For a while, it looked like they might have a shot.

The Phillies caught fire to start the 2018 season, surging to 31-23 at the end of May, to a 2 1/2-game NL East lead in late July, and to a season-best 15 games above .500 on August 7. They collapsed after that, a would-be worst-to-first Cinderella story turning into some ugly truths about the multiple roster holes that still plagued the team.

The Phillies opened last season with the ninth-lowest payroll in baseball, trailing such traditional spending juggernauts as the Royals and Reds. Multiple young, inexpensive players responded with big numbers early in the year, only to turn into pumpkins by year's end. Now, the Phillies plan to spend big money to plug some of those roster holes.

They can easily afford it. The Phils inked a new TV deal four years ago that not only pays out a total of $2.5 billion in rights fees; it also comes with a 25 percent ownership stake in Comcast SportsNet Philadelphia that could be worth billions more.

  • 2018 Result: 80-82, third place in NL East
  • Key free agents: None
  • Needs: Shortstop, third base, outfield, starting pitching, relief pitching

No team has been more frequently linked to this winter's marquee free agents than the Phillies. Manny Machado and Bryce Harper are the best players available this winter; they're two of the most desirable free agents in baseball history given their combination of mid-20s youth, skill, and potentially untapped upside; and they would also fill arguably the two biggest positional holes on the roster. Given how weak shortstop, third base, and right field were last season, you could project a potential five-win upgrade if the Phillies were to sign either free-agent superstar.

Even if they do splash $400 million on either player, that might not be enough to shove the Phillies over the top in the NL East. World Series contenders need more than a big-ticket free agent to make a deep October run. Young talent needs to emerge, such that a Harper or Machado becomes the final piece of the puzzle, rather than merely a player who shoves the Phillies over .500, into the fringes of a wild-card race.

Consider the past three World Series winners. The Cubs snapped their 108-year drought by first building a dynamic young core led by Kris Bryant, Anthony Rizzo, and others. Only afterwards did they throw big money at Jon Lester and Jason Heyward to go for it all. The next season, the Astros rode homegrown stars Jose Altuve, Carlos Correa, and George Springer, supplemented them with A+ pickup Justin Verlander, and won their first Fall Classic in franchise history. The 2017 Red Sox were already a good club, buoyed by Mookie Betts, Xander Bogaerts, Andrew Benintendi, Jackie Bradley, and others; $110 million pickup J.D. Martinez proved to be the final piece of the puzzle.

Do the Phillies have that kind of player infrastructure in place for a Harper or Machado to push them over the top? That's a tough one to answer.

We now know that Aaron Nola is a true ace, his 2018 breakout season set to earn him a top-three Cy Young finish. Young slugger Rhys Hoskins's sophomore season wasn't quite as impressive as his rookie debut, but he still slammed 34 home runs. After that, we've got a murderers' row of question marks.

Center fielder Odubel Herrera's combination of youth, skill, and cheap contract made him one of the most desirable commodities in all of baseball. But it's tough to know what to make of him now, coming off an abysmal .214/.279/.342 second half. Second baseman Cesar Hernandez was never regarded in the same category as Herrera, but a brutal second half of his own negated a strong start to 2018 (and potential breakout season). Should we evaluate mid-20s right-handers Nick Pivetta, Vince Velasquez, and Zach Eflin based on their robust strikeout rates and other strong peripherals that made them better-than-average pitchers in 2018 based on fielding-independent numbers? Or were their ERAs in the mid- to high-4.00s more indicative of their abilities? And what are we to make of J.P. Crawford and Scott Kingery, two once highly-touted prospects who've struggled mightily early in their major-league careers?

To answer these questions, the Phillies might want to do something even bolder than merely sign a superstar: They might want to keep going even after a potential Machado or Harper signing. As much as analytically-oriented rookie manager Gabe Kapler might've enjoyed making fantasy baseball players crazy with his unpredictable bullpen usage, it's tough to look clever when your pen ranks a lowly 23rd in park-adjusted ERA. That could prompt Philly to shop for more relief help, after handing multi-year deals to Tommy Hunter and Pat Neshek last year. A veteran lefty like J.A. Happ could make lots of sense as a way to break up the team's armada of young (and still mostly unpredictable) right-handed starters. Hell, if the Phils want to bag a pitcher who could help the rotation and the pen, maybe they could get a hometown discount on hard-throwing, curveball-launching veteran Charlie Morton, who cited his desire to be close to his wife's family's Delaware home ahead of free agency.

With that seductive early-2018 success fresh on their minds, a giant war chest to play with, and tons of needs, the Phillies could be major buyers this winter. But the path to Hot Stove gold could also be tricky to navigate. With mega-market teams like the Yankees, Dodgers, and Giants carefully ducking under the luxury-tax threshold last season, the spending math starts to make a lot more sense for those teams to go back to their spendthrift ways. If that happens, the Harpers, Machados, and even the Mortons could tougher to land than the Philly Phaithful might expect.

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