Phillies: 5 lessons to learn from 2019 World Series

CLEARWATER, FL - MARCH 02: Phillies Managing Partner John Middleton shakes hands with Bryce Harper as Vice President & General Manager Matt Klentak in middle looks on during the press conference to introduce Bryce Harper to the media and the fans of the Philadelphia Phillies on March 02, 2019 at the Spectrum Field in Clearwater, Florida. (Photo by Cliff Welch/Icon Sportswire via Getty Images) /

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26 July 2014: Philadelphia Phillies starting pitcher Cliff Lee (33) winds up to pitch during a Major League Baseball game between the Philadelphia Phillies and the Arizona Diamondbacks at Citizens Bank Park in Philadelphia, PA. (Photo by Gavin Baker/Icon SMI/Corbis/Icon Sportswire via Getty Images) /

2. Don’t be careless

It’s one thing to make a bet on a 30-year-old because you think he will provide value for your team. But it’s another thing to do it just for the sake of “being aggressive”. The Phillies have shown a desire to add players through multiple outlets, including free-agency and trades, and they should use both avenues to mitigate the risk of pouring hundreds of millions more dollars into long-term deals for free-agents.

The team already has two 30-plus players: Andrew McCutchen and Jake Arrieta, and both are coming off injuries. We have no idea what this season has in store for them. Adding a free agent starting pitcher could very likely add another “high-risk” pitcher to the roster.

In the early portion of the 2010s when the Phillies were contending in a five-year run, then-GM Ruben Amaro, Jr. pushed all the chips to the table, trading for Roy Halladay and Roy Oswalt, and followed those moves by signing Cliff Lee, entering his age-32 season, to a five year deal and a sixth-year vesting option or buyout that eventually cost the Phillies a total of $120 million. Lee pitched well in the first three years of the deal (only one of which the team made the postseason: 2011), started 13 games in the fourth year, and didn’t pitch again in the majors.

The Phillies ended up paying Lee almost $45 million for baseball that he never played.

While that’s the risk that you take when you invest in an aging player, it’s a risk that’s worth taking if you feel your team is right on the cusp of winning it all.

The catch? I’m not sure the Phillies are there yet – they have some more work to do before I think it’s worth taking on too much extra risk. But I don’t think they should miss out entirely on the elite talent available to them this offseason.