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Bryce Harper’s agent, Scott Boras, has grown fond of the Phillies | Bob Brookover

Once again the paths of super agent Scott Boras and the Phillies have crossed. Their meetings used to be contentious. In more recent times, they've been successful. Is the biggest success of all coming soon?

Washington Nationals free agent outfielder Bryce Harper is on track to be the highest-paid player in Major League Baseball history.
Washington Nationals free agent outfielder Bryce Harper is on track to be the highest-paid player in Major League Baseball history.Read moreManuel Balce Ceneta / AP file photo (custom credit) / AP

Once again the paths of super agent Scott Boras and the Phillies have crossed.

That, in itself, is not at all unusual. For more than three decades, Boras has represented some of the best players in the history of the game and constantly been on the hunt for baseball’s next young superstar out of high school or college.

It is inevitable that at some point every team is going to have to deal with Boras, the most prominent agent in the history of professional sports.

Boras, 66, has been ranked as Forbes Magazine’s most powerful sports agent for six consecutive years. According to the magazine, he made $105 million in commissions last season and now he has his sights set on making free-agent outfielder Bryce Harper the highest-paid player in baseball history.

The Phillies, of course, would love to participate in that process and are the Las Vegas favorite to land the Las Vegas native at the winter meetings this week in Las Vegas. They’d love to have their slot machine at Mandalay Bay come up Bryce Harpers across the board, but this casino game will work in reverse with the winner likely to pay out a jackpot of more than $300 million and possibly as much as $400 million.

Those are insane numbers, but the fact that the Phillies are thinking about it has made them a lovable dance partner for Boras. That Boras and the Phillies have become negotiating companions is what makes the story so compelling.

There was a time, of course, when it seemed as if Boras would have advised one of his players to sign with a team in Siberia before sending him to Philadelphia. All right, maybe that’s a bit of exaggeration, but J.D. Drew did have to play two seasons in St. Paul, Minn. just to avoid signing with the Phillies after they made him the second overall pick in 1997.

The surreal circumstances that followed the selection of Drew remain etched in the memory of former Phillies general manager Ed Wade.

Boras tried every trick in the book and even invented some new ones in order to get Drew declared a free agent after the Phillies drafted him. The agent even tried the old bait-and-switch maneuver, protesting that the Phillies never mailed a contract to Drew’s “permanent” address after they selected him. The Phillies had sent a contract to Drew’s family home in Georgia, but Boras claimed it should have gone to the Tallahassee, Fla., address he occupied while playing at Florida State.

Wade said the Phillies even hired a private detective to photograph the contract in Drew’s mailbox, but Boras argued on in an attempt to get his client to be declared a free agent.

As the signing deadline for Drew approached, the Phillies and Boras pulled out all stops. Star third baseman Scott Rolen met with Drew and pitcher Curt Schilling assured the outfielder he’d be welcomed with open arms if he signed with the Phillies despite the turbulent contract talks. Boras tried to get the Phillies to trade Drew.

“By that point, I think we were in the ditch anyway,” Wade said. “I think Scott had already negotiated a deal with other teams.”

Drew reentered the draft in 1998 and was selected fifth overall by the St. Louis Cardinals. He signed for a reported $7 million, which was $4 million more than the best offer from the Phillies, who were steadfast about sticking within the financial guidelines Major League Baseball had established for the draft at that time.

Wade, who replaced Lee Thomas as Phillies general manager in the middle of those negotiations, still wonders what might have happened if the Phillies could have signed Drew.

“We felt like it was a great opportunity and he was a great fit into what we were trying to do,” Wade said. “All the right elements would have been in place.”

The Phillies, after failing to sign Drew, drafted Pat Burrell with the first overall pick in 1998. Neither Drew nor Burrell became superstars, but a lineup with those two, Rolen, and Bobby Abreu could have been a lot of fun to watch.

Ruben Amaro Jr. also had some contentious dealings with Boras during his time as Phillies general manager, with the most noteworthy being a heated disagreement over a failed contract negotiation with reliever Ryan Madson in 2011. Boras thought he had completed a multi-year deal for Madson, but the Phillies ended up signing Jonathan Papelbon instead.

“To be honest, I think both of us moved past that pretty quick,” Amaro said. “We had a disagreement, but you have to move on. You have to deal with it and continue to do what’s best for the club.”

Wade said there were times he would have liked to have negotiated with Boras, but the Phillies were not in a financial position to do so.

“When Scott is the agent, it is always an element of discussion,” Wade said. “You know what the track record has been and there are pluses and minuses involved with that.

"The lion’s share of the time when I was with Philadelphia we did not have the wherewithal to chase his players. I remember at the winter meetings one time, we knew we had no chance at one of his guys, but Ruben and I sat down in his room and he opened one of his binders. We used what we found out to help us with some other players.”

Amaro recalled that he knew the Phillies had no chance to sign Boras' client shortly after the meeting started.

“I remember it,” Amaro said. “I think it was a pitcher. I knew we were in no position to sign him once the binder came out.”

It will be different this week in Las Vegas. The Phillies are flush with cash. Owner John Middleton wants to spend and contend right now, and Boras is likely to play to that sentiment.

Boras client Jake Arrieta signed a three-year deal worth $75 million with the Phillies in March. No free-agent received a higher average annual value last offseason, and afterward Boras gushed about the way the Phillies treated Arrieta.

In the middle of the season, Rhys Hoskins hired Boras as his client. Vince Velasquez and Nick Williams are also represented by Boras. Two decades have passed since that contentious battle between Boras and the Phillies over J.D. Drew and all the sore feelings are healed. Now the Phillies have to figure out a way to convince Bryce Harper that Philadelphia is the place where he’d like to spend the rest of his baseball life.

Wade offered one bit of caution.

“You always have to be prepared to do things on his timetable,” he said. “He does not subscribe to the idea that the best deal on the table that day is going to be the best deal.”