Houston’s currently fighting for its life against Tampa Bay in the ALDS, but regardless of whether the Astros advance, they could be a few weeks away from losing one of their most valuable players to free agency. Right-handed ace and potential AL Cy Young winner Gerrit Cole is on the cusp of reaching the open market, where his forthcoming contract figures to easily outdo the majority of his competitors’ next deals. In fact, the lone soon-to-be free agent who’s likely to wind up in Cole’s stratosphere is Nationals third baseman Anthony Rendon. Both players are lining up for contracts in the $200MM range, which seems like an especially risky number for a pitcher. But how have those investments on pitchers worked out thus far? Let’s take a look at the few $200MM-plus guarantees given out to hurlers, keeping in mind that past successes or failures obviously do not determine whether Cole will thrive or fall flat once he receives his mega-contract…

David Price, LHP, Red Sox (seven years, $217MM)

  • Still the owner of the richest deal ever for a pitcher, Price hasn’t continued as an ace since he signed with the Red Sox entering the 2016 season. At that point, Price was a world-class run stopper who’d already logged five seasons with at least 200 innings. The Boston version has hit the 200 mark just once, though, and has put up a 3.84 ERA/3.74 FIP with 9.32 K/9 and 2.39 BB/9 across 588 frames. On paper, that production’s absolutely fine, but the Red Sox probably expected more when they splurged on Price almost a half-decade ago. Of course, thanks in part to Price, the Red Sox won the World Series a year ago. Flags fly forever.

Clayton Kershaw, LHP, Dodgers (seven years, $215MM)

  • Admittedly, it’s debatable whether we should count this deal. After all, Kershaw essentially opted out of it last offseason (when he had two years and $65MM left on the pact) in favor of a three-year, $93MM contract to stick with the Dodgers. No matter, Kershaw has been nothing short of outstanding since signing. Therefore, even if the eight-time All-Star and three-time NL Cy Young winner would have stayed with his previous contract, the Dodgers certainly wouldn’t have buyer’s remorse.

Max Scherzer, RHP, Nationals (seven years, $210MM)

  • Speaking of not regretting a $200MM-plus investment on a pitcher … we arrive at the Nationals, who are surely thrilled with the free-agent gamble they took on the ex-Tiger Scherzer going into 2016. Scherzer, who has been an All-Star every year and won a pair of NL Cy Youngs since then, remains among the game’s most imposing hurlers to this day. The 35-year-old’s fresh off yet another tremendous (albeit injury-limited) regular season and has been a key figure in what could be a stunning first-round playoff upset of the juggernaut Dodgers.

Zack Greinke, RHP, Astros (six years, $206.5MM)

  • Arizona poured its financial resources into Greinke entering 2016, though the headline-stealing addition didn’t quite pay off the way the club hoped. But that’s not a knock on Greinke, who excelled as a D-back. The team’s payroll just couldn’t support his ongoing presence, so it dealt Greinke to the Astros at this summer’s trade deadline. The 35-year-old, however, has enjoyed the latest terrific season of his career between the two organizations. Greinke’s $200MM-plus payday may not have been the most responsible move for an Arizona franchise that’s not a huge spender, but his production has been worthy of it.

If the above group shows us anything, it’s that no pitcher in the $200MM club has flopped (some have been great). That doesn’t mean Cole will follow in their footsteps if he scores a similar contract, but it’s hard to bet against a dominant, flamethrowing workhorse who still has another season in his 20s to come.

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