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.
The On Deck Circle 
A Mets Post Mortem
Let me begin by congratulating the Kansas City Royals on their first World Championship season in 30 years. I also want to acknowledge my pre-season error when I predicted that the Royals were probably a fluke last year, and would be unlikely to repeat as A.L. champions this season. The Royals appear to be a team whose sum is greater than the whole of their individual parts, but baseball being a team sport, they were well-constructed and expertly managed.
As for the Mets, the Royals did a fantastic job exposing and exploiting each of their weaknesses. Specifically, a team built around starting pitching will probably be most vulnerable once those starting pitchers are removed. In this day and age, when complete games are largely a thing of the past, this means that a bullpen cannot, then, play second-fiddle to a young and talented starting staff.
There needs to be a virtually seamless level of pitching talent from the first through the ninth innings. After all, major league baseball is not a seven inning game. If the manager signals, time after time, that he would rather trust his tired starters to pitch an inning longer than they should probably be allowed to instead of going to fresh bullpen arms, (and worse, if he allows himself to be talked into doing so by his spirited starters), then the final third of every game will inevitably become the Achilles heal of what should be a strategic advantage.
If I’m putting too fine a point on it, use the damned ‘pen at the beginning of an inning, not once an overworked starter has inevitably put a man or two on base.
The Mets infield defense is sub-par, and it’s difficult to imagine, quite frankly, how the Mets made it this far in the playoffs with not one above-average defensive infielder. If your pitchers have to strike out eight to ten batters per game to keep the ball out of play (at least as far as the infield is concerned), you are A) forcing your starters to throw too many pitches through the first six innings to gain those 4-7 pitch strikeouts (vs. those one or three pitch ground-outs), and B) you are allowing the defense to become too comfortable, so that when a ground-ball is hit, the fielders are potentially less ready to make the play.
I love Danny Murphy for his bat, and yes, even though his homer total during the first-two rounds of the play-offs was fluky, the man can hit. But an actual second-baseman (as opposed to a hitter who happens to play second-base) would be preferable to the current option. If Murphy is allowed to move on elsewhere as a free agent, I would have to count that as a potentially positive move for the Mets, IF it results in an over-all improved infield defense (no sure thing at this point)
With the advent of sabermetrics, especially over the past fifteen years or so, a new orthodoxy has taken over most baseball teams. Don’t run much, forget the sacrifice bunt, go for the long-ball, and take your walks.
Oddly, though, the original premise of (at least Billy Beane’s version) of sabermetrics wasn’t so much to enshrine any particular strategy as baseball’s version of the New Testament. It was to exploit those aspects of baseball being neglected by your financially wealthier opponents. Which aspects of a given player’s skill-set were being undervalued, and how could a relatively poor team exploit those undervalued skills in the baseball marketplace?
Mets General Manager Sandy Alderson was (at the helm those aforementioned A’s teams) one of the earliest proponents of this philosophy of baseball, and translated to the (oddly) mid-market Mets, this philosophy has appeared to pay dividends in 2015.
Yet, as the Kansas City Royals have shown, there is apparently more than one way to win a World Championship. The Royals offensive strategy, such as it is, is to play a kind of pre-1920’s baseball, when putting the ball in play, running with apparent abandon, and disrupting the other team’s game-plan (arguably the bete noire of sabermetrics) becomes the whole point of the game.
In other words, perhaps the movement of modern baseball G.M.’s to (at least appear to) embrace particular tenets of sabermetrics has become the new, already calcifying religious orthodoxy that, in turn can be exploited by a small market, 21st-century ball-club. In effect, meet the new boss, same as the old boss.
While there is not necessarily a correlation between age and the ability to adapt to new realities, it is worth raising the point that with Sandy Alderson turning 68-years old later this month, and manager Terry Collins reaching his 67th birthday next May, are they the right men to have at the helm of a team composed of players who could be their grandchildren? Will they be able to objectively evaluate the structural deficits of this team through the baseball lens of 2015, or will their baseball strategy perpetually reflect an era that might already be coming to an end?
Obviously, the payroll level Mets ownership settles on during this off-season will go a long way towards defining this team’s future, both immediate and long-term. What can they afford to pay, for example, outfielder Yeonis Cespedes, and what will his asking price be? Certainly, Cespedes uninspired post-season performance (12 hits in 54 at bats with one walk and 17 strikeouts) won’t help drive up his asking price, but do the Mets commit a very substantial chunk of payroll to him, pursue a different free agent outfielder, or go another route altogether?
Meanwhile, while it would certainly be tempting not to tamper with that young, talented pitching staff, would it make sense to trade one of those arms for a highly talented position player? After all, as we saw in this World Series, a solo homer here or there is perhaps not the best way to achieve a balanced offense.
Finally, from a Mets fan point of view (and I’ve been one now for over 40 years), it should be noted that only two Major League teams were still playing meaningful baseball on November 1st, and the Mets were one of them. From that perspective, and for the happy memories this team provided for their fans of the playoff series against both the Dodgers and the Cubs, we have to count 2015 as among of our all-time favorite, most enjoyable baseball seasons.
Thank you, New York Mets, for all your efforts this season, and let’s look optimistically forward to the 2016 baseball season, as I’m sure baseball fans of every team will also be doing.
Let’s Go Mets!