensive catcher. He deserves a nine-figure extension.

It may be time for the Yankees to do what has seemed inevitable for years: lock up outfielder Aaron Judge. He is arbitration eligible for the first time this season and in line for a massive raise. Working in the team's favor: Judge is not due to hit free agency until after the 2022 season, when he'd be 30.

The Yankees also could pursue an extension with Gleyber Torres, who, if Gregorius leaves, is their shortstop heir. Torres, 22, won't hit free agency for another five seasons, so an extension could be preemptive -- or could approach $100 million for him while saving tens of millions for the team. Also in that camp: Red Sox third baseman Rafael Devers, who is Torres' age but due to reach free agency just after his 27th birthday.

Other names to keep an eye on: Trea Turner, Yoan Moncada, Willson Contreras, Lucas Giolito, Shane Bieber, Mike Soroka, Luis Castillo, Matthew Boyd, Jack Flaherty, Dakota Hudson and Brandon Woodruff, among many others.

Well, who isn't getting extended?

It's always smart to start with Boras. The six-year, $120 million extension this March for Xander Bogaerts with Boston was the exception, not the rule. Among Boras' young and talented clients: Dodgers outfielder Cody Bellinger, Nationals outfielder Juan Soto, Rangers outfielder Joey Gallo, Phillies first baseman Rhys Hoskins, Mets outfielder Michael Conforto, Pirates first baseman Josh Bell, Dodgers shortstop Corey Seager and Padres pitcher Chris Paddack.

Others: It's probably too early for Fernando Tatis Jr. and Vladimir Guerrero Jr. The Mets could try to lock up Pete Alonso but may want to see another year. (Though Jeff McNeil is an interesting possibility.) It's tough to see Walker Buehler agreeing to the sort of below-market deals that are the norm for pitchers -- especially with what Cole is about to get. And as for anyone from the class of 2021-22 ...

Yeah, what about the class of 2021-22?

If you see a big smile on a general manager at any point over the next two years, it's fair to wonder if he's thinking about the free-agent class of 2021-22. While it's something of a fool's errand to try to project out a free-agent class more than two years in advance, the names are titillating enough to at least say them out loud while they're still a possibility.

The Cubs alone have Baez, Bryant and Anthony Rizzo on expiring deals that winter. Freddie Freeman's contract with Atlanta is up. So are Conforto's and Tommy Pham's. The pitchers are a who's who -- more wizened than one might like but still name after big name: Verlander, Kluber, Max Scherzer, Clayton Kershaw, Zack Greinke and the young buck, Noah Syndergaard.

It's the shortstops, though, that make 2021-22 special: Baez, Lindor, Seager, Carlos Correa and Trevor Story, all due to hit free agency in the same year. It's an unprecedented group of talent for one position. And if three or four or somehow all five of them reach free agency together, it's the sort of winter that could cause tectonic shifts in the sport.

Why are we talking two years in the future when there are players who may get traded this offseason?

Because we know disembodied inquisitor will take us back exactly where we need to be. Beyond Betts, Lindor and Bryant, there are a number of stragglers from the 2019 trade deadline who could find themselves moved in the winter:

-- Starters: Ray (plenty of reason to do it as Arizona rebuilds on the fly) and Minor (less likely but still reasonably so)

-- Relievers: Edwin Diaz (the Mets want to salvage something), Kirby Yates (Padres may sell high), Ian Kennedy (as the Royals shift into prospect-hoarding mode), Alex Colome, Mychal Givens

-- Infielders: Whit Merrifield (ibid. Royals), Luis Urias (as the Padres try to land a top starter), Dee Gordon (as the Mariners whittle their payroll)

A few individual names worth noting:

-- Kluber: The Indians have a $17.5 million option with a $1 million buyout. It's an interesting conundrum. The least likely scenario is they buy out Kluber. Even after a down year, what amounts to a one-year deal with another club option for 2021 is near-impossible to turn down. Once he's under contract, though, Kluber could become a very interesting trade chip. Not as interesting as he would be coming off a strong year, but enough for the Indians to strongly consider dealing him.

-- Syndergaard: If he keeps pitching like he has in the second half -- 54⅓ innings, one home run, 12 walks, 55 strikeouts, 1.82 ERA -- he will command an immense amount on the trade market. This is the Thor the Mets have been waiting for -- one so good he might have pitched himself off the trade block.

-- Felipe Vazquez: The Pirates need talent, and whether it's a rebuild on the fly, a partial teardown or a full, to-the-studs reimagination, dealing Vazquez is a good first step when the division may be an unrealistic goal for the first few years of his contract, when he's at his most valuable. Nobody stepped up at the trade deadline this year with an offer to the Pirates' satisfaction. Perhaps this winter will be different -- in at least one way.