The Pittsburgh Pirates had a decision to make heading into the final day of the 2014 season in Cincinnati: Use ace Gerrit Cole in game No. 162 or save him for the wild-card game against San Francisco. The Pirates were guaranteed a wild-card spot, but the division title was still up for grabs.

Pittsburgh was a game behind the St. Louis Cardinals in the NL Central. If the Pirates won and the Cardinals lost later in the afternoon at Arizona, they would play in a tiebreaker for the division the next day. Entering that Sunday, FanGraphs gave the Pirates a 12.8% chance of winning the division.

The decision was so difficult for Pirates manager Clint Hurdle that he asked a council of veteran players for their thoughts: Pitch Cole or save him? Pittsburgh already exhausted its second-best starter, Francisco Liriano, a day earlier. In speaking with Pirates beat reporters that weekend - myself included - Hurdle dismissed the idea of trying a bullpen game. We were still a few years from the Tampa Bay Rays popularizing the opener role or from the Oakland Athletics starting the 2018 wild-card game with reliever Liam Hendriks, the only attempt at a pure bullpen effort in a play-in game.

Pittsburgh elected to chase the division title. Cole dominated the Reds, but the Cardinals later won to clinch the division. The Pirates then tossed their sixth-best starter by WAR, Edinson Volquez, against the Giants and lost in the play-in game. Perhaps the decision didn't ultimately matter as Madison Bumgarner shut out the Pirates, beginning his historic postseason pitching run to lead the Giants to the World Series.

The Giants are one of only two clubs to win a title as a wild-card entry since the format began in 2012. The 2019 Washington Nationals are the other team. The Nationals used their co-aces, Max Scherzer and Stephen Strasburg, to cover the first eight innings in the play-in game.

Some teams in postseason chases this year could face similarly tough decisions. Getting to the postseason - ideally by winning the division - is, of course, the goal. But for teams that appear headed for wild-card spots, setting a pitching plan through the play-in game is crucial. So which contenders appear to be in the best shape in navigating their way to the play-in game and advancing from it?

First, we must underscore the importance of having an edge in starting pitching in the play-in game era. Of the 16 wild-card games played from 2012-19 (we're excluding last year's expanded postseason), the team that started the pitcher with the greater WAR won 14.

The winning teams started their first- or second-best pitcher by FanGraphs' WAR in 15 out of 16 games - pitchers who averaged 4.4 WAR in the regular season. The losers started their first- or second-best pitcher by WAR in 10 of 16 contests, and the pitchers they sent to the mound averaged 2.6.

Now, let's take a look at how this year's wild-card contenders stack up.

 

AL wild-card race

The Toronto Blue Jays, Boston Red Sox, and New York Yankees are all within half a game of each other, fighting for two postseason berths. (The Athletics and Seattle Mariners, who are three and four games behind, respectively, are long shots, according to FanGraphs.) Given the closeness of the AL wild-card race, the Jays, Red Sox, and Yankees might not be able to set their rotations as they'd like for the postseason.

In a perfect world, the Blue Jays would send Robbie Ray to the mound in a wild-card game on regular rest and not have to worry about anything. While not in so many words, the Jays essentially announced Friday that they're recalibrating their rotation to do just that. Ray's now lined up to pitch Sept. 20 at Tampa Bay, Sept. 25 at Minnesota, and Sept. 30 versus the Yankees, according to FanGraphs. That puts him squarely into an Oct. 5 wild-card game on regular rest. Toronto also has an off day Sept. 27 to further tinker with the rotation if needed.

Having multiple top-end starters is ideal to navigate this end-of-season path. It gives teams flexibility.

Jose Berrios, by WAR and FIP, is slightly stronger than anyone the Yankees or Red Sox can offer as a No. 2 option and is throwing the ball as well as just about any AL pitcher. Over the last month, Ray (No. 1) and Berrios (No. 4) rank in the top five in AL starting pitchers' WAR. Cole sits second and Boston's Nathan Eovaldi ranks third, though the Red Sox might prefer to line up Chris Sale.