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The 2019 World Series Will Be a Spectacular Free-Agent Showcase

Gerrit Cole, Anthony Rendon, and Stephen Strasburg will likely be the top three players on the market this winter. Can anything they do help—or hurt—their earning potential?

Getty Images/Ringer illustration

In the top of the first inning of World Series Game 1, almost-unbeatable Astros starter Gerrit Cole will face Nationals third baseman Anthony Rendon. In the bottom of the first inning of World Series Game 2, Nationals starter Stephen Strasburg will pitch to the top of the Astros’ lineup. And just like that, everyone watching—Nats and ’Stros supporters, envious fans of the other 28 teams, and general managers making their offseason shopping lists—will have seen the best talent that the 2019-20 free-agent market may have to offer.

The 2019 Fall Classic is a matchup between one of the best teams ever and an NL opponent that’s matched it win for win since late May; between two of the greatest rotations ever to tangle on the World Series stage; and between a team that’s going back for World Series seconds with its current core and a franchise that’s still searching for its first title. But it’s also a showcase for Cole, Rendon, and Strasburg, three Scott Boras clients who may be weeks away from becoming the free-agent market’s top trio.

Narratively speaking, it seems somewhat premature to fixate on free agency before the first pitch of the Series; the climax comes before the falling action. And while these two teams are pitted against each other in a high-stakes scenario with a one-for-all-and-all-for-one ethos, it’s slightly distracting to dwell on the inevitable breakup of their rosters, even though free-agent turnover happens for righteous reasons (players getting paid what they’re worth and choosing where they want to work). Clearly, Cole (29), Rendon (29), and Strasburg (31) all have more immediate matters on their minds than where they’ll be playing next season and how much richer they’re going to get. They’ve starred in the postseason so far, ranking first, fourth, and 18th, respectively, in postseason win probability added (or first, third, and 26th in championship win probability added), and Strasburg would place higher if his gem in NLCS Game 3 hadn’t come in a contest with a lopsided score. All three have vital work to do for their current employers before they figure out who their future employers will be.

That said, the season will be over sooner than we’d like, and MLB wastes little time in transitioning to hot stove mode. The free-agent market moves slowly these days, but it technically opens as early as ever. Eligible players become free agents the day after the World Series ends, which starts the clock on a five-day period during which teams can negotiate exclusively with their own free agents. At the end of that span, bidding can begin, although free agents who received qualifying offers from their teams have 10 more days to decide to accept or reject them.

Cole is certain to test the open market, and Rendon is nearly a lock. Although the Nationals hope to bring him back and reportedly floated a seven-year, $210 million-$215 million extension (including deferrals) in September, it doesn’t seem likely that Rendon will accept that deal. The Nats could sweeten it before competing teams are allowed to talk to him, but at this late date, he has little to lose by entertaining other offers.

Strasburg is the least likely to become available, but he’s put himself in position to cash in. Under the terms of the seven-year extension he signed in May 2016, he’s signed for four more years and a total of $100 million, but his contract includes opt-outs after this season and next. After last season, when he posted the highest ERA and FIP of his career and spent time on the injured list with shoulder inflammation and a nerve impingement in his neck, Strasburg didn’t seem likely to exercise the opt-out this year, but his circumstances have improved significantly since then. In 2019, the formerly fragile Strasburg (who’s made nine career trips to the IL) led the NL with 209 innings pitched and, counting the postseason, has surpassed his previous single-season high. His peripherals were roughly in line with his pre-2018 standards, although Baseball Prospectus’s deserved run average says he’s having a career year. (Strasburg posted the best park-adjusted DRA of any pitcher with at least 70 innings pitched.)

Boras and the Nationals have long enjoyed a fruitful relationship, although they clashed at times during the Bryce Harper saga last offseason. Strasburg has already chosen once to stay in D.C. instead of exploring his options or trying to orchestrate a return to his native West Coast, and Boras hasn’t really ramped up his hype machine in preparation for a Strasburg bidding war as he has with Rendon. In late September, Boras said, “I make it a practice to not discuss anything with players about their contracts until they’re done performing, and certainly we’ll have time to address that and I’m sure Stephen will give me direction on it.” He’ll have to make his mind up quickly.

According to a poll posted earlier this month, roughly 53 percent of the MLB Trade Rumors reader hive mind expects Strasburg to opt out, 27.5 percent expects him to use the opt-out as leverage to wrangle an extension with the Nats, and less than 20 percent expects him to stand pat. If anything, the middle percentage seems a little light; as’s Mark Feinsand wrote on Sunday, “the feeling within the industry is that Strasburg … will leverage the opt-out into another year or two on the back end of his current deal,” as Clayton Kershaw did in a similar situation last year.

If Strasburg does opt out, he’d take the bronze behind Rendon and Cole on a list of the best free agents available. If we add up 2018-19 Baseball-Reference WAR totals for each of this year’s potential free agents, only J.D. Martinez (yet another Boras client) could edge out Strasburg. (Baseball-Reference WAR doesn’t factor in framing, which knocks out Yasmani Grandal.) Martinez has an opt-out, too, although for him the calculus isn’t as clear. As a 32-year-old DH coming off a less great season than the preceding two and facing a market that’s not kind to older, defensively limited players, he might not be able to beat the $62.5 million he’s slated to earn over the next three years by much (though he’d get $2.5 million just for exercising the opt-out). At the end of September, he sounded amenable to moving on.

Even if Martinez were to opt out, Strasburg would be the more appealing player. If we count him as the third-best free agent, then this winter’s top trio amassed 31.6 WAR over the past two seasons. Here’s how that stacks up against top free-agent trios of the past, going back to the beginning of free agency in 1976:

WAR-wise, the Rendon-Cole-Strasburg trifecta would be the best since 2015’s Zack Greinke–Jason Heyward–Johnny Cueto class, although it’s roughly in line with the 44-year average of 30.0 (which includes some strike-shortened seasons). Three top trios have cleared 40 WAR: 1992 (Barry Bonds–Greg Maddux–Lou Whitaker), 2000 (Alex Rodriguez–Mike Hampton–Manny Ramírez), and 1998 (Kevin Brown–Randy Johnson–Bernie Williams). Naturally, there’s more to a free agent’s appeal than what his WAR was in the past two years: Age matters, too, as well as how much of his production came in the contract year, how he’d performed in the past and, to some extent, star power.

What makes this moment so extraordinary, though, isn’t that these three constitute an abnormally talented trifecta of free agents; it’s that they’re all assembled in the same series, on baseball’s biggest stage, just days before their careers take a turn. The top three free agents in any given year are usually among baseball’s best players, and pennant-winning teams aren’t short on talent, so it’s not unusual for the World Series to feature one of the year’s top free agents; Manny Machado made it with the Dodgers just last year. We’ve even seen two of the top free agents in the same World Series, in 1981 (Ron Guidry and Reggie Jackson), 1998 (Brown and Williams), and 2011 (Albert Pujols and C.J. Wilson, who were on opposite sides in that series but would both soon sign with the Angels on the same December day). All three in the same series hasn’t happened, but it might this year.

Boras must love the way this has worked out, because the World Series stage can’t be beaten as a way to raise a player’s profile and display his skills. His three prize potential free agents have looked like franchise players this postseason. Rendon posted OPS marks above 1.000 in the Nationals’ first two post-wild-card series, driving in a combined seven runs after leading the majors in RBI during the regular season. Rendon may no longer be criminally underrated, but he’s still not properly rated by the public at large; his FanGraphs WAR over the past three seasons virtually ties him with Christian Yelich for third place among position players behind Mike Trout and Mookie Betts, but he hadn’t made an All-Star team until this year. Rendon doesn’t play loud, but it’s tough to play quiet in the World Series, when every action is amplified.

Strasburg, who’s allowed four runs in 22 innings this October (all in the NLDS), has already demonstrated his October excellence: His 1.10 career postseason ERA entering this week is the fourth-lowest of any pitcher with at least 40 postseason innings pitched, behind Mariano Rivera, Sandy Koufax, and Christy Mathewson. Another solid start or two could cement his legend. Cole has been even better this month, allowing one run in 22 ⅔ innings. The Astros have won 16 consecutive Cole starts, and opposing hitters have no solution to his high-spin stuff. The big righty’s full-season stats speak for themselves, but there’s still something to be said for seeing him slice through playoff lineups as if they’re the 2019 Tigers, touching triple digits and dropping devastating breaking balls.

Injury aside, there’s little these players could do in one series—even this series—to significantly sway front offices’ valuations, which are based on bigger samples. As one team analyst told me this week, “Nothing that happens in six games is really indicative of anything.”

Yet when MassLive’s Chris Cotillo surveyed several GMs last winter about the impact of postseason performance on free agency, most suggested that a big October was worth something. Maybe they were wary of sounding like automatons and merely paying lip service to the power of postseason success. Cold and calculating as they can be, though, GMs are human, and although they know recency bias exists, they aren’t immune to it. When a GM is weighing whether to devote a large portion of his team’s projected payroll to one player—and, by extension, link his own job security to that player’s performance—he almost can’t help but be soothed if he’s just seen that player excel in a high-pressure spot against great competition. Boras also sometimes does an end-around on the front office and appeals directly to owners, who may be even more susceptible to the notion that the best way to win is to import players who have rings or sterling postseason résumés.

There’s another way in which the outcome of this series could sway the fates of these free agents. Pennant-winning teams tend to be fairly evenly matched, but even so, World Series winners during the wild-card era have tended to keep their rosters intact to a greater degree than World Series losers. That could be because teams that just went all the way hate to break up the band, and because the halo effect of a successful series colors a club’s perception of how much regression may be in store. The Red Sox would have been less likely to re-sign Steve Pearce and Nathan Eovaldi after last season if the former hadn’t hit three homers against the Dodgers and won the World Series MVP award, and the latter hadn’t thrown scoreless eighth innings in games 1 and 2 and then pitched six-plus self-sacrificial innings in extras in Game 3.

The performance of Pearce and Eovaldi in 2019 (combined WAR: -0.5) underscores the danger of decisions based on small-sample postseason success. But there’s nothing unreliable about the records of Rendon, Cole, and Strasburg. We are not uncertain that those guys will make baseball teams better in 2020. This series is a chance for them to show the world why one more time before rival organizations try to woo them.

Soon we’ll be wondering whether Strasburg will opt out and what it would take to convince him not to. We’ll wonder whether Cole will secure the biggest contract ever for a free-agent pitcher; even in these dark times for free agents, elite players get paid, and Cole should become the fifth pitcher to join the $200 million club. We’ll also wonder how close to Cole’s total Rendon will come: 64 percent of MLB Trade Rumors readers say Cole will land the bigger payday, but the eight-year, $260 million extension Nolan Arenado signed in February may be on Boras’s mind. Arenado is younger than Rendon, but he signed his extension a season before free agency, and he’s not as good: By FanGraphs WAR, Arenado’s best season would be Rendon’s fifth-best.

For now, though, we’re wondering who will win the World Series. We already know who will win after that: Cole, Rendon, Strasburg, and Boras, in one way or another.

Thanks to Kenny Jackelen of Baseball-Reference for research assistance.