Owner John Middleton on Phillies’ huge offer to Yoshinobu Yamamoto, saving the ‘powder’ for July, and more

CLEARWATER, Fla. — John Middleton’s private jet seats nine people. Seven were on board in December for a flight from Philadelphia to Los Angeles. The mission: to persuade prized pitcher Yoshinobu Yamamoto to be the first player from Japan’s Nippon Professional Baseball to sign with the Phillies.

“We pushed hard with Yamamoto,” Middleton said.

How hard? Team officials don’t disclose specifics of contract talks as a matter of course. But after meeting for three hours Dec. 14 with Yamamoto and his agents, and making a presentation that featured a video appearance by Bryce Harper, the Phillies offered more money than any team, according to multiple industry sources. That includes the Dodgers, who won the Yamamoto auction with a 12-year, $325 million bid that stands as the largest guarantee for any pitcher ever.

» READ MORE: The Phillies’ pursuit of Yoshinobu Yamamoto revealed their challenges in breaking through in Japan

The Phillies knew where they stood. They heard that Yamamoto wanted to play for the Dodgers or the Yankees. When the 25-year-old righty declined to visit Philadelphia as part of a trip to meet with the Yankees in New York on Dec. 17, one day after dining with Mets owner Steve Cohen at his home in Connecticut, the Phillies understood they weren’t on his radar — except perhaps to bring up the Dodgers’ offer.

“If I had to do it all over again, I’d still do what we did because I think you have to be able to look yourself in the mirror and say, ‘You know what? I tried,’ ” Middleton said from his third-floor office at BayCare Ballpark in a wide-ranging, 40-minute interview with The Inquirer. “It’s kind of easy in that situation to say, ‘We’ll just stay home and not even make an effort, or we’ll make a token effort because we’re probably going to wind up losing him.’ I’m not built that way. If he’s really good, you make the effort because you never know when you’ll change somebody’s mind.”

Other free agents turned down Middleton’s moola this winter for various reasons. Jordan Hicks wanted a chance to start with the Giants after years of pitching in relief. Reliever Robert Stephenson, also a hard-throwing righty, signed with the Angels to be close to his home in Southern California.

“We were going to sign Yamamoto for a lot, a lot of money, and we never thought twice about it in terms of a budget impact. We thought about it in terms of a competitive impact,” Middleton said. “Same thing with Hicks and Stephenson. We thought they were just really good players that were going to help move the needle.”

So, the Phillies are running it back with the team that got staggered by a Diamondbacks punch in Game 6 of the NL Championship Series and knocked out in Game 7. Both losses came at home. Neither was easy to digest for the Phillies’ billionaire owner, who was at Yankee Stadium for Game 6 of the 2009 World Series and Citizens Bank Park when Ryan Howard collapsed on the turf while making the final out of the 2011 division series.

“If you’re using the phrase, ‘Get over it,’ it’ll never happen,” Middleton said. “I mean, ‘09, ‘10, and ‘11 still hurt. You don’t get second chances to win that year. To be up 2-0 [in the series] and heading to a place [Arizona] where you took three out of four in August and lose two out of three, and then lose two at home, when you have your foot on your enemy’s throat, you kill ‘em. And we didn’t do it.

“I’m angry. It’s a funny word to use, but when you lose like that, I get angry. And frankly, if people don’t get at least a little angry, I’m not sure you care enough.”

» READ MORE: Bryce Harper has a revised Phillies contract on his mind. John Middleton doesn’t want him to think about it.

Lately, Middleton’s emotional investment is surpassed only by his financial one.

In 2020 and 2021, he walked the payroll to the luxury-tax threshold but didn’t cross it. He insisted he would pay the tax if the team was a player or two away from the World Series. But after the pandemic-shortened 2020 season — and ensuing layoffs of 80 club employees — it was fair to wonder if he regarded the luxury tax more like a salary cap.

That perception is long gone. Middleton floored it through the luxury-tax stoplight in the spring of 2022 with the twin signings of Kyle Schwarber and Nick Castellanos, then pushed harder on the pedal after the Phillies’ rousing run to Game 6 of the World Series by throwing $300 million at Trea Turner. The payroll came in at $244,413,284 in 2022 and rose to $255,327,012 last year, with the Phillies paying annual tax bills of $2,882,657 and $6,977,345, respectively.

The Phillies are projected to surpass $260 million this year, which would put them over the second-tier threshold and boost their tax rate to 62%. Only the Mets, Yankees, Dodgers, and possibly Braves will have a higher payroll.

Did Middleton ever envision opening the checkbook this much?

“One of the things I always said is I intend to win, and I intend to push the envelope to win,” he said. “There’s different ways you can push the envelope, and spending is just one of those ways. I’ve never thought about it quite the way you phrased the question. I’ve never thought about it as breaking the luxury tax. It’s always been about, is this player a difference-maker?”

It’s a label that Middleton said he hears often from president of baseball operations Dave Dombrowski. Various reports throughout the offseason connected the Phillies with big-ticket free agents. A case could be made that they would upgrade their starting rotation by adding, say, unsigned lefty Jordan Montgomery, who starred in the postseason for the Rangers.

» READ MORE: Here’s why Matt Strahm expects new Phillies utilityman Whit Merrifield to ‘be a good fit here’

But after watching their top three pitching targets sign elsewhere, Middleton said Dombrowski advised holstering the wallet for now.

“What Dave decided we’d do — and I agree with him — is save the powder,” Middleton said. “He said, ‘If you don’t spend it now, you could always spend it in July and maybe make a better, more aggressive trade, and you’ve got the money to pay for it.’”

Besides, Middleton doesn’t mind running it back with a roster that played to a 100-win pace after June 2 last season.

“I would almost argue that running it back is a good idea,” he said. “Some of the young guys are going to be better with an extra year, whether young pitchers like [Cristopher] Sánchez and [Ranger] Suárez, or you’ve got [Alec] Bohm and [Bryson] Stott, you’ve got [Brandon] Marsh and [Johan] Rojas. If you’ve got some people at the other end of their career, they may be sliding a little bit, but we don’t have anybody at that 36, 37 age yet.

“You didn’t see a lot of change in the 1980 team or the 2008 team. The core of those teams really stayed the same for the two respective runs.”

But players from the 1980 team, in particular, believed that their run had an expiration date. After the Phillies lost in the NLCS in 1976, 1977, and 1978, and missed the playoffs in 1979, Larry Bowa often recalls then-owner Ruly Carpenter vowing there would be changes if they fell short again in 1980.

Middleton said he’s “not even close to that” with this cast of characters.

“And I don’t think Dave is, either,” he said. “It’s not even in the thought process.”

If anything, Middleton and Dombrowski want to keep the roster together longer. Talks are underway with ace Zack Wheeler on a $30-plus-million-per-year extension, with Middleton wishfully predicting “we’ll make it work.” Harper and Turner are under contract through 2031 and 2033, respectively, and Nola through 2030. None of the everyday players is older than 33 (J.T. Realmuto on March 10).

» READ MORE: Trea Turner gets right to work rebounding from ‘brutal’ defensive showing in Year 1 with Phillies

The Phillies drew more than 3 million fans to Citizens Bank Park last season for the first time since 2013. Middleton takes it as an indication that they paying customers are fond of a roster they’ve gotten to know well.

“I think the players we’ve added through free agency have the right personalities for Philadelphia. And that’s not by accident,” Middleton said. “Everybody understands that Philadelphia is a strong market, and you need to be a strong-[minded] player to play here. We’ve looked for the character beyond the athletic ability. And [fans] have reacted, I think, really genuinely and warmly to those players.”

Imagine how a World Series title might go over. Until then, there’s only the sting of Game 7.

“I always use that kind of experience and emotion — the anger part — to fuel me,” Middleton said. “It’s what propels me in the future. The good news is, I’m sensing our guys have focused on the same way.”