Does John Middleton regret the J.T. Realmuto-Sixto Sánchez deal?

While Philadelphia Phillies managing partner John Middleton did say that the team hopes to retain two-time All-Star catcher J.T. Realmuto, he acknowledged that a trip to free agency is all-but-certain. Middleton suggested that external factors, including projected 2021 revenues, may determine whether the Phillies are able to retain Realmuto.

Meanwhile, Sixto Sánchez, the marquee piece the Phillies traded to the Miami Marlins for Realmuto in February of 2019, earned a playoff series-clinching victory Thursday. Counting his postseason win over the Chicago Cubs, Sánchez has a 3.07 ERA through his first eight major league starts. Hall of Famer Pedro Martinez has referred to the 22-year-old righty as “a mini-me with better stuff.”

So with Realmuto potentially one offer away from leaving in free agency, does Middleton look back on the deal that sent a potential ace away to a division-rival with some regret?

“That’s an interesting question, because the fact of the matter is at the time it was being considered, my position was I’d be willing to trade Sixto, as long as you extend J.T.,” Middleton said Saturday evening. “And if you don’t extend J.T., I wouldn’t trade Sixto because we weren’t at the point in the development of the team where the benefits we were getting matched what we were giving up.”

Middleton went on to compare and contrast acquiring Realmuto with the 2009 trade that landed the team Cliff Lee from the Cleveland Indians. Both deals allowed the Phillies to acquire superstar talents, but the Phillies were at entirely different places in their organization when they were made.

In July of 2009, the Phillies sent a package headlined by Carlos Carrasco to the Indians for Lee, knowing that Lee could become a free agent after the 2010 season and Carrasco had a high ceiling. However, at that time, they were the defending World Series Champions, and acquiring Lee set them up to win a second consecutive National League pennant.

When the Phillies trade for Realmuto ahead of the 2019 season, they were coming off of six consecutive losing seasons. They had already traded for Jean Segura and signed Andrew McCutchen, with the hope that they would still sign one of Bryce Harper or Manny Machado. But Middleton admitted that the Phillies probably pushed their chips to the center of the table sooner than they were ready to.

“…At that point when we traded for J.T., we weren’t the defending World Series Champions, we were trying to get back to the playoffs,” Middleton continued. “The point I made was we need J.T. now, but we really need J.T. in three, four, five, six years from now. And if all we get for him is two years, that’s not the same as two years of Cliff Lee in 2009. And so, that was my position. He’s a great player, but we gave up a great player. To me, we just needed to hold fast and be firm on not giving up Sixto for just two years at that moment in our time. We were a little early in the development to make that kind of a play.”

Given the affinity Harper showed towards Realmuto during his time with the Washington Nationals – and since the two have been teammates in Philadelphia – there’s long been a thought that the Phillies may have felt they needed to trade for him to assure Harper signed. Was that the case?

“No,” Middleton responded. “I’m sure it helped, but no.”

So if the Phillies didn’t feel pressure to acquire Realmuto to get Harper to sign on the dotted line, why, against Middleton’s intuition, did a trade get completed without a long-term deal?

“Because the baseball people thought they could get the extension,” Middleton said bluntly.

“One of the problems I have – and I think most owners have – is we’re not baseball people. We’re not scouts for three or four years, we don’t then go into the farm system for three or four years…because that’s the way you really learn a business. That’s the way I learned the businesses that I ran. I started working in our factory when I was 16 years old. I was a salesman for a period of time. That’s how you have to learn.

“So there’s always been a bit of diffidence, because you look at these decisions and you’re talking about making evaluations on things that you really don’t have grounding in. How do I evaluate a player? What’s my basis to say that this player is going to develop well or not develop well? And so you tend to – and I did this – listen to the “baseball people.” You let them guide you because that’s what you pay them for.”

As it turns out, though, the Realmuto trade may have served as a turning point for Middleton. It’s why he stepped in and fired Gabe Kapler last offseason against his front office’s wishes, and may color future baseball operations decisions within the organization.

“But that experience, is exactly why a year ago when we were all sitting around in the press conference room talking about Gabe [Kapler] and why I was stepping in to make this decision, it was because I just decided ‘You know what? If I feel strongly about something that I feel is important, I’m not going to let it slide again. I’m not going just defer to other people.’ You live and you learn. That experience on that trade – you have to learn from what you do in the past – and that has shaped me going forward.”

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