DraftKings MLB DFS Picks – October 23rd

Well, here we go.

After a lengthy season (that somehow flies by), we have reached the World Series, and what a dandy matchup we have on our hands.

The Dodgers and Red Sox were long looked upon as the best teams in their respective leagues, although the Red Sox were underdog in the ALCS against Houston. Nonetheless, we have some serious star power in this one and it shouldn’t take long for this series to get entertaining, likely in a hurry.

Let’s double down on the entertainment factor by nailing some DraftKings MLB DFS Picks on this Tuesday night to get this World Series started on the right note.

Let’s go!

FLEX – Clayton Kershaw (LAD) – $14,000 vs. BOS

I really don’t think Chris Sale is going deep into this one as he hasn’t pitched more than 5.1 innings since the end of July, so Kershaw is the best bet to log significant innings in this one, something I want to give my lineup a solid foundation. The left-hander shook off a tough Game 1 start in the NLCS against the Brewers to hurl seven innings of one-run ball to go along with nine strikeouts in his most recent effort. The southpaw has struggled a little bit in his postseason career with a 4.09 ERA this time of the year, however this year he has flipped the script and pitched to a 2.37 ERA across 19 innings so far in these playoffs. Going up against this Red Sox offense is going to be difficult, and the Kershaw’s Dodgers are +136 underdogs in this Game 1, but I believe here is some longevity and strikeout upside here while I also think the Dodgers pull the Game 1 upset to boot, possibly landing Kershaw in the win column.

FLEX – Manny Machado (LAD) – $9,400 vs. BOS

Chris Sale won’t be long for this game in my opinion, which makes Machado a great play as he has hit both lefties and righties fairly evenly this season, making him matchup proof later in the game. What also makes Machado a nice play tonight is the fact he had posted an .813 OPS in the postseason, but more importantly with a .500 SLG, three homers and two doubles with nine RBI so far. Machado is going to be at the center of the drama in this one as he’s had a rather controversial postseason so far, but Machado also isn’t afraid to let his bat do some talking as well, something he did in the NLCS win over the Brewers. Finally, let’s keep in mind Machado has the second-largest sample size on the Dodgers against Sale and it’s a productive one. He has gone 6 for 19 (.316) with a homer, two doubles and two steals against the left-hander. I’ll take that production any day of the week.

FLEX – David Freese (LAD) – $6,800 vs. BOS

Freese just seems to know how to get it done this time of the year as evidenced by his career .883 postseason OPS. Of course, much of that damage came earlier in his career when he was a postseason hero while with the Cardinals, however Freese is coming off a huge effort in Game 6 against the Brewers. In that contest, Freese homered and doubled to give him a .300 average and 1.033 OPS across 12 plate appearances in these playoffs. It’s likely Freese gets the nod at either first base or DH tonight, most likely the former with Max Muncy likely to DH. Freese is a respectable 2 for 5 with a walk in his career against Sale but is also projected to hit in the three-hole, a very valuable spot in the lineup. Therefore, he technically leads off our four-man stack against Sale and the Red Sox ‘pen.

FLEX – Matt Kemp (LAD) – $6,400 vs. BOS

Kemp might get replaced defensively when a right-handed pitcher comes in for Sale, however I will roster Kemp in the hope that he can do some damage in a couple at-bats against the left-hander. After all, Kemp clobbered lefties to the tune of a .235 ISO and .828 OPS in the regular season, a season in which the players voted on him as a finalist for comeback player of the year. It hasn’t been a productive postseason for Kemp so far as he hasn’t started a game since Game 2 of the NLCS. That said, he should see fairly low ownership as a result and I think he can park one over the green monster in left field against a left-handed pitcher tonight.

FLEX – Brian Dozier (LAD) – $6,500 vs. BOS

Dozier hasn’t accomplished a whole heck of a lot since coming over from the Twins at the trade deadline, but tonight could be his night to shine against a pitcher he has seen a ton over his big league career. Dozier has logged 50 plate appearances in his career against Sale while he’s gone 12 for 47 (.255), but with three homers and four doubles as well, good for a big .277 ISO and .832 OPS against the southpaw. Dozier should get the nod at second base in this one, and although he had a tough overall year at the plate, games like this are why the Dodgers went out and paid a price for him at the deadline.

FLEX – Steve Pearce (BOS) – $6,200 vs. LAD

This is a little bit of a GPP play as I am taking a hitter against my pitcher, but with the way Pearce has hit lefties and performed in these playoffs, I wouldn’t mind seeing a solo shot from the veteran, even if it’s off of Kershaw. Between the Blue Jays and Red Sox this year, Pearce clobbered left-handed pitching to the tune of a .255 ISO and .959 OPS. In these playoffs, Pearce has produced an .810 OPS with a homer and a double across 26 at-bats. He is also 1 for 2 with a double in his career against Kershaw. He comes at cheap price, and although I think Kershaw enjoys a productive night tonight, I think Pearce has the ability for some one-off pop in this matchup tonight.


Brenton Kemp / Author

Brenton is a lifelong sports fan who resides in Ontario, Canada. Brenton is a fan of most all sports but specializes in hockey, baseball, football, basketball, and golf. He’s a fierce researcher with a strong appetite to deliver accurate and relevant facts that in turn have led to past success with picks and DFS advice across the board. Brenton’s biggest goal is to deliver readers with the picks and advice that can build their bankroll. He takes great pride in his success and loves nothing more than to share that success for the benefit of everyone involved.