By Tim Kelly, Sports Talk Philly editor 
The Philadelphia Phillies introduced RHP Jake Arrieta to the media Tuesday morning. It was the biggest signing that has been made during Matt Klentak's tenure as general manager, and organizationally since the club signed Cliff Lee prior to the 2011 season. Managing partner John Middleton told The Athletic's Jayson Stark after the press conference that Arrieta's name had been in his mind for years. When Stark followed up about next year's free-agent class, Middleton largely deflected, but did say that the top free-agents in next year's class have been circled by the team.
Next offseason, Manny Machado and Bryce Harper will headline what some believe will be the greatest free-agent class in baseball history. ESPN Insider Buster Olney appeared on the 97.5 The Fanatic morning show Tuesday, and told Anthony Gargano and Bob Cooney that he expects one of the two superstars will end up signing with the Phillies:
"Anthony, as you know, I grew up on a dairy farm in Vermont. I would bet the family farm back in Vermont that one of those two guys is going to wind up with the Phillies. Look, the Yankees, when they traded for Giancarlo Stanton, that pretty much took them out of the mix on Bryce Harper. And we know that Bryce is someone who is going to be talked a lot about next winter. And on top of that, Brian Cashman, the general manager of the Yankees, he is at the top of that list [of risk-averse general managers]. He does not like risk. People have connected Bryce Harper and Manny Machado to the Dodgers. Andrew Friedman who runs the Dodgers hates risk. The idea of a 10-year/$350 million contract is not something that those guys are going to do."
While this is a welcome development to Phillies fans, from here, Olney might be a bit off with some of his thoughts. He's correct in saying that acquiring Giancarlo Stanton this offseason likely takes the Yankees, who Olney was once was a beat reporter for, out of the Harper sweepstakes. However, he may be underestimating the amount of money that both Harper and Machado will get on the open market, while overestimating the amount of risk associated in signing the two.
Both Harper and Machado will reach the open market at age 26. A 10-year/$350 million contract would be record-setting, but it feels likely that both of the two, should they choose, could get free-agent contracts in excess of $400 million. If it becomes evident that Harper plans to re-sign with the Nationals, it could create a bidding war for Machado, pushing his price-tag closer to $500 million. Machado won't return to Baltimore, but if one team becomes the prohibited favorite to sign him, the same effect could work in Harper's favor.
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As for the risk associated in signing the two, it's probably not quite as much as one would think. While both will likely sign record-setting 10-year contracts, they will only be 26. If they play out the entirety of the contract, they'll only be in their age-35 season in the final year of their contracts. There are worse things than having a Hall of Fame talent from age 26-35. More likely than that is that Harper and Machado will opt-out of their contracts in their early 30s. With another half decade (give or take) of inflation, they will, at the very least, likely be able to get more money annually on the open market. So the real risk would come when they opt-out of their deal and the Phillies (or any other team) are left to decide on whether to give them another long-term contract.
Olney went on to guess that Harper will ultimately remain in the National League East, but re-sign with the Nationals, who made him the No. 1 overall pick in the 2010 MLB Draft. He thinks that Machado, who is very familiar with the Phillies front-office, will sign with the Phillies:
"The Phillies might be the only big market team, with a ton of payroll flexibility, who are willing to go that high. My guess is, if I were just asked to bet today, I think that Bryce Harper goes back to the Nationals and I think that Manny Machado winds up with the Phillies."
It is worth noting again that Olney is well-connected with the Yankees. It's also worth noting that his sentiments aren't what many other baseball insiders have shared.
Jon Heyman of FanRag Sports reported last month that should Machado reach free-agency next offseason, the Yankees are viewed as "practically a slam dunk in some quarters" to land his services. USA Today's Bob Nightengale added that Machado, who will play shortstop full-time in 2018, "would like to be on center stage in a big market," something echoed in Heyman's story. The Orioles inexplicably allowed Machado to get to this point without trading him – an extension was probably never realistic – and Nightengale, too, says that the Yankees are prepared to make a serious push for the three-time All-Star.
None of this is to say the Phillies should altogether write off pursuing Machado next offseason. They will be able to spend as much as any team, and they also have a strong young core developing. The problem is the Yankees have an even better core, may win the World Series this year, and, like always, will be able to spend.
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As Olney noted, the Nationals will be a factor in Harper's free-agency, unlike the Orioles with Machado. However, Heyman also reported last month that the Nationals understand that "it's not too likely that they'll be able to keep him." The Dodgers are viewed by many as the favorite to land Harper. (Olney, apparently is not one of those people.) The Dodgers, however, aren't viewed as an overwhelming favorite, like some seem to believe the Yankees are in the Machado sweepstakes.
Things can change, but the guess here is that if the Phillies sign one of the two, it will be Harper.
The Phillies, of course, would become a significantly better team by adding either of the two. That Olney, who has no connection to Philadelphia, feels this strongly that the Phillies will land one of the two blue-chip free-agents next offseason, should give you an indication of how seriously the Phillies (and Middleton's wallet) are taken around the league.
