Here are my guidelines: By "pitched well", I mean pitchers who pitched on a regular basis most of a season and were average or better at doing so. So I’m looking for pitchers who, at least, started 20 games or pitched in 40 with an ERA+ of 90 for a starter or 100 for a reliever. We’ll go through the list according to how old each pitcher was when he last achieved such decency. The slash stat will their July 1 age/year. I will skip the interesting details about the pitchers already discussed in earlier articles – although I may embellish a bit more on Moyer and others as it relates to their careers after turning 42. 

Jack Quinn (48/1932) is the man Moyer is on target to top as the oldest to pitch well. Quinn turned 49 at mid season in a year he led his league is saves – for the second year in a row. Those were Quinn’s first two seasons as a full-time reliever after a two-year transition. In his age 44/45 season of 1928, he had a more outstanding season as a starter than did Moyer at 44 or 45. 

Moyer is trying to leap over three other pitchers with good seasons in their latter 40s:

·         Hoyt Wilhelm (47/1970) – amongst the oldest ever & a Hall of Famer

·         Phil Niekro (47/1986) – the HoF-er Moyer hopes to top as oldest starter who "pitched well" for a season.

·         Satchel Paige (46/1953) – HoF & all-time oldest appearance 

As I write this, 49-year-old Jamie Moyer (45/2008) has a 96 ERA+ and a 4.66 ERA in his first seven starts of 2012. We are a long way from assuming a 49-year-old with that start will make it onto our list. It is impressive nonetheless that he topped all but four pitchers with 2008 season: 16-7 with a 3.71 ERA (117 ERA+) over 196 innings as a 45 year old. He is up here among Hall of Famers, great knuckleball pitchers and spitball pitchers. However, as you will see, it’s not just knuckleballs or spitballs or Hall of Fame ability that preserves your arm enough to continue to be effective well into your 40s. Command of any softer-thrown pitch can be sufficient. 

Moyer gets by with a four-seam fastball, a two-seam sinking fastball, a cut fastball, a curve, slurve, and change-ups. His fastest fastballs have never actually been fast (mid 80s) by major league standards. They are only getting slower (high 70s). Right now, there aren’t many major league pitchers who can’t throw, at least, 91 miles per hour. I recall reading somewhere that other than knuckler R.A. Dickey, Moyer is by far the slowest. His career strikeout rate (per 9 innings) in the majors is 5.4 with an ERA of 4.23.  He has never led the league in a significant pitching category, although from 1998-2003, he did have five outstanding years with the Mariners (with one down year in the middle). 

Charlie Hough (45/1993) – knuckleball thrower amongst the oldest ever

Nolan Ryan (45/1992) – Hall of Famer mentioned amongst the oldest ever

Jesse Orosco (45/2002) – oldest career reliever since Wilhelm

Randy Johnson (44/2008) – HoF

Gaylord Perry (44/1983) – HoF – birthday is Sept. 15 – five days after Randy Johnson’s

Warren Spahn (44/1965) – HoF – his OPS+ was only 89, but it was 107 after he escaped the Mets to pitch for the Giants.

Dutch Leonard (44/1953) – a typical late-arriving, long-lasting starting-or-relieving knuckleball pitcher. Leonard’s prime was his first four years with the Washington Senators, from ’38-’41 at the ages of 29-32. After a broken ankle derailed his career in ’42, Leonard gradually came back to top form by 1945 at age 36. In ’44 and ’45, 72% of the Senators’ starts were by knuckleball pitchers. Mickey Haefner, Roger Wolff, and Johnny Niggeling were the other knuckleballers in their rotation. Leonard had two more outstanding years with the sad sack Phillies of ’47 and ’48. They traded him to the Cubs, where a year later, he was turned into a reliever for the last four years of his career.

Tommy John (44/1987)

Roger Clemens (43/2006) – HoF – only 19 starts, but a 194 ERA+, so he obviously belongs here. With only 17 starts at age 44, but a 108 ERA+, he just missed qualifying above Randy Johnson.

Joe Heving (43/1944) – sidearm sinkerball pitcher led the A.L. in appearances after turning 44 in the World War II season of 1944. Heving’s 1.96 ERA with 120 innings was a career year. A pertinent quote from Heving can be found in The Neyer/James Guide to Pitchers which takes the quote from Gordon Cobbledick in the Baseball Digest of May 1943:

You know what kind of pitcher I am. I throw a side arm fastball that sinks. Well, I’ve noticed that on the days when I seem to be a little faster than usual my sinker doesn’t break and I get my ears pinned back. So I’m satisfied to go along with just medium speed, and if I lose some more of that as I get older maybe it’ll make my sinker still better.

Red Faber (43/1933) HoF / grandfathered spitballer like Quinn.

Diomedes Olivo (43/1962) –one of the original three Dominican pitchers to debut in 1960. His chance came at age 41, making him the second oldest rookie ever—perhaps  the oldest, depending on Satchel Paige’s real age. The other two pioneer Dominican pitchers were Rudy Hernandez (age 29) and Juan Marichal – the future Hall of Famer, then only 22. Only catcher Ozzie Virgil (Sr.) and outfielder Felipe Alou preceded these pitchers from the Dominican Republic.

As I write, a total of 542 Dominican players have made it since –about twice as many non-U.S. born players as from anywhere else over the history of the major leagues. Olivo was a lefty who threw a fastball, curve, and change-up. I don’t know how hard he threw, but he had a 9.31 strikeout rate as a 41-year-old. Olivo was similar to Paige in another way: he has been called a legend. Olivo was a national hero from the Dominican Republic who had won that country’s Most Valuable Player award 6 times. Put him on your list of greatest players most people have never heard of.

Cy Young (43/1910)

Doug Jones (43/2000) was another soft tosser known for his change-ups – not to be confused with Todd Jones, who was another soft tossing righthander and contemporary of Doug who pitched in the majors at 40. Just to remind you, Doug Jones’ prime years were initially with the Indians from ’87 to ’90, and his his best year was with Houston in 1992. He had another excellent year with Philly before the strike in ’94, then another fab year for the Brewers in ’97. Jones finished quite respectfully at age 42 and 43 with Oakland in ’99 and ’00. Todd Jones pitched well for the Astros ’93-’96 and the Tigers ’97-’00 and then again ’06-’07, but his one excellent year was with the Marlins in 2005.

Sad Sam Jones (42/1935) turned 43 in July of 1935 when he produced a 114 ERA+ in 19 starts and two relief appearances. Jones was known for a curve, a slow ball, and a fastball. His best year was way back in 1921 for the Boston Red Sox as a 28-29-year-old. He was 23-16 in 299 innings with a 3.22 ERA. His nickname was bestowed upon him by a sportswriter trying to rhapsodize poetically, who only knew Jones from the distance of the press box and unaware of the typical sparkle in his eye.

Tim Wakefield (42/2009) –another knuckleball pitcher. Wakefield did finish 8-1 in 13 starts after his July 31 debut with the Pirates as a 25-year-old in 1992. He continued as their pitching star in the NLCS, winning both of his starts with complete games. However, the Pirates lost the Series and Wakefield lost his mastery of major league hitters. By early July the next year he returned to the minors and didn’t resurface until the end of May in 1995 with Boston. Once again he impressed by going 16-8 in 195 innings (in 2/3 of a season), and a 2.95 ERA in a hitters’ year in Fenway (165 ERA+). He spent 17 years in Boston as the Red Sox’ adaptable 5^th or 6^th starter. That is the longest pitching gig of any Boston pitcher ever – N.L. or A.L.

Dolf Luque (42/1935) was the first Cuban pitcher to pitch in 100 games, 1000 innings, (add your own milestone). He was the major leagues first Cuban born pitcher and, in fact, the major leagues’ only Latin American star until the 1950s. At least Luque (LOO-kay) got to pitch in the prime of his career in the States.  Yet, he was a late bloomer. With his combination of fastball and dropping curve, Luque won a league-high 27 games after turning 33 in 1923, adding a league-low 1.93 ERA. He won the ERA title again two years later. Despite only making 35 appearances, he makes this list as a 42/43 year old reliever due to his 2.69 ERA (120 ERA+) and his continued effectiveness for another season plus two more flawless appearances as a 44 year old. For eight years of Luque’s prime, he averaged 262 innings per season – but that was just in the States. "The Pride of Havana" also played in the top Cuban league during the winter for 34 seasons – up through the age of 46.

From the age of 23 through 36 (’84-’97) John Franco (42/2003) was consistently one the National League’s top relievers: 6 years with Cincinnati, then 7 with theMets. He was still useful the next four years with the Mets, but not enough to keep his closer role. In 2002, Franco had Tommy John and Flexor Tendon surgery and managed to come back just a year later in May of 2003 at the age of 42. Franco pitched in 38 games and compiled a 162 ERA+ and ERA of 2.62. Brooklyn-born John Franco was baseball’s oldest pitcher the next two years while Dominican-born Julio Franco was baseball’s oldest player. According to Baseball-Reference, John Franco is Mariano Rivera’s second most similar pitcher at age 41 (after Trevor Hoffman). Franco’s pitch repertoire featured a sinking fastball (in the high 80s at the end of his career), a circle change-up, and a slider. Franco is the career Saves leader for a left-hander.

Dennis Eckersley (42/1997)

Jim Kaat (42/1981) - another four-decade player. Kaat’s top weapon was a slider– still major-league worthy (95 OPS+) at 44. Kaat won 16 Gold Gloves, but his golden years as a pitcher were at ages 26 and 27. In ‘65 Kaat was 18-11, 2.65 in 264 innings, plus three starts against Sandy Koufax in the World Series. The next year, Kaat was 25-13 and 2.75 in 305 innings. Kaat’s 13 straight years with the Senators-Twins is the 17^th longest stint with one team – just missing my previous list of the longest tenured pitchers.

Don McMahon (42-44/’72-’74) is more deserving than Mulholland, Ryba, or Heving of this list, but he didn’t technically qualify. McMahon had 44 appearances at age 42, but he was a little below the 100 ERA+ mark. However, if you blur his last three years together, you get a clean 3.00 ERA (123 ERA+). He accomplished this as the Giants’ pitching coach – one of MLB’s last player-coaches. A fastball pitcher with a complimentary breaking pitch, McMahon didn’t reach the majors until he was 27. He spent his first five seasons with the Braves, pitched for six other teams over the next eight years, and then settled with the Giants for his last five.

It came as a surprise to me that Jeff Fassero (42/2005) makes this list. My recollection of his career extends from his 1993 highly successful conversion to starting as a 30-year-old by Expos manager Felipe Alou to a sudden drop in ability six years later in Seattle. I forgot that he lasted eight years as a below-average journeyman lefty long reliever and fill-in starter. He played for eight different teams during that span. His best year among his last five came at age 42, when he had a better-than-average 4.05 ERA in 91 innings.

Is Fassero comparable to C.J. Wilson? Fassero is a 6’1" lefty who made the conversion during his age-30 season. Wilson is also a 6’1" lefty and made the change at age 29. They have had similar strikeout rates, walk rates, and groundball rates. According to the Neyer/James Guide . . ., Fassero threw a sinking fastball, forkball, slider, and a change. From what I can tell from FanGraphs, Wilson throws a low 90s fastball (it probably was a two-seamer as he has a high groundball percentage), a cutter, a curve, a change-up, and occasionally a slider. So, they are very similar, but perhaps Wilson’s cut fastball will ensure a longer productive career than Fassero’s forkball did.

Grover "Pete" Alexander (42/1929) - HoF

Terry Mulholland (42/2005) –a lefthander with a slider, change, and a few fastballs – including a split-fingered version. According to Neyer/James Guide to Pitchers, Mulholland "was almost impossible to run against". Mulholland pitched for 12 different major league teams, including three stints with the Giants. He had four consecutive years as a solid Phillies starter ages 27-30, then lost his sinking fastball when he was traded to the Yankees. From there on, he was the epitome of a journeyman: 10 teams in 12 years and only a 91 ERA+/ 4.85 ERA. However, he did manage to put up a 4.27/105 ERA+ in his final year.

Earl Caldwell (42/1947) – has the distinction of peaking in his early 40s. Certainly, his age 40 and 41 seasons were by far the best of his major league career. His age-42 season hits the minimum criteria for making this list: exactly: 40 games and 100 ERA+. Caldwell spent most of his 20s and 30s in the minors, but it appears he pitched his best from age 36 until he retired at 49. Caldwell had a sidearm/near-underhanded delivery. His SABR Bio explains why he enjoyed such late-career success by quoting him, "Well, my fast ball -- while not fast -- has got more stuff on it than it ever had. It’s a sinker and makes the hitters top it often and hit on the ground, so there’s a better chance for double plays. I don’t know why it breaks better than it ever did. I just tinkered with it through the years and finally stumbled on the knack of doing it."

Woodie Fryman (42/1982) didn’t start his professional career until he was 25. He was a Kentucky tobacco farmer content to play in his amateur Blue Grass League on the weekends when the Pirates signed him. A year later, 1966, he was in Pittsburgh’s starting rotation. After two years there and four and a half years with Philadelphia, Fryman was put on waivers. Detroit snatched him up and in the last 8 weeks of the season Fryman won 10 games, lost 3, and compiled a 2.06 ERA (154 ERA+) over 114 innings. That was his career highlight as it led to a division title for the Tigers.

Fryman also did very well in his two stints with Montreal--especially after Dick Williams turned the lefty into a reliever. At 40, Fryman’s ERA was down to 2.25, then at 41 even lower: 1.88. He was still pitching just shy of league average for 70 innings and 60 games at 42, so I felt he deserved inclusion in this list of old masters. Early in Fryman’s career, he was considered a strikeout pitcher: fastball, change, and slider. As he got older, especially as a reliever, he relied on getting ground ball outs.

Greg Maddux (42/2008)

A relatively light skinned Cuban named Conrado "Connie" Marrero (42/1953) didn’t come to the U.S. to play baseball until shortly before he turned 39. He was a well-established superstar in his own country. That was in 1950 – fifteen years after Dolf Luque last pitched in the majors. The Washington Senators had a farm team in Havana, where Marrero  dominated for the three years leading up to his American League debut. According to Baseball-Reference Marrero is still alive at age 101 – the oldest living ex-major-leaguer at this moment.

At age 40, Marrero was the ace of a very bad Senators team and a fixture in their rotation for the surrounding four seasons. According to Felipe Alou, as quoted in the SABR Bio Project, the 5’5" curveball/change-up control pitcher "had a windup that looked like a cross between a windmill gone berserk and a mallard duck trying to fly backwards". The height, the curve ball, and the wind-up are not characteristics we would normally associate with a pitcher lasting well into his 40s . . . nor would Marrero’s infamous fondness for long cigars be indicative of a centurion. Dare I say his legendary greatness during his career in Cuba along with notoriously quotable chutzpah and his old age success in the majors entitles him to be dubbed the Satchel Paige of Cuba.

David Wells (42/2005) – known for his curve ball and control, controversial comments, and for changing teams 13 times … and a large tattoo of a loved one (as a child) on his right arm and an extremely elaborate tattoo of Babe Ruth batting against Wells on his pitching arm. Wells was extremely consistent from ages 27 to 42.

Mike Ryba (42/1945)–Ryba is another pitcher who peaked in his 40s. Along with a few call-ups, the Cardinals gave Ryba a full season in 1937 at age 34, but he was sent back down the next year. He didn’t get back to the majors until 1941. He was 38 by that time, but he stuck with the Red Sox for the next 6 1/2 years. No doubt the War helped, but he was clearly an improved pitcher. His development was slowed because he was also a catcher; in fact, he was a regular catcher until 1935. He caught in the majors on rare occasions until 1942.

In his 20s and early 30s, Rick Honeycutt (42/1996) was a fragile starter who sometimes relieved. In1983 he led the American League in ERA for the notoriously pitching-starved Rangers, while getting traded out of the league for the last six weeks of the season. In 1987 at age 33, Honeycutt was traded to Oakland where manager Tony La Russa and pitching coach Dave Duncan converted the slider/fastball starter into a situational lefty reliever. This revitalized his sagging career.

By 40 Honeycutt tried his luck with the Rangers again, this time yielding an ERA of 7.20. So, the next year Honeycutt went back to Oakland, where La Russa and Duncan straightened him out. That September, the Yankees needed a lefty for their wild card run and bought Honeycutt. For the Yankees, he produced a 27.00 ERA. The next year La Russa and Duncan moved to St. Louis and the Cardinals appropriately signed Honeycutt. For one last fine year, at age 42 Honeycutt produced a 2.85 ERA (a huge 148 ERA+ in that hitters’ era) over 61 appearances.

The surprisingly extended careers in recent decades of Kaat, Fryman, Honeycutt, Orosco, Franco, Fassero, Mulholland, Wells, and Moyer has fed the myth that lefties are so special that they can stay employed longer than righties. There may be some truth in that, but I sense it is an exaggeration. Case after case, the pitchers who last the longest relative to the greatness of their peak years tend to have great command of some lightly tossed pitches in their arsenal.

The way Darren Oliver is pitching – and the way Miguel Batista is not pitching so well, I’d expect Oliver to be the next pitcher to make this list. He is 41, so he has to maintain this level for another year and three-fourths. Jose Contreras is the only other 40-year-old still active – other than Moyer and Mo, of course. For a dozen years Oliver scratched out a career as a 4^th or 5^th starter. In 2006 at the age of 35, after a year of being released by two teams and not even cracking the majors, the Mets turned Oliver into a reliable long relief lefty. The Dodgers took him for the next three years. Texas has had Oliver the last two years as one of the most effective short-use lefties in baseball. Son of the Kansas City Royal / California Angel corner infielder–outfielder Bob Oliver, Darren seems to have abandoned his curveball and change-up in favour of a sinking fastball and slider. He tried throwing a cutter during his first year with the Mets. It seems that another helpful attribute for late career success is being able to adapt.

To sum up the pitches that seem to allow a pitcher the longest success, obviously a knuckleball is tops, followed by a spitball. Two-seam fastballs and cut fastballs seem to give the arm more years than a four seam or split fingered fastball. Throwing a slider without snapping the wrist seems to be a better choice of a breaking pitch for longevity than a curveball, which is probably better than a screwball. A circle change appears to be a better choice than a standard change-up – unless you have command of a knuckler.

So, how many pitchers were shining as brightly as Mariano Rivera at 41 or older? One dozen. Ranked by WAR in their best year past that age: 

1. Cy Young
2. Roger Clemens
3. Randy Johnson
4. Warren Spahn
5. Nolan Ryan
6. Jack Quinn
7. Phil Niekro
8. Ted Lyons
9. Hoyt Wilhelm
10. Connie Marrero
11. Satchel Paige
12. Pete Alexander