The On Deck Circle

Baseball History, Commentary and Analysis

The Best Losing Pitchers of All-Time

Most pitchers who lost more games than they won in their careers did so because they just weren’t very good pitchers.  In fact, they were often just plain awful.  But there is an unusual subset of pitchers who were actually pretty good at their craft who still ended up with more losses than wins.  It may seem counter-intuitive, but it is true.  Some pitchers are just unlucky.

The original idea for this post came from my last post when I was examining the career of Jon Matlack. Matlack pitched 2,363 innings in his career, winning the N.L. Rookie of the Year award in 1972.  He retired with a career ERA of 3.18, an ERA+ of 114, and a career WAR of 38.7.

Overall, these are numbers that for most pitchers would normally have resulted in a winning record. Yet Matlack completed his career with a record of 125-126.  Although his peripheral numbers all indicate that he was a good pitcher, he still ended up with a losing record.

That got me to thinking about how many other pitchers there might have been in baseball history who pitched well at least as often as not, but never received their fair share of wins.

Before I started my research, I had to set some arbitrary ground-rules.  I decided that to make my list, a pitcher had to have at least 100 wins, 1,500 innings pitched,  at least 200 career starts, and he had to have a career ERA below 4.00.

My research has turned up (and I’ve probably missed some), several intriguing examples of “good” pitchers who retired with losing records.

Here are some examples of these pitchers, in no particular order, with a brief synopsis of their career highlights.

1)  Pat Dobson:  In 1971, Dobson posted a record of 20-8 with an ERA of 2.90 in 282 innings.  He hurled 18 complete games for the Orioles, and finished the season in the A.L. top 20 in MVP voting.  His ERA+ was 116.  The following season, Dobson led the A.L. in losses with a record of 16-18, despite an ERA of 2.65 and an ERA+ of 117.

Dobson would also go on to win 19 games with the ’74 Yankees, and in his seven seasons in which he tossed over 200 innings, he posted an ERA over 4.00 just twice.  He finished with a respectable career ERA of 3.54 in 2,120 innings.  Despite all of these positives, Dobson finished his career with a record of 122-129.

2)  Mark Gubicza:  Gubicza was a two-time All Star who enjoyed a Dobson-like 20-8 season with a 2.70 ERA in 35 starts with the Royals.  Although Gubicza had some trouble staying healthy in his 13 seasons with the Royals (1984-96), he did lead the A.L. in starts twice.

Gubicza also surrendered the fewest home runs per nine innings three times, and fewest walks per nine once.  In 2,223 innings pitched in his career, he posted a career ERA+ of 109, and a career WAR of 34.8, better than Hall of Famers Catfish Hunter and Rube Marquard.  He was, in most seasons, better than the average pitcher, yet accumulated more losses than wins.

3)  Bill Singer:  Twice in his career, in 1969 with the Dodgers and 1973 with the Angels, Singer won exactly 20 games.  In each of those two seasons, he also made exactly 40 starts, pitched exactly 315.2 innings, and hurled exactly two shutouts.  Also, in both seasons, he topped 240 strikeouts.  Strangely, he walked just 74 batters in ’69, then walked 130 in ’73.  Apparently, Nolan Ryan must have rubbed off on him.

Singer was an erratic pitcher, but, as you can see, he was quite dominant in his prime.  In 308 career starts, he tossed 2,174 innings, and his career ERA was a respectable 3.39.  It was a surprise to me, then, when I saw that Singer had finished his career with a record of 118-127.  He deserved better.

4)  Bob Friend:  Friend’s career is probably the most extreme example of this group of an excellent pitcher who got saddled with more wins than losses.  His 197 career wins are, by far, the most of any pitcher I could find who finished his career with a losing record (197-230.)  But his career win-loss percentage (.461) is actually one of the worst I could find among the players in his group.

Friend led the N.L. in wins with 22 in 1958.  Then he went on to lead the league in losses with 19 in 1959.  In 1960, he bounced back with 18 victories, then proceeded to lead the league in losses the following year once again with 19.

Friend led the league in games started three times, in innings pitched twice, in batters faced twice, and in ERA and ERA+ once each.  He pitched 200 innings every season from 1955 to 1965 for the Pittsburgh Pirates.  Friend’s career WAR of 48.9 is better than several pitchers in the Hall of Fame.

Friend, a four-time All Star, made 497 starts in his career, pitched in over 3,600 innings, and logged a career ERA of 3.58.  If he had pitched on better teams than the often dismal Pirates, he might have reversed his career record, and perhaps even some consideration for the Hall of Fame.

5)  Randy Jones:  Randy Jones won the 1976 N.L. Cy Young award for the Padres with a record of 22-14, led the league in starts (40) complete games (an astonishing 25), innings pitched (315) and WHIP (1.027).  Although he hardly ever walked anyone, it is also amazing that he struck out just 93 batters all season.

The previous year, Jones finished as the runner-up in the Cy Young voting to Tom Seaver.  Jones actually topped Seaver in ERA (2.24) and ERA+ (156) while posting a nice 20-12 record.  Interestingly, the season before these two consecutive excellent years, 1974, Jones led the N.L. in losses as he was saddled with a record of 8-22.

But Jones’ career went downhill rapidly from that point, his last semi-effective season coming in 1979.  Jones finished his career, spent almost entirely with San Diego, with a career record of 100-122, and an ERA of 3.42.  As far as I can tell, Jones is the only Cy Young award winner (among starting pitchers, and using the criteria I listed above) who finished his career with more losses than wins.

Now here are the rest of the pitchers who meet my standards, listed alphabetically, with their respective win-loss records, and their career ERA’s:

6) Jim Barr:  101-112, 3.56

7) Tom Candiotti:  151-164, 3.73

8) Dick Ellsworth:  115-137, 3.72

9)Woodie Fryman:  141-155, 3.77

10) Bob Knepper:  146-155, 3.68

11)  Jon Matlack – 125-126, 3.18

12) Rudy May:  152-156, 3.46

13) Fritz Ostermueller:  114-115, 3.99

14) Steve Renko:  134-146, 3.99

15) Jim Rooker:  103-109, 3.46

16) Zane Smith:  100-115, 3.74

17) Clyde Wright:  100-111, 3.50

A few other pitchers I looked at just missed making this list.  Danny Jackson, for example, had a career record of 112-131, but his career ERA was 4.01.  Nap Rucker finished his career with a perfectly mediocre record of 134-134, so he missed making this list by one loss.

Now, of the seventeen pitchers listed above, which ones were the best?

Let’s begin by eliminating all of those pitchers with a career ERA+ under 100.  Well, there goes Bill Singer (99), Bob Knepper (95), Woodie Fryman (96), Steve Renko (98) and Clyde Wright (96).

Now we are down to just twelve pitchers.  Using career WAR as a litmus test, let’s eliminate any pitcher on this list with a career WAR below 20.  Say goodbye to Pat Dobson (17.6), Randy Jones (19.7), Rudy May (19.6), and Jim Rooker (16.7).

We have eight pitchers remaining.  Let’s raise the bar a bit more to reward pitchers who pitched at least 2,000 innings.  That eliminates Zane Smith.  Let’s also knock off the lowest remaining ERA+, Dick Ellsworth (100).

Our six remaining pitchers are:  Jon Matlack, Mark Gubicza, Jim Barr, Tom Candiotti, Bob Friend, and Fritz Ostermueller.

Now let’s list our remaining six in order of career WAR, highest to lowest:

1)  Bob Friend – 48.9

2) Tom Candiotti – 41.0

3)  Jon Matlack – 38.7

4)  Mark Gubicza – 34.8

5)  Jim Barr – 30.5

6)  Fritz Ostermueller – 27.6

Eliminating Ostermueller, who has both the lowest WAR and the highest ERA (3.99), we have a nice little five-man rotation of Friend, Candiotti, Matlack, Gubicza and Barr.

The Black Ink test used by Baseball-Reference.com, that is, the categories in which a player led his league, highlighted in bold print, is still another way to measure a particular player’s value.

Using the Black Ink test, Bob Friend wins by a wide margin.  He scores a 20,  Matlack and Gubicza each score a 4, while Candiotti  and Barr each score a 2.

Therefore, I think it is clear that the best losing pitcher of all-time, as far as my research goes, was Bob Friend.  I would rate Jon Matlack as the runner-up, with either Gubicza or Candiotti in third place.

Congratulations to Bob Friend, the Best Losing Pitcher of All-Time.

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24 thoughts on “The Best Losing Pitchers of All-Time

  1. Chris Wagner on said:

    Add Matt Cain to ur list. Definitely top 10, maybe in your starting rotation.

  2. Cody Allen on said:

    Time to update the list, Matt Cain HAS to be top 5. Found this old article while trying to research Matt Cain’s greatness when he announced his retirement today.

    • For a half-dozen years or so, Cain was a horse. All those innings caught up to him by age 28, but he was a very fine pitcher while it lasted. You’re correct. He probably belongs among the top five best “losing” pitchers.

  3. Consider Ray Herbert W104, L 107, ERA 4.01. Was 4-0 with Detroit at the beginning of his career when he was drafted into the military in 1951.

  4. I can’t believe I missed this post until now. My brothers and I often argued about who was the best pitcher in Pirates history (not the most shining distinction in baseball history, I grant you), and I have always contended–for many of the reasons you list in this post–that Friend is the best pitcher in Pirates history.

    • Hey again, W.K., I do appreciate you going back and taking a look at that post. I’ve actually come up with several other pitchers who could have been on that list as well. Friend had an interesting career for both some very bad and some very good Pirates teams.
      Thanks again for reading,
      Bill

    • Hey Again, W.K. I appreciate you going back and taking a look at that post. I have since come up with a few other guys who should be on that list. Friend was interesting in that he played on both some very good and some very bad Pirates teams (mostly bad.)
      Thanks again, Bill

  5. Frank Tanana is a near miss. 240-236, 3.66 ERA

  6. I just brought up the best losing pitchers by WAR to see if there was anyone missed on the list.

    Bobo Newsom went 211-222 with a 3.98 ERA (107 ERA+) from 1929 to 1953.

    Jack Powell posted a 2.97 ERA (but the era made it just a 106 ERA+) while going 245-254. He pitched from 1897-1912.

    19th century hurler Ted Breitenstein was 160-170 while posting a 4.03 ERA (which actually came out to a 110 ERA+).

    Murry Dickson pitched from 1939-1959 and went 172-181 with a 3.66 ERA (110 ERA+).

    Danny Darwin is a recent pitcher (1978-1998) who went 171-182 with a 3.84 ERA (106 ERA+).

    Bob Rush pitched from 1948 to 1960 and won 127 vs. 152 losses (his .455 winning percentage is the lowest of anyone with 36+ WAR and a losing record). He had a 3.65 ERA with a 110 ERA+.

    There are several more, but I figured I’d share some other guys near the top of the list.

    • Hi Adam, I figured I’d missed a few. Another friend of mine emailed me the names Bobo Newsom, Bob Rush and Murry Dickson. As I said in my post, I knew I probably missed some guys.
      Of all the guys I missed, I’d say that only Bobo could arguably supplant Bob Friend as the best losing pitcher of all time. But it is interesting to see how many pitchers there have been over the years that were generally better than average, yet still posted losing records.
      Thanks for all the research, and for reading.
      Bill

  7. Great piece. I immediately thought of Friend when I saw the title.

  8. I’m a huge fan of Camilo Pascual (at 174-170 he can’t make your list), but he played a lot of years with awful teams (the late ’50s Senators). I remember Friend was like that, a good pitcher that pitched for some bad teams and never seemed to get much run support.
    It’s funny how that works. I remember somebody did a study of Koufax and Drysdale in the ’60s and determined the Dodgers averaged about 1.5 runs less per game that Koufax started (I think that’s right, I didn’t look up the exact figure). Maddux seemed to me to be the same way.
    Really nice research and a good job, as usual.
    v

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