“I think a lot of those guys over there in the front office are second-guessing themselves. I mean, I would, too.” — Atlanta Braves left-hander Dallas Keuchel

Yeah, Dallas Keuchel went there.

At the risk of sounding inelegant after spinning six stellar innings Wednesday night at Citizens Bank Park, the veteran lefty answered a question about whether he derived extra satisfaction from dominating a team that had passed on signing him as a free agent by confirming that the Phillies never really showed interest.

Then, he rubbed their nose in it.

Here’s the thing: Keuchel is right.

When the season finally ends, regardless of whether the Phillies miss the playoffs for an eighth consecutive year or rally to get in as the National League’s second wild card, general manager Matt Klentak should have regrets. A lot of regrets. More than just not signing Keuchel in the offseason or before the Atlanta Braves snagged him for one year and $13 million in early June.

If the Phillies fall short of the postseason, they will surely blame a wicked spate of season-ending injuries, which claimed left fielder Andrew McCutchen in June and No. 2 starter Jake Arrieta in August and wiped out almost the entire bullpen (David Robertson, Seranthony Dominguez, Tommy Hunter, Pat Neshek, Adam Morgan, and Victor Arano).

But the real reason for their absence from October will be the shortcomings of their pitching staff — specifically the starting rotation — and there really isn’t any way around that.

Keuchel might be the embodiment of the Phillies’ failure to improve the rotation, but there were other opportunities, too, long before the July 31 trade deadline, when Klentak and team president Andy MacPhail didn’t see the sense in going all-in on a move for a pitcher when the likeliest reward would have been a chance to play in one wild-card game for the right to face the NL-best Los Angeles Dodgers in a best-of-five division series.

In spring training, Klentak extolled the Phillies for having “an objectively excellent offseason.” He even got a three-year contract extension from owner John Middleton.

But he made a costly gaffe by misjudging the upside of Zach Eflin, Vince Velasquez, and especially Nick Pivetta. Never mind that all three starters faltered badly down the stretch last season or that the development of young pitchers rarely follows a straight line.

Maybe Klentak will judge himself more harshly in his end-of-year assessment.

Keuchel kindly offered one second-guess of Klentak. Here are two others that almost certainly would have been difference-making moves for the Phillies.

Tampa Bay Rays right-hander Charlie Morton might have been the steal of the offseason free-agent pitching market.
ALLIE GOULDING / MCT
Tampa Bay Rays right-hander Charlie Morton might have been the steal of the offseason free-agent pitching market.

Not signing Charlie Morton

OK, so Klentak had been down this road before.

In one of his first moves as a general manager, in December 2015, he acquired Morton from the Pittsburgh Pirates for minor-league pitcher David Whitehead. Talk about a steal, right? Well, it might have been if only Morton hadn’t blown out his hamstring after four starts and missed the rest of the 2016 season.

Two seasons later, Morton hit the free-agent market with the force of a mid-90s fastball. Having revived his career with the Houston Astros by spinning a better curveball and picking up velocity on his heater, Morton won a World Series ring in 2017 and became an All-Star in 2018. At age 35, the right-hander had come to define "late bloomer."

Morton was open to returning to Philadelphia, too. Looking back on his ill-fated 2016 season, he believed the seeds for his successful second act as a major-league starter were sewn during that spring training. He also had the endorsements of former Phillies manager Pete Mackanin and several others in the organization, who suggested that Morton would be a good fit, according to multiple sources.

“I really liked being in Philly,” Morton said at the All-Star Game in 2018. “I liked being with that group, those younger guys. Unfortunately, it didn’t work out.

"But I felt like there was something there with the way the ball was coming out of my hand. I came to spring training and felt like my arm was just moving so easily. I looked up to see how hard I was throwing. I was throwing hard. My stuff was moving. I was really excited about that year.”

But after refusing to commit a sixth year to top target Patrick Corbin and getting outbid by the New York Yankees for fellow lefty J.A. Happ, the Phillies decided none of the other free-agent pitchers represented an upgrade over Eflin, Velasquez, and Pivetta.

Morton’s performance this season indicates otherwise. In 176⅓ innings with the Tampa Bay Rays, he has a 3.11 ERA and 11.1 strikeouts per nine innings, better numbers than even last year with the Astros — and all for the relative bargain of a two-year, $30 million contract.

Cincinnati Reds right-hander Sonny Gray has had a bounce-back season after being traded by the New York Yankees in January.
John Minchillo / AP
Cincinnati Reds right-hander Sonny Gray has had a bounce-back season after being traded by the New York Yankees in January.

Not trading for Sonny Gray

Unimpressed by the free-agent options beyond Corbin and Happ, the Phillies looked into several potential trades for starting pitching. But it takes something to get something, and the asking prices were predictably high.

Take, for instance, the Seattle Mariners’ talks about James Paxton. For a 30-year-old lefty with two years of control, they were seeking multiple top-10 prospects, including a touted pitcher. In the Phillies’ case, that likely would have meant Sixto Sanchez, the 21-year-old right-hander who was packaged later in the offseason for catcher J.T. Realmuto. Seattle eventually sent Paxton to the Yankees in a deal that brought back young lefty Justus Sheffield.

The Phillies weren’t especially high on Arizona lefty Robbie Ray. They did have discussions about Texas lefty Mike Minor but couldn’t match up on a deal. Want proof that the pitching market favored the sellers? Consider that neither Ray nor Minor (nor Detroit lefty Matthew Boyd, for that matter) was traded last winter or before the July 31 deadline.

But then there was Sonny Gray. Yankees GM Brian Cashman told the world early in the offseason that he intended to trade Gray, seemingly diminishing the 29-year-old right-hander’s trade value even more than a lousy 2018 season or the fact that everyone could see he wasn’t a fit for New York.

Some within the Phillies organization believed Gray’s numbers away from Yankee Stadium (3.17 ERA in 2018) made him a strong bounce-back candidate. But rather than striking a deal, they watched as the Yankees sent Gray to the Reds for Shed Long, an infielder ranked by Baseball America as Cincinnati’s seventh-best prospect.

The Phillies’ assessment of Gray proved correct. Reunited with Reds pitching coach Derek Johnson, his coach at Vanderbilt, Gray has a 2.80 ERA and 10.4 strikeouts per nine innings in 29 starts.

Another Klentak regret? It should be.