The Yankees can’t figure out Dallas Keuchel

Thursday night’s loss to the Astros came down to an incredibly entertaining finish, one which almost needed extra innings to decide the outcome. Gary Sanchez ripped a single in the shortstop hole to drive in a run, but the tying run in Jacoby Ellsbury was gunned down at home plate. Game over.

Or was the game over once the Astros starting pitcher was announced? The Yankees were able to make a game of it thanks to Michael Pineda settling down and keeping the Astros’ potent offense at bay. Once again, however, the Bombers’ bats were painfully silent against southpaw Dallas Keuchel.

The Yankee Killer hurled six innings of shutdown ball, using every bit of his repertoire to rack up nine strikeouts and just one walk. This was the latest edition of Keuchel owning the Yankees. Perhaps the most painful chapter of this frustrating book coming in 2015 when Keuchel pitched a shutout and sent the Yankees home from the AL Wild Card Game.

With this most recent outing, Keuchel now boasts an ERA of 1.24 against the Yankees over 50.2 innings of work. He has looked unhittable this season, but also unhittable against the Yankees over the past couple of years. The Bombers just can’t seem to figure him out, no matter how many right-handers with which they stack their lineup.

Keuchel isn’t alone. There have been a few pitchers over the years who have been a thorn in Yankees’ sides for most of their careers. Most of the names you remember are obvious choices given their resumes on the hill, but let’s look anyway.

Hoyt Wilhelm

Wilhelm was a thorn in the Yankees’ side starting in the late 1950’s. That couldn’t have been as painful as Wilhelm pitching with a piece of metal in his back. The knuckleballer suffered the injury while serving the country during World War Two, but pitched through the injury over his entire career.

The metal didn’t seem to effect the Hall of Famer when he took the mound against the Yankees. Wilhelm threw 209 career innings against the Yanks, and retired with a 1.98 ERA against them. This was while working around hitters like Mickey Mantle, mind you. The Yankees won a few World Series in that era, but could never figure out the Giants pitcher. Granted, Wilhelm did most of his damage from the bullpen, but the numbers are still staggering.

Roy Halladay

Raise your hand if you were relieved when Doc Halladay left the AL East for the Phillies. Looks like everybody has a hand up, as you should. Halladay owned the Yankees as a member of the Blue Jays. Wins for a pitcher don’t mean too much, but it just seemed like he picked up a win EVERY time he faced the Yankees. The fact that the team seemed to run into him every other week was nauseating.

Halladay left the American League with an ERA of 2.84 against the Bombers. That was best among starters in the Wild Card era who threw at least 100 innings against the Yankees. They were able to pounce on Halladay for six runs over six innings once the Doc faced them as a member of the Phillies, but I’m sure nobody wanted to face him again.

Cliff Lee

Speaking of the Phillies, let me just get this guy out of the way quickly. I saved up a whole bunch of money to go to my first World Series game ever in 2009, only to see Lee shut the Yankees down and give us fans in the Bronx absolutely nothing to cheer about aside from player introductions. The Yankees wound up winning the series of course, so that helped a little, but still.

Amazingly, Lee’s dominance over the Yankees only continued the following year, this time as a member of the Rangers in the ALCS. Lee pitched eight shutout innings against the Yankees in a pivotal game three, and struck out 11 batters. What made this worse was that Lee was close to becoming a Yankee that year, so maybe the Bombers have 28 rings had a trade been finalized. Cashman had the right idea by trying to acquire Lee, because the Yankees could never do anything against him.

Chris Sale

Let’s stick with the left-handers here and look at a guy who has cut through Yankees’ lineups over his career like it was a throwback jersey. Sale joined the Red Sox this offseason, having gone 10-1 against the Yankees for his career, complete with an ERA of 1.17. That was the lowest mark for a pitcher with at least 50 innings pitched against the Yankees in a century.

His first start against the Bombers was basically business as usual. Sale fanned 10 over eight innings, but did allow two runs while the Red Sox lost the game thanks to a gem by Masahiro Tanaka. The Yankees escaped that time, but Sale still looks to be a nightmare for Yankees hitters, especially now in a Red Sox uniform.

Frank Lary

Coined the “Yankee Killer” around the time of Wilhelm’s dominance, Lary compiled a record of 28-10 against the Yankees from 1955-61. He averaged almost five runs per game of support from his Tigers teammates, but his ability to beat the Yankees was impressive nonetheless.

Lary beat the Yankees seven times in 1958, and even beat them with his bat in 1961 by stroking a game-tying triple in the seventh inning of the Tigers’ home opener. Detroit went on to win the game, but Lary suffered a leg injury while legging out that triple which altered his pitching motion from then on. He was never the same again.

Were there any pitchers that you feared? Do any stand out as especially tough on the Yankees? Let us know in the comment section below.