MLB winter meetings: Bryce Harper, Manny Machado could sign record-breaking contracts -- whose will be bigger?

Infielder Manny Machado and outfielder Bryce Harper are generational free agents who head the current class of 2018-19. Each is going to sign for a huge sum, but the unknown particulars are what's compelling. 

To wit, who is going to sign the larger contract? And will one or both of them surpass the record $325 million pact that Giancarlo Stanton signed with the Marlins more than four years ago? 

As for the first question, most would lean Harper. After all, he's the ballyhooed of the two -- Harper has been something phenom since he was 12 or 13 years of age -- and he's the one with the MVP trophy. Before we unfurl our roundtable on this very matter, let's briefly lay out the cases for Harper and Machado to be the highest-paid player of the offseason:

The case for Harper

  • He's more than 100 days younger than Machado. Hey, they matters when we're talking about tight margins. 
  • As noted above, Harper has won an MVP. In 2015, he put up an OPS+ of 198 across 153 games. Machado has yet to reach an offensive ceiling even close to that. 
  • His career offensive numbers are significantly better than Machado's. 
  • You can argue that Harper has more star power than Machado. 
  • The controversy over Machado's inconsistent hustle might play a very small role here. 

The case for Machado

  • Machado, unlike Harper, can stick at a premium position moving forward. He's said he wants to remain at shortstop with his next team. At that position, he profiles as at least average. The alternative is third base, where he's an elite defender. Harper, meantime, is relegated to a corner outfield spot or perhaps first base. Also worth noting is that Harper's defensive numbers cratered last season. 
  • Machado, unlike Harper, didn't receive a qualifying offer. That means the team that signs Machado won't be forfeiting a draft pick or two for the privilege. To be sure, no one's going to back off a deal with Harper because of draft pick losses, but it's a factor that may be baked into his final price tag. 
  • While Machado does have a surgery on each knee in his past, he's been more durable than Harper over the last three seasons. 
  • Machado has the higher career WAR, by a margin of 33.8 to 27.4. 

Now let's discuss whether Harper or Machado winds up with the larger contract this offseason. And will either of them or both them surpass the total value of Stanton's contract? Here's what we think:  

Dayn Perry: I think it's entirely possible Machado winds up being the better investment (as noted above, he's got a higher career WAR than Harper), and teams these days are certainly prioritizing players who can produce at the plate while also manning premium defensive positions. Here's what I can't get away from, though: Harper's best single-season, as noted above, was an OPS+ of 198 (career mark of 139), while Machado has peaked at 146 (121 career mark). I think that "best hitter in baseball" ceiling is what will get Harper the bigger contract. As it's said in baseball, once you display a skill, you own it. Harper's shown he can produce at the plate at a Mike Trout level. Machado hasn't. 

R.J. Anderson: I'm on record suggesting that Machado is the better player. He can play the left side of the infield, and while his bat isn't quite as good, that defensive versatility matters a lot -- especially over 10 years, or whatever the length of these deals proves to be. Machado's perceived makeup issues are the only reason I'd hesitate in saying he'll receive more money -- but, based on value alone, he deserves it.

Matt Snyder: I don't think there's any way to come to a conclusion here analytically. It's just too complicated with the teams and agents negotiating, especially when most reporting says titans like the Yankees and Cubs won't be involved. My gut tells me the Phillies are going to offer the most money and Harper doesn't want to end up there, so it's going to be Machado. As noted, it's a total gut feeling but I don't know of any other way to decide at this point with all the market uncertainty. 

Mike Axisa: I think Harper will wind up with the bigger contract for two reasons. One, I think he's going to be the better player the next several years -- Mike Trout is pretty much the only player I would comfortably expect to outproduce Harper the next five years -- and I think most teams see it that way as well. Machado's great, don't get me wrong, but Harper is a generational talent and we saw just how good he can be during his MVP season. I think clubs will be more willing to pay Harper top dollar because of that.

And two, Harper is a Scott Boras client and Boras is the king. This is the guy who convinced the Tigers to give Prince Fielder a nine-year contract and move Miguel Cabrera to third base to accommodate him. I'll never doubt him. Boras is typically very patient with his top clients. I see him dragging Harper's free agency out into January, after Machado signs. Then, once Machado is off the board, all the teams that missed out on him (Phillies? Yankees? Cubs? Nationals?) will turn to Harper and the price will go up.

Katherine Acquavella: My guess is that Harper will sign a bigger contract than Machado, but it will be close. Boras has been marketing Harper as a "generational player" and honestly he's right. Harper is one of 14 MLB players to have hit 150 home runs before turning 25, The only active players to have done so are Albert Pujols and Trout. I see Harper as a player with more star power, who can make any team he joins immediately more marketable.

MA: As for surpassing Stanton's contract, I expect both Harper and Machado to do it. I'm not sure either guy will get $400 million, but I do expect both to get quite a bit more than $325 million -- $350 million or even $375 million seems doable to me. The thing is, both contracts are going to contain opt-outs and escalators and all that good stuff, so it'll be difficult to know what the true value of the deal is. If you're their agent, don't you have to push for an opt-out that lets them test free agency again before their 30th birthday?

KA: There is a lot of unpredictability for the free-agent market right now, and the predictions that have been made so far have put both Machado and Harper below Stanton's record deal. However, I do think that the both of them will sign a deal that surpasses Stanton's $325 million deal.

DP: For reasons laid out above, Harper breaks it, but Machado doesn't. 

RJA: I agree with Axisa. I think both will top it, but I'm not quite as certain about the $400 million mark -- even with all the tricks and treats baked into these deals nowadays.

MS: Yes, I think Machado tops the Stanton deal. I'll say Harper does, too. 

CBS Sports Writer

Dayn Perry has been a baseball writer for CBS Sports since early 2012. Prior to that, he wrote for FOXSports.com and ESPN.com. He's the author of three books, the most recent being Reggie Jackson: The... Full Bio

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