CLEARWATER, Fla. – John Middleton’s eyes lit up at the end of the one-hour interview inside his spring-training office at Spectrum Field. It was visible proof of how much he had enjoyed his lead role in remaking the Phillies, a task that started soon after the final pitch of the 2018 season and did not end until the managing partner sealed a $330 million deal with Bryce Harper shortly after making a cross-country flight to Las Vegas.

“I was a CEO when I was 25 years old,” Middleton said. “I was a year out of business school and it was a small company, but I was a CEO and I’ve been a CEO for almost 40 years now. I like being a CEO. I like the buck stopping on my desk.”

What Middleton did not like was the long, painful process of rebuilding a baseball team. It was already in progress when he became the club’s control person in November 2016 and when the Phillies regained some semblance of respect in 2018 by spending 39 days in first place before a late-season collapse, it was Middleton’s cue to accelerate the process.

The managing partner floored it.

Entering the offseason, Andy MacPhail knew exactly what he wanted.
ASSOCIATED PRESS
Entering the offseason, Andy MacPhail knew exactly what he wanted.

As usual, the team’s decision-makers – Middleton, president Andy MacPhail, and general manager Matt Klentak – met at the end of last season to discuss the needs for 2019. In order, MacPhail insisted that the Phillies needed to find a way to improve their team defense, cut down on their strikeouts and find a pitcher out of the bullpen who could handle the big left-handed bats that reside in so many National League East lineups. He thought the Phillies could use a left-handed starter, too.

Klentak mostly agreed with MacPhail, but warned that the price of a major overhaul would be costly in terms of free-agent dollars, top prospects and international pool money. He also warned that the roster building would not be complete at the end of the offseason and that payroll flexibility would be imperative to keep the team in contention for years to come.

“We need to recognize that the payroll is going to increase substantially,” Klentak told MacPhail and Middleton.

When it was Middleton’s turn to speak, he wanted to make one thing clear.

“Look,” he said, “I’m impatient. I want to do this now. I don’t want to do it incrementally over two offseasons or three offseasons. I know we’re inevitably going to have to do some things in July, but I want to push right now and do as much as we can.”

Another message along the same lines would come through the media in mid-November. Stick around long enough in professional sports and you’re bound to say something that goes viral. Eagles owner Jeffrey Lurie, for instance, will always be known for referencing his team as the gold standard long before he had a Super Bowl ring.

“That’s the bastardized version,” Middleton said.

John Middleton made a splash with his "stupid money" comment. It put pressure on Matt Klentak to produce.
YONG KIM / Staff Photographer
John Middleton made a splash with his "stupid money" comment. It put pressure on Matt Klentak to produce.

Middleton’s actual response to a question from a USA Today reporter about the Phillies’ offseason plans was this: “We’re going into this expecting to spend money. And maybe even be a little bit stupid about it. We just prefer not to be completely stupid.”

That quote made Klentak very popular this winter with player agents and his general manager peers. It also applied heavy pressure on the GM to get things done. For that, Middleton does not apologize.

“My statement was the verbal equivalent of Crossing the Rubicon,” Middleton said.

If you’re unfamiliar with that idiom, Middleton is more than happy to explain that Julius Caesar declared war in 49 B.C. by crossing the Rubicon River into Italy despite warnings not to from the head honchos in Rome.

“I wanted to send a signal to our players, our fans and to the organization that I was tired of the rebuild,” Middleton said. “It was painful to all of us and I wanted to put a goal out there. Let’s do as much as we can. Ideally, I wanted to do all of it. There are always times in this process, whether you are trading players or signing free agents, that the ask becomes very uncomfortable. The easy answer is to retreat.”

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The Phillies locked up their best pitcher with a four-year, $45-million contract extension.
YONG KIM / Staff Photographer
The Phillies locked up their best pitcher with a four-year, $45-million contract extension.

With the full support of Middleton and MacPhail, the Phillies went all in. The last move – signing Harper – will always be remembered first, but Klentak’s two other free-agent signings (left fielder Andrew McCutchen and reliever David Robertson) and two mega trades for shortstop Jean Segura and catcher J.T. Realmuto completed Middleton’s mandate.

“Matt was really playing three-dimensional chess,” Middleton said. “He was moving pieces around and he had multiple options every place we needed. He did a masterful job. He made so many good moves that it’s almost impossible to prioritize them one through six.”

Six?

“Yes, I include the Aaron Nola extension,” Middleton said. “That signing sent the message to J.T. Realmuto and Rhys Hoskins that we want to sign our young guys and keep them in our organization.”

The offseason ice breaker for Klentak was the deal for Segura and that may have been the most underrated transaction. The Phillies gave up shortstop J.P. Crawford and first baseman Carlos Santana for Segura, right-handed reliever Juan Nicasio and left-handed reliever James Pazos. Crawford did not make the Seattle opening-day roster and Santana was traded to Cleveland 10 days after moving to the Mariners.

Segura, 29, should be the Phillies’ most productive offensive shortstop since Jimmy Rollins’ departure and he is clearly an upgrade over Crawford and Scott Kingery, the two players who held down the position most of last season. He does have a reputation for being moody, but the Phillies feel as though he will be a good fit in their clubhouse.

Middleton loved the move.

The Phillies brass looked at the addition of Jean Segura as an improvement on offense and defense.
YONG KIM / Staff Photographer
The Phillies brass looked at the addition of Jean Segura as an improvement on offense and defense.

“It was a great move because it really solved three problems simultaneously,” the owner said. “It improved our defense at shortstop. It improved our offense at shortstop. And it opened up first base for Rhys Hoskins. Now, we could target outfielders and improve our defense in left field.”

That, in fact, was the next move. At the winter meetings in Las Vegas, the Phillies signed McCutchen, a veteran outfielder and former National League MVP, to a three-year deal worth $50 million. Middleton, who reads almost everything written about his team, heard complaints that it was too much money for too many years for a 32-year-old player trending down. The Phillies debated internally between McCutchen and Michael Brantley, a former Indians outfielder who signed for two years and $32 million with Houston. The Phillies decided they liked McCutchen’s durability more.

Middleton is sure it was the right decision.

“We were better off pushing through and signing him for what he signed for because he was critical to what we want to do,” Middleton said. “He brings not just a really good bat and improved defense in left field, he is an A-plus clubhouse presence who is going to make everyone better.”

Robertson, 34 next month, was added for two years and $23 million in early January and he checked off one of the boxes MacPhail had recognized as a 2018 weakness. Even though he is a right-hander, Robertson has held lefties to a career .188 batting average, which makes him the perfect late-inning reliever for manager Gabe Kapler.

The Phillies wanted to trade for J.T. Realmuto last season, but the deal stalled at the deadline. This winter, they made it happen -- but had to give up top pitching prospect Sixto Sanchez in the process.
YONG KIM / Staff Photographer
The Phillies wanted to trade for J.T. Realmuto last season, but the deal stalled at the deadline. This winter, they made it happen -- but had to give up top pitching prospect Sixto Sanchez in the process.

The trade for Realmuto might have excited Middleton and Klentak as much as the Harper signing energized the fan base. Talks with the Miami Marlins about Realmuto last July went nowhere and they were stuck there when Klentak tried again early in the offseason. And then the general manager picked up the phone in early February and tried again.

“I was finishing a workout when my phone rang,” Middleton said. “It’s Matt and he tells me he was on his couch thinking about how we could get even better.”

Realmuto was the answer, but the price – top prospect Sixto Sanchez, developing catcher Jorge Alfaro and underrated pitching prospect Will Stewart – was steep. Middleton wanted Klentak to keep his foot on the pedal.

“Anybody can criticize anything you do,” Middleton said. “This is a really good catcher. He hits and he hits for power and he can run the bases like few catchers can. He’s great behind the plate and another great clubhouse presence. Plus, he’s a former wrestler and he comes from a great wrestling family, so you know he has to be a stud.”

The inside joke there, of course, is that Middleton was a 158-pound college wrestler at Amherst and remains in love with the sport because of how it breeds toughness.

With Realmuto on board, one move remained for Middleton and his Phillies. It was the move that had been talked about since the day the free-agent market opened. It was going to be for either Manny Machado or Harper.

“We could have had a very good offseason without signing one of those two players,” Middleton said. “I don’t think anyone would have objectively disagreed with that statement. But to have a great offseason, we needed to sign one of those two players. That was imperative.”

Machado signed one week into spring training.

“Everybody wrote that we were anxious, we were nervous, we were behind the eight ball,” Middleton said. “I felt none of that. I was amused because I was reading a lot of stories about how I felt and they were being written by people I didn’t even know. I was always optimistic we’d sign one and I was always committed to signing one. That didn’t change when Manny signed. It simply meant that we redirected our efforts exclusively to Bryce.”

Manny Machado visited Citizens Bank Park in December. He chose to sign with the Padres just a week into spring training.
JOSE F. MORENO / Staff Photographer
Manny Machado visited Citizens Bank Park in December. He chose to sign with the Padres just a week into spring training.

It meant a flight from Clearwater to Las Vegas on Middleton’s private jet with the owner’s wife, Leigh, tagging along for support in the recruitment of Harper. It meant being prepared for anything and everything. Middleton went to Las Vegas and returned to Clearwater without a deal, leaving the door open for Harper to meet with the Los Angeles Dodgers and San Francisco Giants.

Middleton insisted he was not concerned.

“Flying back from the visit in February, I was personally committed to making that deal and emotionally committed to making that deal,” he said. “I knew the Dodgers and the Giants were coming, but in my mind he was already a Phillie. He had to go through those meetings, listen to what they had to say and listen to their offers, but there was no way we were not going to sign that guy.”

How could he be so sure?

“Just to be safe, we actually structured two deals in addition to the deal he signed,” Middleton said. “One was a short-term deal for three or four years with an AAV [average annual value] of $40 million in case he wanted to sign with L.A. Another was a six- or seven-year deal with a $35 million AAV in case he wanted to sign with the Giants. The idea was to checkmate him. We were going to offer the best deal no matter what.”

John Middleton got his man and now he finally has a roster that reminds him of some of the other great teams in Phillies history. You better believe he loved playing a part in putting it together.

“Five or six years ago, that comment about maybe being a little bit stupid, it would have meant nothing,” Middleton said. “I had no power, no authority. When I stood up and said it four months ago, it meant something because I’m the person in control and the managing partner. I don’t have unilateral authority, but I have a lot of authority. I’m fortunate that I have people like Andy and Matt and they are so good at what they do, so we always reach a consensus. But having the ability to lead this organization, I enjoy that.”

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