The Phillies will renew what has been at times a trying, but always interesting, relationship with baseball's most powerful agent when club leaders travel to Las Vegas on Saturday.

Somewhere in that desert town of bright lights and big shows, Phillies officials will sit across from Bryce Harper, one of the two megastars on this winter's free-agent market. The other, of course, is Manny Machado, a player the Phillies have already visited with and are actively trying to sign.

The Phillies' interest in Harper is real, but for months it has been clear that Machado is the team's priority. It is unlikely the team would sign both players and club president Andy MacPhail indicated as much back in October. If Machado signs elsewhere, the Phillies' interest in Harper could swell, hence Saturday's meeting with the player in Las Vegas. It will be the first time Phillies officials have met with Harper. They have already had several ground-laying conversations with Harper's super-agent, Scott Boras.

The current Phillies front office knows Boras well, having hammered out a deal with him for Jake Arrieta last year.

But Boras' relationship with the franchise goes back farther than that and it hasn't always been smooth sailing. Working out a deal for first-rounder Carlton Loewer in 1994 was easy, but it was a different story just a few years later when the two sides could not come to an agreement for No. 2 overall pick J.D. Drew and he re-entered the draft after a year of acrimonious negotiations that included Boras appearing via satellite from California on our very own sports network and getting into a testy verbal joust with Curt Schilling, who was then still a Phillie and sticking up for his team.

The Phillies had only limited dealings with Boras for a while after L'Affaire Drew. Things got a little sticky in the fall of 2011 when the two sides were moving toward a contract extension for free agent Ryan Madson before the Phillies quickly pivoted and signed Jonathan Papelbon. Boras was none too happy with the Phillies, but he didn't hold a grudge. He never does. He didn't become the game's most powerful agent by closing doors on potential landing spots for his guys. Heck, he even put on a happy face during the Drew saga and negotiated a one-year deal with the Phils for infielder Mark Lewis in December 1997.