John Middleton probably wishes the Phillies were at a fork in the road because that would simplify the mess his team finds itself at this early stage of an offseason gridlocked by uncertainties. Instead, the Phillies managing partner is at a five-point intersection with a long to-do list that needs to begin with the hiring of the people best suited to make a lot of difficult baseball decisions.

Five years ago, when Middleton encountered this treacherous stretch of highway for the first time, he relied on newly hired president Andy MacPhail to bring in general manager Matt Klentak, a little-known 35-year-old assistant GM from the Los Angeles Angels. Klentak, with a surge of financial support from Middleton, was charged with bringing the Phillies into the analytical age, while MacPhail appeared to focus more on ballpark upgrades.

Citizens Bank Park, at sweet 16, remains a spiffy venue. But the Phillies' failure to post even one winning season during the MacPhail-Klentak era, combined with the COVID-19 outbreak, has placed Middleton in a precarious position. If the managing partner does not get things right this offseason, he could be looking at a serious dip in attendance even when the gates reopen to fans.

The Phillies need to become a winning team again if they hope to put people back in the seats even after the COVID-19 pandemic is over.
YONG KIM / Staff Photographer
The Phillies need to become a winning team again if they hope to put people back in the seats even after the COVID-19 pandemic is over.

In three of the five seasons since Middleton replaced David Montgomery as the point man for the franchise, the Phillies have drawn fewer than 2 million fans, something that had not happened since the move from Veterans Stadium.

Last season’s dip to the pandemic-driven figure of zero could not be avoided, but Middleton clearly needs to get the Phillies back to that golden era when 3 million fans consistently came through the turnstiles. Given the wobbly economic state of the country, that’s going to be difficult in the best of times and impossible without fielding a winning team.

Consider this: If the Forbes' estimate that the Phillies make $48 per fan is correct, that means the difference between drawing 2 million and 3 million fans is $48 million. That’s roughly the combined salaries of Bryce Harper and Zack Wheeler, the top two players on the payroll.

That’s why the first huge decision of the offseason needs to be made in the next few weeks and not after the New Year as Middleton suggested could happen a few weeks ago.

Barring some unforeseen circumstances, Theo Epstein, who officially became a free agent Tuesday when he resigned his position as the Chicago Cubs president of baseball operations, can be ruled out. In a letter to Cubs employees, Epstein said he plans to take the upcoming summer off and spend it with his family. At the young age of 46 and with his resume, he can afford to do that.

Besides, his demands figure to be sky high, and there is no shortage of other good candidates still available to take on the role as president of baseball operations and general manager.

The Athletic’s Ken Rosenthal and Jayson Stark, two of the most respected journalists in baseball, suggested that both the Phillies and New York Mets are reaching for the stars in their search for new baseball operations people, and that getting elite talent to come to their big cities could be a challenge.

Perhaps, but I think both big-market ballclubs are an attractive place for some of the game’s best talent. Michael Hill, the former president of baseball operations with the Miami Marlins, is a hot name right now, and an interesting one. He was the Marlins' GM when they drafted Christian Yelich and J.T. Realmuto in 2010 and when they signed Marcel Ozuna as an international free agent for $49,000 in 2008.

He’s also the guy who traded Realmuto for Sixto Sanchez and Jorge Alfaro. It would be interesting to see what he could do as a GM with a team that does not have to trade its greatest assets, a burden Epstein never encountered with the Cubs and Boston.

It’s already been written in this space that Kansas City director of player development and Cherry Hill native J.J. Picollo would make a fine general manager, and he remains available.

Picollo, 49, and New York Yankees special assistant Jim Hendry, 65, would make a nice younger-older combination as GM and president of baseball operations. The one thing Middleton should ask of his next president of baseball operations is that he be more involved with the baseball side of things. MacPhail, according to Phillies insiders, was way too hands off with Klentak.

A weakness of both MacPhail and Klentak was that they did not embrace the Phillies history. You can argue that it’s not a great history, which Middleton oddly did when he demoted Klentak. But since the advent of division play in 1969, the Phillies have had their share of success, winning 11 division titles, five NL pennants and two World Series. That should be celebrated and accentuated by the people in charge of the front office.

As a kid who grew up watching the Phillies, Picollo would certainly embrace the history. Hendry, meanwhile, has already had a working relationship with manager Joe Girardi. He was the Cubs' scouting director when Girardi returned to Chicago as a player in 2000. The two worked again together during Girardi’s time as manager of the Yankees after Hendry was hired as a special assistant to general manager Brian Cashman in 2012. Hendry is still in that role but would happily accept a promotion to president with the Phillies.

There are other good candidates, too. Brian Sabean, a three-time world champion in San Francisco, is among them. Middleton needs to make up his mind and get a baseball operations team in place because too many critical decisions lie ahead for his franchise.