MLB DFS picks and pivots: September 25, the Night of Lester

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CHICAGO, IL – SEPTEMBER 27: Jon Lester #34 of the Chicago Cubs walks down the dugout stairs during the game against the Pittsburgh Pirates at Wrigley Field on Thursday September 27, 2018 in Chicago, Illinois. (Photo by Rob Tringali/MLB Photos via Getty images) /

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Looking back through history there are certain battles in times of war, across sports and even in fictional characters that have set the bar for what a true championship toe to toe match-up looks like.

We all remember the great Ali-Frazier fights and how they compared to the on-screen battles between Rocky and Apollo. As kids, we laughed as the Roadrunner outsmarted Wile E. Coyote on Saturday mornings, and now as grown-ups, we fight the daily battle of real-life versus just wanting to stay in bed and watch cartoons.

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These all-time classic battles have really set the stage for one final battle, one that Picks and Pivots readers have been waiting for with bated breath and eager bankrolls – well today for the final time in 2019 we get Jon Lester versus Brian Tulloch.

Lester is the Roadrunner to my Wile E. Coyote. I spend hours pouring through FanGraphs pages, digging into game logs, certain that tonight is the night I finally get him and as I kick back and turn on the TV, I get reminded of his wizardry as barrel alerts go off on my phone, but on the TV they are right at Cubs fielders.

Just once, we need Wile E. Coyote to win right?

Well, tonight is the night kids – and disclaimer, if it is not, just wait until 2020 because you can be certain I am going to be using the same silly Lester pitchers and stacking up every 5 days against him!

We have all been waiting for it this season, the Lester regression train, and since the beginning of August, this train has been consistent in pulling into the station as 5 of his last 10 starts have resulted in 5 or more ER’s. However, in true Jekyll and Hyde fashion, Lester has given up 1 ER or less in 4 of those starts so this is about as boom our bust an arm you can target hitters against and for some reason he tends to boom more than bust when he is on slates we can stack against him.

Now the Pittsburgh Pirates are not exactly an offense we go out of our way to target and with this game being in PNC Park with a pitcher’s umpire behind the plate, it could end up being Jonny Boy’s last chance to crush my soul before we head to the NBA season.

Conversely, this Pirates stack is a cheap right-handed heavy stack that allows you to easily build around a deGrom/Bieber lineup which all silly narratives aside, is really what you should prioritize. Since the beginning of August, Lester’s 5.1 SIERA is the 12th worst in baseball and on this slate, only Jeff Samardzija has been worse, so you are targeting an arm that has been among the worst qualified starters in baseball for nearly the last two months and you have a 50% success rate in that time of blow up starts – once again making stacking against Lester a true coin flip.

The Pirates top 6 in the projected lineup – Newman, Reynolds, Reyes, Osuna, Diaz and Tucker – are all dirt cheap with Reyes, Tucker and Diaz all under $6K on FantasyDraft which again, makes them the ideal stack if you want to fire up double-barrel aces this evening.

The definition of insanity is doing the same thing over and over again and expecting different results right? But hey – one last time with feeling – HAPPY JON LESTER Day all!

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