Although a driver who only made eleven starts and only won one of them at the Syracuse Mile may seem rather undeserving for a list of this nature, Snyder made a big enough impact before his death in an exhibition midget accident in Cahokia, IL to justify placement on the list as the first of several "what could have been" selections. Despite only making five starts at Indianapolis, he is still to this day 33rd all time in laps led in the race and in third place only behind Michael Andretti and Rex Mays in laps led among drivers who have not won the race. Additionally, although I am not completely sure due to the vagueness of the news reports I read, I am pretty sure that he was the TNL at Indy in both 1938 and 1939, making him one of only two drivers (along with Earl Cooper) to be the TNL in the Indy 500 multiple times and never win the race, indicating that he was very unlucky before dying young. Snyder competed in an era when there were usually only two or three races on the schedule, and in his breakout year of 1938 he was the TNL for both races that year at Indy and Syracuse. Despite competing in an era that wasn't diverse, he proved his diversity since he was capable of winning on dirt and theoretically capable of winning on a superspeedway given his potential for Indy dominance, even though it never happened. What cements his case for me is his 1939 Indy performance, where he won the pole setting a track record that would not be broken until 1950, led more laps than the winner Wilbur Shaw and was the TNL, while his Thorne Engineering teammate Mays was a relative non-factor qualifying 19th, finishing 16th, and leading one lap. Mays would go on to win the championships in 1940 and 1941, the next two seasons, finishing 2nd in both Indy 500s and winning all four of the other races on the schedule. Since Snyder beat Mays so handily when they were teammates and Mays was near his peak, I think he belongs on the list despite his minimal surface statistics.
After 1955 Indy 500 winner and champion Bob Sweikert left the dominant John Zink team, Sweikert was quickly followed by Pat Flaherty, Ed Elisian, and Larson in quick succession in 1956, with Flaherty scoring a repeat victory for the team in Indy and a 2nd straight win at Milwaukee before a critical arm injury at Springfield sidelined him for just over two years. Larson would make himself Flaherty's obvious permanent substitute for Zink with a pole on his debut at the Indiana State Fairgrounds and a win from pole in his second start at Sacramento. He would go on to become clearly one of the most dominant drivers on dirt in the late '50s, winning nine poles and five races and maintaining a career APL of over 10%, which isn't that common despite a relatively mediocre comeback in the mid-'60s after being suspended for medical reasons in the middle of the 1959 season during a race at Springfield where he was diagnosed with a heart attack (but this was later proven to be heatstroke long after the fact). However, despite his dominance on dirt for several teams (he would also score the first win for legendary car owner/mechanic George Bignotti at Phoenix in 1958) he was terrible in races on pavement, most notably failing to qualify for the 1957 Indy 500 despite the Zink team winning the previous two years in dominant fashion. He was generally regarded as undisciplined due to a hard-partying lifestyle and his unwillingness to learn the more smooth style that would allow him to adapt to races on paved ovals, as his primary goal seemed to be winning money to pay for his extravagant lifestyle more than winning itself. Flaherty and Larson are arguably flip sides of the same coin. While Sweikert was able to win and dominate on both pavement and dirt for the Zink team, Flaherty was just as good on pavement but weak on dirt, while Larson was just as good on dirt but weak on pavement. Both are clearly borderline selections. Flaherty's Indy 500 win carries a lot, but trying not to be biased to one track type over another, I have to note that Larson was more dominant in his discipline than Flaherty was in his and I think that decides it.
One of the best IndyCar drivers of the early '50s, Stevenson got his big break with car owner and Milwaukee Mile promoter Carl Marchese, who had won four races and earned back-to-back 2nd place championship finishes in 1948 and 1949 with driver Myron Fohr. Stevenson replaced Fohr at Springfield in 1949 and earned a 4th place finish on his debut for the team as a substitute when Fohr was sick. He was named Fohr's replacement when Fohr was fired after failing to qualify for several races in 1950. While Stevenson was a more consistent qualifier than Fohr was, he did not even lead a lap for the Marchese team in his two years for them, he would never qualify or finish better than 3rd, and even he missed a couple races in 1951, which actually makes Fohr look more impressive and suggests that the team itself was more likely the problem rather than their drivers (but I'll point out that qualifying on the dirt tracks was no mean feat, as superstars including Indy 500 winners and champions actually failed to qualify frequently in this period). Regardless, just because I think Fohr was probably better certainly doesn't mean I think Stevenson wasn't good. After leaving the Marchese team, Stevenson really came into his own by winning the 1952 championship driving a brand-new rookie entry for the first female car owner Bessie Lee Paoli. Although women at that point were not allowed to enter the inside portion of the Indianapolis Motor Speedway, she was still an active participant passing notes to her crew chief Clay Smith through the track fencing. Despite a poor Indianapolis finish, Stevenson would win at DuQuoin and Milwaukee and finish no worse than 7th the rest of the season to take the title. However, the team rapidly declined after Stevenson and Smith departed for the J.C. Agajanian team, which had won the previous year's Indy 500 with Troy Ruttman. Despite a surprisingly much more inconsistent season, he still claimed another win at Milwaukee in 1953 despite qualifying 17th and looked much stronger in 1954 when he claimed his fourth and final win at Milwaukee followed by three straight 2nd place finishes shortly thereafter before abruptly retiring from AAA Champ Car competition when he watched Smith be killed in a pit road incident. Stevenson did occasionally dabble in other forms of racing over the next years, becoming the first road course ringer to win a race in NASCAR (if you can really call him that when there were only oval races in his era of IndyCar racing), perhaps indicating he had greater potential for versatility than he actually showed (with three of his four wins coming at his hometown track of Milwaukee). Stevenson did make a comeback in the early '60s but despite driving for some successful car owners like Bob Wilke, George Salih, and Al Dean, never led any more laps after his return and finished no better than 6th, usually many laps down. Although he was probably one of the weaker champions against a united field, one can still argue he had potential he did not realize based on his early retirement. All that is enough for me to put him on the good side.
Among more recent drivers, there was no driver I spent more time equivocating about than Briscoe. His raw statistics when taken in a vacuum would obviously make him a lock for the list and he has many other things in his favor as well. Although I had him off the list quite frequently, I noticed that he won on all four modern track types (superspeedway, short oval, road course, and street course) and every single other driver who had won on all four of those track types I considered to be a lock. Since all his wins came after the split ended, he had the highest adjusted wins of any driver I even thought about excluding (7.71); Buddy Lazier and Scott Sharp may have had more wins but they definitely came against worse competition. His 10 TNL and 9.34 CRL also led all drivers on my bubble as well, which is why I did choose to list him. However, you have to make a discount considering almost his entire career was spent with Penske and Ganassi, while other drivers who may have been similarly talented or superior rarely got the opportunities to compete in top equipment for more than two or three years. His 2005 season clearly made him look worse than he was as he entered the season as Toyota's top F1 prospect beating among others Nico Rosberg in the 2003 Formula Three Euro Series) and left without a top five finish and fired by Ganassi, but since Scott Dixon finished 13th in points, its clear Ganassi's equipment was to blame for both (and Briscoe showed well as he was nearly as fast as Dixon on the road courses even if he didn't get the finishes). Briscoe raised his stock considerably after scoring a 3rd place finish at Watkins Glen in a one-off for the weak Dreyer & Reinbold team in 2006 and became Penske's heir apparent to replace Sam Hornish when he left to NASCAR after he signed with Penske's ALMS team and finished 5th in a Penske satellite operation at Indy in 2007. Despite the infamous pit road contact with Danica Patrick in the 2008 Indy 500, he took off by passing Indy winner Scott Dixon the next week to win at Milwaukee, and for the next season and a half was as dominant as anyone else on track, particularly in 2009 when he won two races and scored seven 2nd place finishes in an eleven race span to take a seemingly insurmountable point lead. However, at the penultimate race at Motegi in 2009, he caught a lucky break when a caution came out while he was pitting which would have likely given him the win and the championship as long as he started the finale at Homestead. Instead of cinching the championship, he had one of the worst championship chokes ever by crashing leaving the pits while his championship rivals Scott Dixon and Dario Franchitti finished 1st and 2nd and dropped Briscoe to 3rd in the points before Franchitti won the championship on fuel mileage. Briscoe never seemed to recover from his championship choke and had three very lackluster years with Penske, then even more miserable stints for Panther in 2013 and Ganassi in 2014. He showed signs of life and his most impressive performances in years in 2015 for the Schmidt team as a fill-in driver for James Hinchcliffe, but it was too late to regain the reputation he once had and he was back to sports cars full-time in 2016. Regardless, his stats alone not counting differences in equipment would probably put him in the 50-70 range depending on what you look at, and that seemed too big to ignore. He clearly jumped off the page compared to my honorable mentions, but I wasn't excited about it.
Robson had a slow start in his pre-World War II starts, failing to lead any laps, finishing only four of his nine races from 1938-1941 for a variety of teams (although he did show some promise with 4th and 2nd place finishes at the two dirt track races at Springfield and Syracuse), and having a generally weak Indianapolis record. However, all that changed when AAA reinstated racing after the war in 1946. Despite being considered a dark horse contender at Indianapolis relative to Ted Horn, Mauri Rose, and Rex Mays, the three biggest stars at the time, Robson outlasted them all to win in dominant fashion for Joel Thorne's Thorne Engineering team. The 1946 season was particularly odd because as racing was being reinstated after WWII AAA wanted to make sure there were sufficient entries and races after years of inactivity, so they included 71 dirt track/proto-sprint-car races, which they called 'Big Car' races on the schedule and it was here where Robson particularly shone. While Horn, Bill Holland, and Joie Chitwood won more of these events than Robson did, Robson still won five of them giving him a total of six on the season on two very different track types (brick ovals and dirt ovals), which Horn despite being about to begin an incredible run of three consecutive championships did not manage to achieve having not won at Indianapolis. Unfortunately, Robson was killed in a Labor Day crash in 1946, the year of his Indianapolis win, when he was unable to see Earl DeVore running low on the track at a very slow pace due to low visibility. Robson became the last defending Indianapolis 500 winner to die in a crash prior to his fellow Briton Dan Wheldon in 2011. Much of Robson's stats are unavailable because no good data for the Big Car races seem to exist now, but the one Indianapolis win (the only Champ Car race in which he led any laps) is not enough to make a legitimate case for him (I left many Indianapolis 500 winners off), but his ability to win both at Indy and on dirt tracks is.
Ayulo, along with Jack McGrath, were two of the poster boys for the early years of the roadster era at Indianapolis. Although Bill Vukovich would become the most celebrated driver of their period, Ayulo and McGrath got there first, each debuting in AAA championship cars in 1948 after transitioning together from local California racing leagues. Both drivers took particular pride in building their equipment themselves and both drivers stood out relative to many of their competitors despite not being a part of any of what were considered then the dominant teams. Ayulo only won two races in his final season in 1954 but he did so for a rather weak Peter Schmidt team for which future Indy 500 winners and champions Sam Hanks and Jimmy Bryan managed to earn mere 12th and 6th place finishes, and Ayulo himself would have a much stronger run than his teammate Pat Flaherty in the Indy 500 in 1953, who would go on to win the Indy 500 in 1956, qualifying 4th when none of those other 500 winners came close to that. As the roadsters slowly took over from the previous generation of cars, Ayulo showed more and more promise in the 1953 and 1954 seasons, winning two poles and scoring four second-place finishes in 1953, then adding two wins at Darlington and Milwaukee in 1954 and added another three 2nd place finishes (although he also failed to qualify for three dirt races). Although roadsters were primarily used on superspeedways, Ayulo was no slouch in dirt races either, as he earned six of his seven 2nd place finishes in those races and all his poles, indicating that he likely would have exploded into dominance in the following seasons after 1954. Unfortunately, a fatal crash in Indianapolis practice in 1955 robbed him of his obvious potential (and brutally, his roadster buddies Vukovich and McGrath would both die before the 1955 season was over as well). His most noteworthy race came in 1954 at Milwaukee where he earned his only terminal natural lead in a fantastic duel where he and Chuck Stevenson exchanged the lead eight times, and even though there was no way Ayulo's Peter Schmidt team was any match for Stevenson's Agajanian team, which was one of the main powerhouses of the time, he hunted Stevenson down to take the lead in the final ten laps. Two of the biggest IndyCar stars of the 1950s, Johnnie Parsons and Tony Bettenhausen, failed to qualify for Schmidt at Milwaukee two years before and two years after Ayulo's win there respectively for the same team at the same track. It does make one wonder what he could have achieved if he had lived long enough to make it to a top team (or progress as an engineer enough to make his own team a top team).
Oldfield is one of the most famous drivers - maybe the most famous driver - from the first decade of American motorsports. Oldfield won the first AAA-sanctioned IndyCar championship in 1905 (if you can call it that since this was years before the Indianapolis Motor Speedway was even a thought in Carl Fisher's mind), is regarded by many to be the first professional race car driver in US history, and won his championship in dominant style by winning five of the seven races he started. He finished 5th in both of his Indianapolis 500 races, including 1914, when he was the top American driver behind four entries in greatly superior French equipment. His career as a driver sounds great on the surface. However, I believe what he was really known for and what he should be regarded as is more of a showman than a race car driver. Most of what he did came in private exhibitions, one-on-one match races, and speed record attempts. His speed record attempts were truly legendary for the era, as he was the first driver to run a mile a minute at the Indiana State Fairgrounds, he unofficially broke Victor Hemery's world land speed record, and became the first driver to achieve a lap greater than 100 mph at Indy. He wowed crowds with barnstorming speed exhibitions like the auto racing equivalent of the Harlem Globetrotters (albeit decades prior to them) and earned a reputation as the star of early American racing which still stands. While without question he was the pioneering driver of motorsports entertainment, that hardly means he was the best driver in general, and his record in his IndyCar starts does not support this. While he did win five of his seven starts in the first American open wheel season, what that overlooks is that none of these races lasted more than ten miles, none had more than three cars start them, Oldfield was the only starter in two of them, and none of the other starters in the races he won that year ever won a race themselves. The only other driver who did win races outside that season was Louis Chevrolet. In the only race Chevrolet and Oldfield both started, Chevrolet won. This was clearly the weakest season in terms of competition in American open wheel history. When the series did have much deeper competition in the late 1900s and 1910s, he was merely good, but nowhere near as dominant as other drivers of that time like Chevrolet, DePalma, and Earl Cooper (although he did sometimes beat them in exhibition races). His rank vs. contemporaries of two instead of one is really not a good sign for that era, especially when you consider how he had no real competition in 1905, his adjusted points per race are the lowest of any driver on this list, and his adjusted wins among the lowest. None of these are really good signs for evaluating him as a driver. He did win all his races on dirt in 1905 and both races on road courses in 1915 (one of which was a four hour race) indicating some measure of his diversity, and seven races in general, but if you ignore his championship season and look at everything he did in the deeper seasons he really doesn't look that impressive. He was a master at setting records by himself or in one-on-one match races, but in deeper fields, too many other drivers had similar credentials. I guess how you view him depends on whether you view him as the prototype for Evil Knievel or the Stig (legendary daredevil) or the prototype for Mario Andretti or A.J. Foyt (legendary driver). I'm in the first camp, but I still thought it would be rude not to include him on the list.
Any discussion of Luyendyk must begin by noting that he was probably the best Indy 500 driver of the 1990s. Although he was never on the very best teams, his races went as follows: 1990: 1st, 1991: 3rd, 1992: crashed while running 2nd, 1993: 2nd, 1994: non-factor, 1995: unlapped himself on the last lap to finish 7th, 1996: running 2nd when he got wrecked while leaving the pits by Eliseo Salazar, 1997: 1st, 1998: had a mechanical problem while running 2nd, 1999: crashed while leading. That is stellar. Few drivers had runs that consistent even if they didn't get the finishes over an entire decade at Indianapolis and he would be a lock for me just as much as he would for most others for a top 33 Indy 500 drivers list. However, this is not only about Indianapolis, and it is the other races where he wasn't as stellar. Although he is technically listed as the 1990 USAC champion when USAC sanctioned Indy and CART sanctioned everything else, when it came to full championship seasons in either CART or the IRL, he never actually attained a top five points finish. Almost every other driver in this list has, and Luyendyk had a lengthy career with a lot of full-time seasons. Even career-winless drivers of his era like Raul Boesel and Davey Hamilton got top five points finishes. Admittedly, Luyendyk's strength on ovals did extend beyond Indianapolis with wins at Phoenix and Nazareth and arguably even more impressively a 2nd place finish at Michigan in 1994 for the backmarker team Indy Regency Racing. On road courses, Luyendyk definitely had some good runs but rarely if ever fought for wins on them, and it isn't a good sign when his most famous road course moment is probably the 1990 street race at the Meadowlands where he missed a corner, drove off the track and into a parking lot, but somehow finished 3rd. To be fair, the teams he was with were generally not great. Bettenhausen Racing never won a race, Hemelgarn never won until Buddy Lazier in the IRL years, Dick Simon Racing never won a race, he did better than Boesel but worse than Al Unser, Jr. at Doug Shierson Racing (which became Vince Granatelli Racing), and he was more successful in his one year with Ganassi in 1993 (before they became a powerhouse) than any of Ganassi's other drivers from 1990-1995 except Michael Andretti. After that, he was stuck in unreliable equipment until the formation of the IRL, where he would again not have the best equipment (which was Foyt and Menard), as his team Treadway Racing won only one race without him. He definitely had some career misfortune with both his teams in his best two seasons (1990 and 1991) shutting down at the end of the season and he raced during a very top-heavy period with six or seven major stars who commanded the premier teams preventing him from ever really getting a shot, but I don't think he was as good an example of overachieving in weak equipment over the entire schedule as Justin Wilson or Mike Mosley were. I don't really rate the IRL results very highly because he was practically the only driver with good recent experience in the early IRL seasons, the Indy 500 average speed record he set in 1990 doesn't mean much to me since all that means is the race didn't have many cautions, and his all-time record qualifying speed in 1996 means a little more but still not much since the boost was raised specifically to set records for that one year before switching to the IRL naturally-aspirated engines. I definitely find him overrated outside his Indianapolis performance, but out of respect to him struggling for many years with questionable teams before winning his 1990 Indy 500 for the good, not great Shierson team, the number of wins he had not in the best cars, the diversity he had across different kinds of ovals (even if he was average on road courses), and his ability to win with different kinds of equipment (the high-tech CART turbocharged engines and the low-tech IRL natural-aspirated engines) over a fairly extended period are still enough for him to deserve placement on the list. I wasn't really going to leave a two-time Indy 500 winner off of this list but I don't really see him as a lock either.
The Pikes Peak International Hill Climb is one of the most legendary races in the United States and is the second oldest race still annually being held, having started in 1916. From 1947-55 and 1965-69 the Hill Climb was included as a round of the AAA/USAC Champ Car Championship, the only rally races to be a part of the championship since the point-to-point races of the pioneering years. Much like the period from 1950-1960 when the Indy 500 technically counted as a round of the World Drivers' Championship even though the F1 drivers seldom crossed over while it counted for points, Pikes Peak counted for points in those years but rarely if ever did any of the Pikes Peak drivers enter other championship races and rarely did any of the championship drivers compete there. This changed in the late '60s, when Bobby Unser and Al Unser, who got their first starts and wins at Pikes Peak, crossed over to run the entire schedule, and when series regular Mario Andretti did a one-off at Pikes Peak and won. The race was a very standalone event on the schedule when Rogers competed in it, but in the years it counted for points, no driver was more dominant than Rogers, who won four years consecutively from 1948-1951, the first four years the event counted for points. Although Bobby Unser eventually won the race more often than anyone else, a grand total of ten times (1956, 1958-63, 1966, 1968, and 1986) only two of his came in seasons that counted, so from an IndyCar perspective, Rogers was the face of Pikes Peak. Many fans argue rallying by its very nature is more difficult than circuit racing to begin with and his success in that realm may indicate a versatility that he could have used to apply to ovals or road courses (as the Unsers did), but we will never know, since he chose to specialize in the one form of racing, but he is hardly the only driver who primarily specialized in one track type on this list and I feel that although overlooked, the Pikes Peak event is an important element of IndyCar history and an important element of American racing history in general and a Pikes Peak-only specialist deserves a slot on the list, especially since it did count for points and I am considering pioneering drivers who competed in certain races that did not.
The Vanderbilt Cup is now largely forgotten except for those people who remember the split years when CART reintroduced it after a decades-long absence as a prize for the U.S. 500 winner to rival the Borg-Warner Trophy, and then awarded it instead to the champion after the U.S. 500 name was retired for the Michigan race after the 1999 season. Whether you thought it was a good idea for CART to resuscitate it for that idea or not, it was a worthy callback to an era when races other than Indy mattered, and arguably in the 1910s the Vanderbilt Cup mattered just as much as Indianapolis did. The races, which usually every few years between 1904 and 1916, were the biggest prize in American road racing in that era and drew major crossovers from European cars and drivers as well. Although only the final race of that era in 1916 actually counted towards a points championship, the races were still very big prizes and much longer in both distance and time than any of today's road races, generally lasting 300 miles and four hours. These were obviously in some respect much more grueling exercises than anything recent drivers face, and although the depth of competition in this era was fairly weak, the drivers who excelled in the more prestigious races like the Vanderbilt Cup deserve respect. I thought including two road racing specialists from this era was overkill, so I felt I had to choose between Robertson, who in 1908, became the first American driver to win the event in an American car, or Harry Grant, who won the next two years and became the first driver to win the event multiple times. I chose Robertson because he was much more dominant and a lot more consistent than Grant, although unfortunately any of his pre-1909 results are lost to history and he retired due to injury not much later in 1910. As a result, he only has five starts in this analysis (and his Vanderbilt Cup win is not considered), but he managed to win two of them, both of which came against modern-sized fields of 17 and 21 cars, in approximately 300 mile road course races, one of which lasted nearly four hours and the other nearly six! As a result of those two wins, Robertson won an artificial championship declared by Russ Catlin many decades after the fact, but as mentioned in my introduction, these races are no longer judged to count, but that doesn't mean Robertson doesn't deserve more respect as one of the premier stars of the pioneering era, even if he retired before the Indy 500 started and never started an oval race.