SCOTTSDALE, Ariz. — Scott Boras arrived last March in Clearwater, Fla., to put the finishing touches for the second-straight year on another free-agent contract. He sat on top of the Phillies dugout as Bryce Harper buttoned his pinstripe jersey. A year earlier, baseball’s super agent watched Jake Arrieta tug on a red cap.

The Phillies, as they began to expand their payroll in recent seasons, formed a relationship with Boras, the agent to many of baseball’s brightest stars. Boras admires John Middleton’s willingness to win by spending, especially during an era he described the majority of the league to be in “competitive hibernation.”

Soon, that relationship could add another layer. The Phillies are desperate for starting pitching and Boras represents Gerrit Cole and Stephen Strasburg, the top free-agent starters. The Phillies laid a foundation this week at the General Managers Meetings to improve their starting rotation, which is their No. 1 priority this offseason.

And there could be a way that Boras finds himself at a Phillies news conference for the third-straight offseason.

The Phillies, according to a source, will make a heavy push for Cole, who was dominant in the postseason for Houston and finished second on Wednesday night for the American League Cy Young Award. But Cole grew up in Southern California and played at UCLA, which led to numerous rumblings that he would prefer to sign this winter with a West Coast team like the Angels or Dodgers. So how much does geography matter for Cole?

“I don’t think geography matters to any of these guys as much as the continuance of winning and being able to achieve their goal of getting that rare ring,” Boras said. “And I think in Gerrit’s case, when you’re that close, you’re looking at this process as one where I’ve got a box to check and I want to go out and put together the best effort to put me in that position to do that.”

Cole’s contract, which could near $300 million, will likely be the most lucrative deal signed by a free-agent starting pitcher. Just like Harper’s deal did for position players, Cole’s contract will increase the asking price for future pitchers and provide a benchmark to clear.

That is why it is extremely unlikely that Cole will settle on lesser deal just to play closer to home. The highest bid, as it almost always does, will win. And the Phillies have the ability — and the owner — to be the highest bidder.

“I don’t see any stop sign in John’s pursuit of his goal and that’s a world championship,” Boras said of Middleton. “He’s an owner that has been very straightforward about his path and his commitment. He’s very, very involved in the franchise and it’s really good to see owners really be that committed to their city, to their team. We should really have a dynamic where when people are that involved I think they’re going to be as competitive as they feel they need to be to create the winning product they want.”

Boras said he met over the last few days with numerous teams about his two pitchers, who the agent said are creating a more expansive market than Harper did. The pursuit for Cole could be a tight race as the Phillies will likely have to outbid both hometown L.A. teams along the likes of the Yankees, Padres, and Astros.

“If this were major-league Christmas, we would be looking at 30 stockings that clearly wanted a lump of Cole,” Boras said. “I think starting pitching has become back in vogue. It’s an aggressive market.”

Phillies general manager Matt Klentak said this week that “the rotation is definitely and area that we are going to look into this winter.” The Phillies, Klentak said Wednesday, currently see their rotation as Aaron Nola, Jake Arrieta, Vince Velasquez, Zach Eflin, and Nick Pivetta. But that was the same group that faltered last season.

Changes are coming. The Phillies will look this winter to add two starters, knowing that prospect Spencer Howard is charging toward the majors and could be seen as a third addition. First, they need to find a difference maker. They will start at the top, hoping to land either Cole or Strasburg. Boras expects both pitchers to sign quicker than Harper and Arrieta, who both joined the Phillies less than a month before the season started. If so, Boras would not have to go to Clearwater this year to complete the deal.

“There are general managers who I said four or five years ago to that ‘You’re going to have a very hard time winning a world championship if you don’t sign this player.’ And I’m very happy to say that player was Max Scherzer,” Boras said. “I told that to three teams and they have not won and he did win. The reality of it is that those No. 1 kind of guys, those special arms, take you through the playoff seas.

“You have to have them because when it comes down to that, you end up throwing 70-percent of the innings among three guys. I think they understand the nature of the game. Again, it all boils down to what’s important to them. What’s important to their ownership. What drive do they have to where they are really going to take risks. All of these things are risks in their minds. None of them are comfortable with it. They never are. But that’s how you win. You take risks. You pay Max Scherzer $30 million a year when no one else would and by doing that, you’ve been rewarded.”