This is not a fresh conversation. It is had almost yearly around this time on the calendar.

It is the tale of super agent Scott Boras and some client and their reading of the free-agent market. Is the duo overestimating the player’s worth? Will the market eventually cave and pay the asking price? How late in the offseason might we find out?

This winter is just another edition of the debate, with Boras toting around ace Max Scherzer as his prized client, a $200 million price tag dangling from his ear. As of now, as we have come to expect with the high-priced Boras clients, there are no potential buyers and no firming up of the options.

So are Boras and Scherzer overplaying their hand? They certainly do not believe so, as Boras eluded to Insider Jon Heyman last month:

Premium free agents are rarely talked about at the GM [general manager] meetings. This is an owners’ decision. Every GM wants him. There’s always a place for him on every team. The issue is not whether the player is wanted. The issue is whether the owner will make the commitment to try to win the World Series.

That commitment is healthy. Scherzer already turned down a six-year, $144 million contract extension offer from the Detroit Tigers earlier this year, and several reports have Scherzer seeking well beyond that monetary figure. That was confirmed last week at the MLB winter meetings.

That $200 million asking price is not surprising considering the agent, but only one other pitcher in the sport has achieved that kind of money—Clayton Kershaw. For as good as Scherzer is, he is not in the statistical class of Kershaw, and there is about a four-year age difference between the two, with the Los Angeles Dodgers ace winning that bout, also.

Scherzer is considered to be better than Jon Lester, who agreed to a six-year, $155 million contract with the Chicago Cubs at the winter meetings. But is he really $50 million better? Aside from Boras, it is difficult to find anyone who thinks Scherzer is worth that much more, so it seems Lester’s deal could hurt Scherzer‘s value.

Then again, all it takes is that “One Dumb Owner” to accept the terms. Longtime New York Daily News columnist Bill Madden set forth that phrase years ago in reference to Boras always finding his mark, as he has done with guys like Mark Teixeira and Prince Fielder.

In Fielder’s case after the 2011 season, it appeared Boras overvalued his client. But when Victor Martinez blew up his knee training that winter, Detroit Tigers owner Mike Ilitch pounced on Fielder and gave him $214 million over nine years. If not for that injury to one of the game’s premier hitters, Fielder’s situation might have played out much differently.

Boras escaped embarrassment there, but we have seen his clients in the past overplay their hands and end up late in the offseason without a deal. That has forced some to settle for less than what Boras promised he could get or to be forced into one-year “pillow deals.”

Michael Bourn is the most recent example. He wanted seven years and around $80 million—or at least Boras did—when he hit free agency after the 2012 season, but Boras could only land him $48 million over four years with the Cleveland Indians. That deal wasn’t reached until days before players reported to spring training.

No one will be surprised if Scherzer‘s journey reaches February, especially because teams that can afford Scherzer are likely to exhaust every other avenue before even engaging Boras about his 30-year-old client.

The free-agent market still features James Shields, a pitcher who could command half the years and maybe less than half of the salary Scherzer is seeking. Shields is not an ace, but he is a legitimate top-of-the-rotation arm that becomes far more attractive when his demands are set next to Scherzer‘s. Once Shields does sign, Scherzer‘s suitors will become a bit clearer.

The trade market offers plenty of options, but despite being cheaper in terms of money, they will cost plenty in personnel. Cole Hamels, Jordan Zimmermann, Doug Fister and Johnny Cueto are all front-line pitchers available in trades, but their teams will be asking for plenty in return. Then again, signing Scherzer will cost a draft pick because he turned down Detroit’s qualifying offer.

Logical theories have Scherzer‘s options limited to three teams for now: the Tigers, Washington Nationals and New York Yankees. The Tigers because of Boras‘ relationship with Ilitch despite GM Dave Dombrowski saying they aren’t pursuing Scherzer, the Nationals because they could trade Zimmermann for a sweet haul before adding Scherzer‘s money and the Yankees because it’s hard to believe them when GM Brian Cashman says Scherzer is “on a higher [financial] level than we’d like to play in right now.”

All three of those teams are in win-now modes, with those windows potentially closing as their current rosters stand. So believing Madden’s one owner comes from one of those clubs is not an absurd theory.

It is also not absurd to think that, considering the markets for pitching, Boras is overvaluing Scherzer. We have seen him do it before, and we have seen him do it with an A-1 client (Fielder) only to be bailed out by an unexpected circumstance.

It is hard to bet against Boras because we have seen him nab ridiculous amounts of money for players that 29 other owners did not see worth the bounty. And if a team like the Nationals or even the Dodgers make a blockbuster trade involving one of their pitchers, they suddenly become Boras‘ obvious target.

For now, it is too early to say Boras and Scherzer are overplaying their hand. This is still typical in Boras‘ world of negotiating. However, if in a month from now we are still wondering where Scherzer will pitch, the conversation can be rehashed with a different outcome.


Anthony Witrado covers Major League Baseball for Bleacher Report. He spent the previous three seasons as the national baseball columnist at Sporting News and four years before that as the Brewers beat writer for the Milwaukee Journal Sentinel. Follow Anthony on Twitter @awitrado and talk baseball here.

Read more MLB news on