A Unified Theory of Contention Windows and Free Agent Pitching

Few teams have sounded the alarm indicating their move from rebuild to contention like the Cubs did in the winter of 2014. Coming off of a 73-win, last-place season, the Cubs made aggressive plans for the offseason, and they executed like the virtuosos they were: on November 4, Theo Epstein and Jed Hoyer nabbed Joe Maddon away from the Tampa Bay Rays, and one month later, at the Winter Meetings, the pair inked former Red Sox ace Jon Lester to a six-year, $155 million deal. Lester’s contract was, at that point, the largest in franchise history, besting Alfonso Soriano’s eight-year, $136 million deal signed in 2006, and he immediately slotted in at the top of an impressive rotation already featuring the emergent pair of Jake Arrieta and Kyle Hendricks.

We know how well Lester has worked out. In 2015, the Cubs won 97 games, as Lester put up five WARP on the back of a stellar 3.01 DRA. The lefty wore a pair of tough losses in the NLDS and NLCS that October, but in 2016 Lester came back just as strong and all but replicated his great 2015. This time, he snagged a second-place Cy Young finish, the NLCS co-MVP, and a World Series ring. I think that the Cubs organization, and just about every single Cubs fan, is pleased with Lester, despite a lackluster 2017 and the prospect of diminishing productivity over the next three seasons as he ages into his late-30s. After all, he was a cog in the first World Series championship for the club in 108 years, and his tenacity, intensity, and craft made for exciting pitching.

Now, as Lester enters the back half of his six-year deal, the Cubs rotation is in flux. Jake Arrieta is departing via free agency and is unlikely to return; José Quintana has assumed the reigns of de facto staff ace after moving a few miles north on the Red Line last summer; John Lackey is gone, perhaps retired; Tyler Chatwood is the shiny new toy that Cubs coaches have to tinker with this spring; and Kyle Hendricks—well, Hendricks is still Quintana’s co-ace, quietly posting some of the best numbers of any pitcher since 2015. Where does Lester slot into this equation? And, more importantly (and relatedly), will the Cubs really roll with Mike Montgomery as the fifth starter, or will they finally take their finger out of the dike and let the flood waters that are Arrieta and Yu Darvish and Alex Cobb wash over them?

At this point, advocating for a club to sign a starting pitcher, or any free agent, is a quixotic exercise, so I’m not going to sit here and bang the drum for Darvish as I’ve done this whole offseason. We know why this free agent market has been historically slow. But there are those who are content to stand pat with the Cubs’ rotation regardless of salary suppression and the war on free agency, regardless of Chatwood’s unknowability and Montgomery’s mediocrity and Lester’s age. I think that it’s time to discuss free agent pitchers, the Cubs’ contention window, and a generalizable strategy or framework that we can apply to teams in the Cubs’ position.

To do this, I want to first return to Lester’s signing. The club was coming off of a 2014 season in which they spent a mere $99 million on player salaries, so they were clearly positioned to spend a lot of money going into 2015 when they expected to contend. It was a savvy, if obvious move to bring in the veteran lefty. For the next three seasons, the Cubs forged ahead with their impeccable Lester-Arrieta-Hendricks trio, adding Lackey and Quintana along the way.

However, as I noted above, the Cubs are now at a crossroads with their rotation. They are, perhaps more importantly, also at a crossroads in terms of their contention window. By all accounts, the Cubs will be good in 2018: favored to win the division, riding on the backs of Kris Bryant and Anthony Rizzo’s prime seasons while hoping for bounce backs from a handful of players, young and old. It’s hard to picture them as the World Series favorites as they were in 2016, though, as the Dodgers remain a staunch opponent in the NL, and the Astros and Yankees make moves toward becoming Fully Operational Battlestations. Considering the Cubs’ own contention window, which will likely begin to close in 2020-2021 as their young stars depart for free agency, the Cubs have no better time than now to improve their on-field squad and take advantage of a uniquely weak NL playoff picture.

We’ve set up a neat dialectic here, and a nice timetable to boot. The Cubs would improve their rotation greatly, and therefore improve their playoff chances, by adding an ace free agent starter; the difference between Chatwood/Montgomery and Darvish/Arrieta could be anywhere from two to four wins. Lester will likely perform more like a middle-of-the-rotation arm the next three years (or four, if his 2021 option vests). The Cubs will have tens of millions of dollars come off the books in 2020 or 2021 that they will then be able to spend on retaining their stars or signing new stars to anchor their club into the next decade.

This is why I think it would be smart of the Cubs, and other contending teams who sign starters to six- or seven-year contracts, to sign another ace free agent starter about midway through that first starter’s contract. With the knowledge that a 30-year-old pitcher will decline in the back half of such a contract, a team needs to replace that production somewhere. Unless a club has a ready pipeline of aces flowing into the majors—an unlikely scenario for a team in contention—then the only ways to add a top-of-the-rotation pitcher are to trade for one or sign a free agent. With the trade market for starters as stingy as it is, the latter option becomes the most expedient and effective for a team with few tradeable prospects. By the time this second free agent starter begins to decline and their production needs to be replaced, the first starter’s contract will have expired or have been traded, and the club will be free to add another starter to pick up the slack.

This might feel a bit rote, or too neat, but for a team like the Cubs, with essentially limitless coffers (and really, this applies to every team since revenues are in the hundreds of millions of dollars), it’s a sound strategy for both prying a contention window wide open and keeping the contention window open for longer.

When Jon Lester takes the mound for the first time in 2018, we won’t know exactly what to expect from him. He could be entering the twilight phase of his career, continuing to battle the injuries and fatigue he experienced in 2017, providing solid innings but never reaching his five-WARP heights again. He could return healthy and immediately make everyone foolish for doubting his skill, admirably holding his own in a rotation with two other aces. What we do know for sure is that the Cubs would be significantly better in 2018 and beyond with another ace in the mix, and there hasn’t been a better time to add one than this offseason. So, continue to sound the alarm every few years, Cubs—it’s best to get on top and stay there.

Lead photo courtesy Jerry Lai—USA Today Sports

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