The Hottest Questions of the 2014-2015 MLB Offseason

Major League Baseball's offseason has just begun, and already there are all sorts of rumors and speculation—and questions—surrounding a number of free agents and trade candidates.

What better way to take the temperature of the hot stove than by running through a batch of the hottest questions to cover the latest potential transaction action across the sport?

See, that's a question in and of itself, although the six to follow are a bit more meaningful. Promise.

Which Top Free-Agent Pitcher Will Sign First?

Marcio Jose Sanchez/Associated Press

The crux of this offseason's free-agent market comes down to three starting pitchers who are being billed as a top-tier trio: Max Scherzer, Jon Lester and James Shields.

So which of the three is going to sign first and set the market for the other two?

As is, Scherzer and Lester really should be separated a bit from Shields, who isn't a true No. 1-caliber starter like they have been. The former Kansas City Royals right-hander is not only older than Lester by nearly two years and Scherzer by three, but he also lacks their ability to dominate consistently.

That means it might behoove Shields to wait things out until at least one, if not both, of the other two are inked. That way, the teams that don't land Scherzer or Lester will have to turn their attention to Shields, thus creating a market filled with a few desperate clubs for the clear No. 3 pitcher available via free agency.

A key factor with Scherzer, meanwhile, is that his agent Scott Boras is known for waiting as long as necessary to get his clients top dollar. Given that the 2013 AL Cy Young winner turned down last winter's $144 million extension offer from the Detroit Tigers, expect Boras to do just that to get more this time around.

That leaves Lester, who looks to be in line to sign first given all of the above, not to mention the lefty also is the only one of these three who isn't attached to draft-pick compensation—he was ineligible for a qualifying offer because he was traded midseason—which makes Lester a less complicated signing.

Regardless, expect some action on this front by the winter meetings, held Dec. 7-11 in sunny San Diego.

Who Is the Favorite to Land Cuban Star Yasmany Tomas?

Chung Sung-Jun/Getty Images

Given the dearth of big names on the position player front, there's a good chance Cuban defector Yasmany Tomas will score a rather hefty contract pretty soon.

Also in Tomas' favor is the fact that he'll turn only 24 years old on Nov. 14 and is considered a power hitter at a time when that trait is something all teams are chasing. But which one is the front-runner for his bat?

The latest report is that he worked out for the Arizona Diamondbacks on Monday, per his agent Jay Alou, and surprisingly did so not in the outfield but at third base. Hmmm.

A number of clubs have held sessions with Tomas, some even more than one, like the San Diego Padres. Other teams that either have a particular need for a corner outfielder with pop or have been mentioned as interested in Tomas include the New York Mets, Detroit Tigers, San Francisco Giants, Chicago Cubs and Texas Rangers.

The Philadelphia Phillies, however, are considered the No. 1 contender in the Tomas sweepstakes, especially after general manager Ruben Amaro Jr. flew to the Dominican Republic to scout him personally, according to Andy Martino of the New York Daily News. Indeed, they are "all over" Tomas, as Jon Heyman of CBS Sports reports.

That makes sense because the Phillies are badly in need of getting younger and finding some exciting players as their one-time great position player core—Chase Utley, Jimmy Rollins and Ryan Howard—continues to age and decline.

Will Japanese Ace Kenta Maeda Be Posted?

Ezra Shaw/Getty Images

Masahiro Tanaka's posting and bidding war was one of the biggest storylines to follow last winter, and there could be another top Japanese arm coming over again.

As Doug Miller of MLB.com writes: "This year it's possible that we'll see another Japanese righty, Kenta Maeda, enter the posting process. Maeda reportedly doesn't possess the raw stuff of Tanaka, but he's only 26, and he has compiled a career 2.43 ERA in Nippon Professional Baseball."

The last report on whether the Hiroshima Carp would be making the right-hander available to MLB indicated it was unlikely, according to the The Japan Times.

"We have the right," team owner Hajime Matsuda said in mid-October of Maeda's potential posting. "We would like to let him go, but based on his production this year it will be difficult."

In fact, Maeda isn't eligible for free agency until the 2017 offseason, so he does require the Carp's blessing, if you will. He has made it known that he wants to pitch in America.

Remember, under the rules between MLB and NPB established a year ago, the maximum release fee a Japanese club can gain for a player is $20 million. So it's really a question of whether the Carp want that money now or if they prefer to keep their star for another year or two and potentially risk major league teams losing interest as Maeda gets closer to 30 years old.

Execs and players could get a first-hand look at Maeda during the upcoming All-Star Series in Japan, which has games between MLB and Japanese stars scheduled from Nov. 11 through Nov. 20.

Are the New York Yankees Really Not Going After the Biggest Names?

Carlos Osorio/Associated Press

One of baseball's biggest spenders might be shopping in the bargain bin for a change.

Here's what Mark Feinsand and Bill Madden of the New York Daily News wrote about the New York Yankees' offseason plans:

"

After spending more than $450 million last winter on Tanaka, Jacoby Ellsbury, Brian McCann and Carlos Beltran, the Yankees aren't looking to add any more $100 million deals to their payroll, which ranked second behind the Dodgers last season, taking Scherzer, Lester and Shields out of play.

"

Also out of play, presumably? Infielders Pablo Sandoval and Hanley Ramirez, both of whom could fetch nine figures on the open market.

Granted, the talk surrounding the Yankees this time last year was that they were driving hard to get and stay under the $189 million luxury  tax threshold, and then they blew that plan up by handing out massive money as spelled out above.

That makes Craig Calcaterra of Hardball Talk, for one, skeptical about this news: "The Yankees have a long and rich history of saying they aren’t interested in this or that player or that they have no plans to exceed this or that figure in their budget, only to go ahead and drop serious cash anyway. So take all of this with a grain of salt."

If it is true, though, and if the franchise focuses its efforts on mid-market options like Chase Headley, Brandon McCarthy, Andrew Miller and Asdrubal Cabrera or Stephen Drew, this would have a ripple effect on the market by taking leverage away from agents looking to use the Yankees to drive up their client's price.

What's Next for the Chicago Cubs?

Gene Puskar/Associated Press

Folks, the Chicago Cubs are relevant again. Not only relevant, they've become the talk of the sport recently, what with the hiring of revered skipper Joe Maddon and a burgeoning core of talented prospects and young big leaguers.

But with Maddon in tow, what do the Cubs do next?

Lacking in quality starting pitching, they could target a top-of-the-rotation arm like Scherzer or Lester via free agency. While Lester has been linked to Chicago in part because of his ties to president Theo Epstein and GM Jed Hoyer from their time together in Boston, signing Scherzer would cost only a second-round draft pick, since their first-rounder is protected by virtue of being one of the top 10.

There's also the possibility of trading for an elite pitcher like Cole Hamels of the Philadelphia Phillies, as Jon Heyman of CBS Sports suggests. Remember, the Cubs claimed the left-hander on waivers late in the season before the Phillies pulled him back, so the interest is there, as is the need.

"I have a good feeling the front office is looking to add one of the big arms at the front of the rotation," righty Jake Arrieta said Tuesday via Mark Gonzales of the Chicago Tribune. "That would be the next step, especially after adding Joe."

It could be, but there's also the chance Chicago instead goes after Russell Martin, as Heyman reports. That would both provide an upgrade at catcher and infuse veteran leadership into a club that will require some as the youngsters start churning through.

Martin, who was one of only four players with at least 400 plate appearances to post a .400 on-base percentage in 2014, helped turn around the long-suffering Pittsburgh Pirates.

Epstein and Hoyer are in a good position thanks to the young core of position players they've constructed. It's now up to them to decide which way to go and what move to make next.

Can the Philadelphia Phillies Really Trade Ryan Howard?

Matt Slocum/Associated Press

Buster Olney of ESPN (subscription required) posed this very question, and boy, is it a doozy.

Perhaps more than any other organization in baseball, the Phillies are badly in need of a teardown. Nothing would signify that more so than unloading first baseman Ryan Howard, even if it means eating the vast majority of the $60 million the soon-to-be 35-year-old is owed through 2016 to get it done.

Olney continues:

"

There is another factor working against the Phillies in their effort to move Howard: The market is currently saturated with DH types. Victor Martinez is the best available, followed by the likes of Nelson Cruz, Billy Butler, Mike Morse, Delmon Young, Kendrys Morales, Corey Hart and others. The Braves are said to be open to moving Evan Gattis, an excellent (and cheap) DH candidate with far less mileage than someone like Howard.

[...]

Look, no matter how the Phillies do it, they’re going to have to be very creative to move Howard. But rival officials are convinced that Amaro will do whatever it takes to move the slugger this winter—especially because Howard’s 10-and-5 rights to reject deals will kick in next summer.

"

Sounds like the deck is stacked against this fantasy becoming a reality for the Phillies, as Paul Casella of MLB.com writes:

"

Considering all the circumstances, it comes as no surprise that the Phillies are working to find a trade partner. The real surprise would be finding a team that is either willing to take on those financial obligations or has a player with a similarly unfavorable contract to swap.

"

Then again, the Toronto Blue Jays once were able to swap Vernon Wells when he was declining rapidly, on the wrong side of 30 and still had nearly $90 million and four years left on his albatross of a contract. So, hey, anything's possible.

Statistics are accurate through the 2014 season and courtesy of MLB.com, Baseball-Reference.com and FanGraphs unless otherwise noted.

To talk baseball or fantasy baseball, check in with me on Twitter: @JayCat11.