Phillies must weigh Jake Arrieta and Lance Lynn against lessons from past | David Murphy

The most compelling argument for throwing caution to the wind is one based on hindsight.

The Phillies’ last window of dominance imparted plenty of lessons with the way that it ended, most of which involved the precipitous nature of the backside of the aging curve and the consequences that await an organization that underestimates the level of risk present in its portfolio of talent. These were important lessons, and all indications are that ownership has learned them, as evidenced by the fact that Jake Arrieta and Lance Lynn are still free agents and not Phillies.

Yet as Matt Klentak and Andy MacPhail sit on the outskirts of a pitching market desperate for an infusion of impulsively spent dollars, it’s worth considering another regret from the last golden era, this one focusing on the front end of things, and the windward side of that aforementioned aging curve.

Four of the saddest words in life are what might have been. Regarding the Phillies’ dominant run from 2008-11, our focus tends to rest on the tail end of things: Chase Utley’s knees, Ryan Howard’s Achilles, Roy Halladay’s entire body. No doubt it was an era of missed opportunities, but to fixate on the waning years is to miss the true misfortune: that the end arrived so soon after the start.

Such a thing can happen one of two ways: a premature finish, or a delayed beginning. Knowing what we know now about the manner in which a drug-tested population ages, it seems evident that the Phillies’ greatest miscalculation wasn’t the assets they acquired, but the time at which they did so.

Remember that spring when Chase Utley’s knees first emerged as a problem? It was 2011, and he was 32 years old. At the time, it seemed like fate was cutting down our youth. The previous season, 21 players age 32 or older logged 500 plate appearances of above-league-average production. In each of the two seasons before that, 27 such players had done so. Last year, that number was 15.

Howard’s ruptured Achilles came in the final plate appearance of his 31-year-old season. Halladay finished second in the Cy Young voting at age 34. At the time, these developments might have felt like uncharacteristic misfortunes of a snake-bitten team. Now, given what we know, they look like the fairly typical decay of a roster in its late prime.

Turns out, when the Phillies won the World Series in 2008, their window was already closing. It was the last season that Jimmy Rollins’ OPS cracked .750. Between 2004-08, he hit .286/.342/.468 and averaged 18 home runs. Between 2009-11, he hit .255/.316/.403 with an average of 15 homers.

Like Rollins, Howard’s peak came between the ages 25-29, when he hit .279/.376/.586 with 44 homers per season from 2005-09. Utley’s came between the ages of 26-30, also 2005-09: .301/.388/.535 with an average of 29 homers.

The reality of the greatest era of baseball in Phillies history is that it should have begun four years earlier than it did. From 2004-07, their lineup finished in the top three in the National League in runs scored. Imagine if they could have combined it with an injection of pitching as the one they delivered starting in 2009.

Imagine. It’s a question the Phillies will attempt to avoid this time around, and we should not understate the complexities of doing so. This year’s team is not quite where the last generation was back in 2005, when Pat Burrell and Bobby Abreu were already established as legitimate top-half-of-the-order hitters. There is a highly conceivable world in which J.P. Crawford and Maikel Franco and Jorge Alfaro all struggle, and that world might be an unsalvageable place with or without Arrieta or Lynn or even both in the rotation.

Every dollar the Phillies commit this offseason is one less dollar they can spend on future talent that, in theory, will be closer to the good side of the aging curve than whatever talent they sign now will be at that time. Each year of a deal comes with more and more risk. The further into a contract they get before their lineup is producing at a playoff-caliber level, the more risk they have needlessly assumed.

The pitching market is fraught with risk even on the front end of deals. From 2012-15, Jordan Zimmermann averaged 203 innings with a 3.13 ERA for the Washington Nationals. Since signing a five-year, $110 million deal with the Tigers in 2016, he has averaged 133 innings and a 5.60 ERA. If that were Arrieta this year, it would mean the Phillies enter next offseason where they are now, with 21 million fewer dollars to spend.

Which brings us back to the lessons we referenced at the top. That the current rebuilding process was necessitated first and foremost by an inadequate appraisal of depreciation is beyond dispute, and there is a strong argument to make that, in their present moment, the potential benefit the Phillies could realize from a big-ticket starter in 2018 is outweighed by the potential detriment his contract could inflict on their ability to contend in future seasons.

But, then, there is that argument’s inverse. Rhys Hoskins, like Howard in 2005, will be 25. Odubel Herrera, like Rollins, will be 26. Nick Williams, like Utley at his age (24), has yet to break out. The unfortunate truth about opportunity is that it reveals its arrival only after it is gone.