By Matt Rappa, Sports Talk Philly editor 
Last spring training, Philadelphia Phillies Managing Partner John Middleton was seen chatting, signing autographs, and strolling "up and down the left-field line" with well-known agent Scott Boras.
The two were just coming off of a then-exciting deal that brought Boras' client, Jake Arrieta. to the Phillies. Middleton said he had the right-hander's name circled "years ago" among the list of prospective 2018 free agents.
When asked who he has circled among the 2019 free agent class, Middleton replied,"Oh, that's a conversation for another day. But trust me, [the names] are circled, and they have been discussed for quite a while internally."
Boras remarked that Arrieta's arrival made the Phillies "a prime destination for future free agents." Well, the free agents of the future at the time of Boras' statement are now the free agents of today. And one free agent in particular — his superstar outfielder client Bryce Harper — may just be who Boras was referring to.
"I was in spring training last year when Arrieta signed, and Scott Boras seemed to be pretty good buddies with John Middleton," MLB Insider Jerry Crasnick said Friday evening on SportsRadio 94 WIP. "They were spending a lot of time hanging out together. Scott’s a pretty smart guy, and he might have already been planting the seeds then, I think, for Bryce Harper."
Crasnick said the Phillies' moves at the 2018 trade deadline — acquiring veteran players like Jose Bautista, Asdrubal Cabrera, Aaron Loup and Wilson Ramos — shows how Middleton is "just one of these guys who says, ‘let’s do stuff, and I have money burning a hole in my pocket.’"
Read: Report: Phillies, Middleton to Pursue Signing Both Harper, Machado
Middleton may not only want to work with his "buddy" in Boras, but also Dan Lozano, agent to superstar SS/3B Manny Machado.
"The whole dynamic is fascinating. … People don’t know Dan Lozano as much, but he got Albert Pujols a $240 million contract, and Joey Votto a $225 million deal," Crasnick said.
"So, I think there’s a little dynamic between those guys of ‘hey, who’s going to get the biggest deal for each one of their guys?’"
The free agent market, per Yahoo Sports' Jeff Passan, is believed to be "robust," with "a number of free agents" possible to sign early — a contrast of last offseason's historically slow signing period. Given their spending flexibility, the Phillies will surely be part of most conversations.
"[Harper and Machado are] amazing talents. They’re both in the '26 range' age-wise," Crasnick said. "You just don’t see that. Most of these guys come out and they’re 29, 30, 31 years old. That’s going to add years to their deals.
"I have to think both of the agents are going to be looking at least a decade on these contracts."
