Manny Machado and Bryce Harper were never supposed to be free agents all the way into spring training. There are several different reasons why things have dragged on, but among them is that Machado is represented by Dan Lozano, and Harper is represented by Scott Boras. Neither agent wanted to be the first one to sign, believing that would cede the other too much leverage. And so we had a waiting game, up until Tuesday. Tuesday, someone finally blinked, and Machado agreed to a ten-year contract with the Padres worth $300 million. In theory, that makes it easy for Boras: He’ll be looking for at least $301 million to beat Machado, if not $326 million, to beat Giancarlo Stanton. Rumors have already started flying around.

Harper’s decision point is coming, and it stands to reason it’s coming soon. With Machado signed, there’s less reason to wait. Days ago, a number of people reported Harper was close to agreeing with the Phillies for $300+ million. Now, Wednesday, we have this, from Jon Heyman:

Bryce Harper is believed to have turned down multiple offers over 300M in recent weeks. at least 5 teams are believed still in contact, tho Philly, SF and perhaps Wash appear to have more chance than SD (just gave 300M to Manny) and CWS (seemed more focused on MM) — Jon Heyman (@JonHeyman) February 20, 2019

It was widely reported that, at the end of last season, the Nationals offered Harper a $300-million extension. That’s just another reason why Boras would be trying to get something bigger. I’m not sure there’s a more prideful agent in the world. Despite everything, though, I’m skeptical there’s an actual $300-million offer for Harper on the table. My best guess is that Boras finds himself in a tricky position.

The team at the heart of this right now is the Phillies. The Phillies were connected to Machado, and they remain connected to Harper, with many people, myself included, having assumed they’d end up with one of them. They’ve been perfectly lined up to strike, with the big-league roster improving, and with other big-budget ballclubs sitting the sweepstakes out. You know about the whole “stupid money” quote from months ago. The Phillies are under public pressure to make another splash, and Boras certainly knows it. For as active as the Phillies have already been, if they miss on Harper, the fans will be…less than understanding.

We know the Phillies are still in touch with Harper. It’s the rest of the suitor pool that’s tough to figure out. Machado appeared to have the broader market. The Nationals have already made Harper a huge offer once, but they’ve also already conducted a whole offseason, and their projected outfield is solid and full. Here’s an excerpt from Brittany Ghiroli from the other day:

People in the Nationals’ organization, per sources, were told by the team’s front office this week that the team was out of the running for Harper.

The Giants have been linked to Harper of late. It’s a big-resource organization, with holes to fill, and perhaps they’re now playing the part of the Padres on Machado, trying to take advantage of a slow-developing market. And yet the Giants are also now directed by Farhan Zaidi, whose background with the A’s and Dodgers doesn’t lead one to believe he’s a fan of handing out mega-contracts. What reports there are have suggested the Giants are only interested in a shorter term. Plenty of teams would be more interested in a shorter term.

Meanwhile, it’s improbable that the Padres would give out another one of these. And the White Sox reportedly topped out at $250 million in guaranteed money to Machado. There were options and incentives that would’ve made the sum far greater, but those aren’t guarantees. An agent like Boras is looking for a guarantee.

So let’s circle back to the Phillies. We can assume that the Phillies would love to sign Bryce Harper. But where might they be today? Matt Gelb’s recent article offers some clues:

Throughout the negotiation process, two sources said, Phillies general manager Matt Klentak was adamant with Lozano: The Phillies would not go to $300 million for Machado. Lozano called again on Tuesday. The Phillies would not counter San Diego.

[…]

“If the reports are true, then this contract will exceed our valuation,” Klentak said. “Sometimes you have to be willing to walk away.”

Then this contract will exceed our valuation. It’s not the most poetic way to put it, but it’s still a significant message. With regard to Machado, the Phillies didn’t believe he’s worth $300 million. They didn’t believe he’s within what you might call the margin of error. They weren’t close enough to $300 million to just bump the offer up to seal the deal. The Phillies held firm, and they watched Machado go somewhere else. They stuck to their valuation of the player. And their valuation of Machado is almost certainly close to their valuation of Harper.

The Phillies haven’t revealed who they actually prefer. Different members of the organization might even give you different answers. This has been one of the most common questions of the offseason: Do you take Machado, or do you take Harper? In reality, though, the reason they’re hard to separate is because they’re so close. Both Machado and Harper are star players who became available as free agents at the age of 26. Here’s a comparison of their past three years, along with a next-year projection:

Player Comparison Player Age Years PA wRC+ xwOBA UZR DRS WAR WAR/600 2019 WAR/600 Manny Machado 26.6 2016-2018 2095 125 0.369 6 12 15.1 4.3 4.8 Bryce Harper 26.3 2016-2018 1814 132 0.377 -7 -25 11.2 3.7 4.5 xwOBA from Baseball Savant. 2019 WAR/600 is a projection based on Steamer and ZiPS combined.

Yes, Harper won the league MVP in 2015. As such, he might’ve established a higher ceiling. But he hasn’t been close to that player ever since. He has still been good, absolutely. But over three years combined, Machado has been a little better. Moving forward, Machado is projected to be a little better. Harper has the more dangerous bat, but he’s also a below-average defensive corner outfielder. Machado is an above-average defensive third baseman, who can even spend some time at shortstop. Harper is good, but he might be more replaceable. Especially if he’s close to as bad a defender as he was in 2018.

When the Phillies looked closely at Manny Machado, they ran their math, and came up with a valuation under $300 million. They stuck to it in negotiations. What reason do we have to believe the Phillies’ valuation of Harper would be much higher? If anything, there’s reason to believe their valuation would be a little *lower.* And when the Phillies were challenged on their valuation of Machado, they didn’t budge. Granted, they knew then they could fall back on Harper, but they still might not feel much pressure. Even assuming the Phillies are at a number under $300 million, they could still feel as if they have the high bid.

Scott Boras wouldn’t want the Phillies to think they have the high bid. The Phillies don’t want to bid against themselves, so Boras would want to turn up the heat. It is presumably not a coincidence that so many rumors are floating around these days, trying to jolt the market. There have already been a number of reports simply assuming that Harper’s contract will be larger than Machado’s. That’s what Boras is looking for, but I also don’t think it’s something to be taken for granted. The Phillies would have to be convinced they need to go higher. I doubt they think they’ll be out-bid by the Giants. Or the White Sox, or the Padres.

The great unknown here is, and has always been, the Nationals. In so many ways, the Nationals have already moved on, and they’re set in the outfield with Victor Robles, Adam Eaton, and Juan Soto. But ownership has a long-standing connection to Boras, and it seems like convincing the Lerners to splurge is Boras’ best path forward. The Nationals seem like the most likely team to bail Boras out of this, probably by giving Harper some massive guarantee with significant deferrals. Deferrals like what Max Scherzer got, or like what Stephen Strasburg got. With the Nationals in play, Boras could get his guarantee. He wouldn’t have to lose face.

But if the Nationals are out — and the Nationals seem very possibly out — I don’t know who’s there to realistically push the Phillies. The market simply isn’t strong. Which would put Boras in an uncomfortable position, looking at less guaranteed money than what Lozano got for Machado. At that point, Boras might prefer a record average salary over a record total commitment. Whether even that would be possible, I don’t know. But Boras right now is in a tough spot. If the Nationals don’t come back around to save him, it feels like he’s going to get a blow to his ego.