Justin Steele's opening day start is a long time coming for the Cubs

Their history of drafting lefty pitchers is even worse than you've ever dreamed

Justin Steele's opening day start is a long time coming for the Cubs

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When Craig Counsell announced that Justin Steele would be the Cubs’ opening day starter it was an obvious choice. Steele is the Cubs’ best pitcher, he is coming off an All-Star season where he won 16 games had the lowest home runs allowed per nine innings in the National League (0.7) and finished fifth in Cy Young Award voting.

So that part of the announcement wasn’t all that noteworthy.

The footnote to the announcement was.

Steele is the first left handed pitcher drafted by the Cubs to get an opening day start for the team.

Huh?

That can’t be right. The Cubs have been drafting players for 59 years. Surely, one portsider that they picked made an opening day start for them. Right?

Uh…no.

In those 59 drafts the Cubs have selected 310 lefthanded pitchers.

Only 54 of those have pitched as many as one game in the big leagues.

And until March 28 of this year, ZERO of them will have pitched opening day for the Cubs.

Hell, hardly any lefty the Cubs have drafted has started an opening day for anyone. Except the Mariners. Cubs lefthanded pitching draft picks have made seven opening day starts in the 46 year history of that franchise.

Five lefty Cubs draft picks have made opening day starts in the bigs for somebody and the one made with the most is probably a guy you didn’t know the Cubs ever drafted.

Mark Langston was the Cubs 15th round pick in 1978, but he chose to go San Jose State instead. He ended up making seven opening day starts in his career, four for the Angels and three for the Mariners.

The other Mariner is Jamie Moyer, who the Cubs drafted in the sixth round in 1984. At least he actually pitched for the Cubs. Not well, but he did make 79 starts in just three seasons, going 28-34 with a 4.42 ERA. He left in that big 1989 trade that included Rafael Palmeiro and Mitch Williams. And then pitched 21 more seasons in the big leagues.

In 1969 the Cubs drafted Joliet’s very own Larry Gura in the second round. He pitched four mostly undistinguished seasons for the Cubs before he was the player be named later in a 1973 trade with the Rangers for the immortal Mike Paul. Gura then got traded to the Yankees for Duke Sims (not Steve Yeager’s character in Major League, we’re not sure if Duke Sims ever threw at his own kid in a father-son game) and then found a home when the Yankees traded him to the Royals in 1976 for catcher (and eventual squeaky voiced Mets announcer) Fran Healy. With the Royals, Gura started on opening day twice, and finished in the top ten in American League Cy Young voting three times.

On May 28, 1985 his career came full circle when he signed back with the Cubs as their pitching staff was falling apart, especially the rotation, as all five starters eventually landed on the DL at the same time. Gura made four starts and was released in August with an ERA of 8.41.

Speaking of famous trades (we were just doing that a few paragraphs ago about Jamie Moyer), the only other Cubs lefty draft pick to make more than one opening day start was traded from the Cubs to Marlins before the 2003 season in a deal to get Matt Clement and El Pulpo, Antonio Alfonseca.

Dontrelle Willis was Rookie of the Year, an All-Star and a World Series champion his first season with the Marlins and made two opening day starts in his Florida career. His best overall season was in 2005 when he was 22-11 with a 2.63 ERA. But the next year he led the NL in walks and things were never the same. He was also part of a big trade when the Marlins made the Tigers take him in the eight player deal that landed Miguel Cabrera in Detroit.

And finally, and most ironically, the best lefthanded starter the Cubs have ever drafted who actually pitched well for them was the first lefthanded pitcher they ever drafted.

Ken Holtzman was the Cubs’ fourth round pick in the first Major League Baseball draft, ever. His 27.3 WAR is by far the most by a Cubs lefthander they drafted and who played the majority of his career with them. And, of course, he made his lone opening day start in 1972, for the Oakland A’s.

How pitiful have the Cubs been at drafting lefty pitchers?

Between Larry Gura in 1969 and Craig Lefferts in 1980 they drafted 47 lefties, only seven ever pitched a single inning in the majors, and the only ones who posted career WAR of more than one were Dave Geisel (2.3) and Langston (50.1) and they combined to make just 36 appearances for the Cubs (all by Geisel, obviously).

The first time they drafted more than one lefty in the same draft who pitched in the big leagues was the first draft with Holtzman and 11th rounder Tom House (better known for being a pitching coach who had his pitchers throw footballs to warm up.) House didn’t sign with the Cubs.

The next time they drafted more than one lefty in the same draft who pitched in the big leagues was 19 years (YEARS!) later when the 1984 draft produced Drew Hall (taken third overall) and Moyer.

It happened again the next year when Joe Kraemer and Doug Dascenzo were picked in the same draft. I’m not sure if Dascenzo counts since he was an outfielder, but he pitched five scoreless innings for the Cubs in his big league career.

From 1986 to 1996 the Cubs drafted 65 lefty pitchers, only five of them ever pitched in the big leagues and none of them posted a positive WAR.

One of them, Lance Dickson, was drafted in the first round June 1990 and made his big league debut on August 9 of that same season after just eight minor league starts. He made three starts for the Cubs, went 0-3 with a 7.24 ERA, blew out his arm and never pitched in the big leagues again.

In 1993 the Cubs drafted 15 (FIFTEEN) lefty pitchers and only one of them pitched in the bigs, and it wasn’t for the Cubs. Matt Miller was their fifth round pick, didn’t sign, was a second round pick of the Tigers three years later and pitched 10 career innings in the majors.

Their best back to back years of drafting lefties were 2002 and 2003 when Jim Hendry drafted Rich Hill (‘02) and Sean Marshall (‘03). Hill has a career WAR of 16. And it’s only taken him 19 years to do it. Marshall was a useful pitcher for six seasons, but is probably remembered by most Cubs fans for boring us to death on Marquee’s pre and postgame shows and for getting traded for Travis Wood1.

In 2009 the Cubs drafted Brooks Raley and Chris Rusin, both had inexplicably long careers and no one has ever been able to tell them apart. Raley, (Or is it Rusin? It’s Raley. I think.) incredibly is still pitching for the Mets. He washed out of the big leagues, went to Korea for five seasons and came back in 2020 and is still truckin’.

Hendry tried very hard to draft a good lefty, using 63 picks from 2001 to 2011 and only hitting on Hill, Marshall, Jerry Blevins (best known as a Cub for being traded for Jason Kendall), James Russell (was kind of good in his first Cubs stint and came back to make a cameo in 2015), and, I guess, Raley and Rusin.

But Theo Epstein shouldn’t make fun of Hendry’s efforts. His Cubs used 35 picks from 2012 to 2020 on lefties and all they have to show for it is Rob Zastryzny (-0.1 WAR) and, now, finally, Steele.

I guess Theo can brag that he drafted the only lefty to start an opening day for the Cubs (provided Steele stays healthy for two more weeks.)

Steele has only pitched three seasons so far, but in the long, storied history of Cubs lefthanded starter draft picks, he’s already tied for tenth in career WAR. And that includes the guys who didn’t even sign with the Cubs!

Here they are.

  1. Mark Langston (15th round, 1978) 50.1 WAR
  2. Jamie Moyer (sixth round, 1984) 49.8 WAR
  3. Ken Holtzman (fourth round, 1965) 27.3 WAR
  4. Larry Gura (second round, 1969) 21.4 WAR
  5. Dontrelle Willis (eighth round, 2000) 19.7 WAR
  6. Rich Hill (fourth round, 2002) 16.0 WAR
  7. Scott Downs (third round, 1997) 10.8 WAR
  8. Sean Marshall (sixth round, 2003) 9.3 WAR
  9. Craig Lefferts (ninth round, 1980) 8.9 WAR
  10. tie - Jerry Blevins (eighth round, 2004) and Justin Steele (fifth round, 2014) 6.3 WAR

Just for fun, the Cubs traded Scott Downs twice.

In 1998, the year after they drafted him he was the player to be named later in an August waiver deal for Mike Morgan. How the hell was their third rounder from the year before worth five starts, no wins and a 7.15 ERA from Morgan? But that’s fine. Ed Lynch had also traded away his 1996 (Todd Noel) and 1997 (Jon Garland) first round picks over a span of three days that July for Felix Heredia (a lefty!) and Matt Karchner. Both Heredia (a.k.a. The Run Fairy) and Karchner were awful.

But Downs came back just months later in a May trade with the Twins along with Rick Aguilera for Kyle Lohse and Jason Ryan.

Downs would eventually be traded away for good in a 2000 deadline deal with the Expos for Rondell White.

White was a great hitter whose career was cut short by the awful turf in Montreal (even more than Andre Dawson’s was).

You want me to bring this full circle?

Guess who was taken one pick ahead of Rondell in the 1990 draft?

Lance Dickson.

You can’t make this shit up.

The Cubs history of drafting lefties in the first round is woeful. They’ve done it seven times. those pitchers have combined to pitch in 49 games for the Cubs. And 45 of those are Drew Hall’s with a 6.41 ERA.

The first round lefties are a Who’s Who of Who?
Brian Vernoy (1972), Vance Lovelace (1981), Drew Hall (1984), Lance Dickson (1990), Luke Hagerty (2002), Mark Pawelek (2005) and Brendon Little—not Luke—(2017).

But hey, we have Justin Steele now, and who knows, maybe Jordan Wicks will be good, too?

Well, let’s not press our luck too hard.


  1. I remember him mainly for being a more than solid pitcher and for the time in Cincinnati for the Cubs when he almost got thrown out at first base on a ball that hit the outfield wall and Lou Piniella nearly ripped the dugout bench off its bolts.