As someone with a dog in the current Presidential fight, there’s a part of me (actually, all of me) that boggles at the idea this is even a competition. That we’re really trying to decide between the two nominees, since one is clearly more qualified than the other. Then again, I always knew that Hillary Clinton’s qualifications for the office were never going to be a major selling point. After all, this is America. Being qualified for a job, particularly if you’re a woman, is beside the point.

In fact, if Clinton loses, she joins a rather long parade of people who had all of the qualifications to be President, but never got over the hump to actually getting elected. So I’ve decided to take a look at some of these folks, forming a list that I call: The Should’ve Beens.

A couple rules regarding this list:

1. It’s not open to people who have been considered Presidential possibilities, but never got their party’s nomination (Robert Taft, Robert LaFollette, Ted Kennedy). You have to have made the final round.

2. Perhaps more importantly, this IS NOT an attempt to rewrite U.S. electoral history. DO NOT take the placement of some people on this list to mean “So-and-so should have been elected over such-and-such this particular year.” Sometimes perfectly good candidates wind up running against other perfectly good candidates and get defeated. That’s politics. The guys (and sadly, it is all guys) on this list are people who by dint of their experience, knowledge and stature really should have been President at SOME point. Clear enough?

Okay, here’s what I got:

1. Al Gore

RESUME: U.S. Representative from Tennessee, U.S. Senator from Tennessee, two-term Vice President of the United States.

THE BONA FIDES: During his time in Congress and later as the Vice President, Gore was a cutting-edge advocate of two issues that would become Democratic centerpieces: the fight against global warming and the integration of technology into U.S. manufacturing. Gore’s advocacy of the latter played a key role in the “dot-com” boom which helped fuel the Clinton economic expansion of the 90’s. At the time of his selection as Clinton’s running mate, Gore was called “the best V.P. pick in at least 20 years.” (Of course, 20 years from 1992 would have been 1972, in which George McGovern had to dump his original pick Thomas Eagleton and then was turned down by every Democrat including the ghost of Woodrow Wilson before replacing Eagleton with Sargent Shriver. And the other party had Spiro Agnew, so…) As VP, Gore continued the evolution of the office into that of the President’s top adviser.

WHAT WENT WRONG: This is going to be a common theme on this list, but Gore’s main difficulty was an inability to connect with the voting public. While he was respected, his persona most closely resembled that kid at the high school lunch table who bores you with the finer points of computers or Dungeons and Dragons and when he realizes you’re not following, gives you this pitying, disgusted look that makes you feel bad for a second before you realize, “Wait a minute, I’M not the one who should feel embarrassed!” Additionally, Gore’s signature accomplishments (global warming and technology) failed to move the public. Global warming is STILL, for reasons passing understanding, a subject for debate. Gore’s advocacy of expanding the military’s ARPANET system into what we now call the internet somehow became the utterly false claim that “Al Gore says he invented the internet.” Also, Gore’s moderate stances from early in his career came back to haunt him. He opposed gay rights and abortion funding and his wife Tipper started the PMRC, whose drive to put warning labels on potentially offensive CDs smacked of censorship. While Gore shifted some of these views over time, he was never entirely trusted by liberals, something that cost him dearly in the 2000 election.

2. Hubert Humphrey

RESUME: U.S. Senator from Minnesota, Vice-President of the United States

THE BONA FIDES: As mayor of Minneapolis, Humphrey ran on an anti-corruption ticket and gained notoriety for cleaning up the city’s criminal element. He formed the Americans for Democratic Action to fight communist influences in his party and was one of the architects of the merger between the Democratic and Farmer-Laborer parties, strengthening Minnesota’s left wing. At the 1948 Democratic National Convention, Humphrey delivered a rousing speech in favor of adding a strong civil rights plank into the party platform. The move completed the party’s shift away from state’s rights and did much to make the Democratic Party viable in the African-American community. During his first tenure in the Senate, Humphrey advocated arms control, nuclear test ban treaties and humanitarian foreign aid. He co-sponsored legislation that eventually created the Peace Corps. He rose to the position of Majority Whip and played a major role in the passage of the Civil Rights Act of 1964. Humphrey’s mentor, Lyndon Johnson, selected him as his running mate, elevating Humphrey to the Vice Presidency. In that role, Humphrey tried to dissuade LBJ from bombing North Vietnam, pointing out correctly that it would lead to the U.S. committing ground forces and extending the conflict.

WHAT WENT WRONG: Unlike most others on this list, charisma was never Humphrey’s problem. He was an accomplished and witty speaker. His outgoing personality and forceful advocacy of social causes earned him the nickname, “The Happy Warrior”. In 1968, he fought back from an early deficit in the polls and nearly defeated Richard Nixon. Ultimately, Humphrey’s undoing was his support of the Johnson administration’s actions in Vietnam. Johnson flatly told Humphrey to get on board or he’d make sure Humphrey would never get the Democratic nomination. Though personally opposed to Vietnam, Humphrey would be tainted with the unpopularity of the war, particularly among his liberal base. He would come to rue his toeing the administration’s line, saying, “I ought not to have let a man (Johnson) who was going to be a former President dictate my future.” Timing also didn’t work in Humphrey’s favor. His 1960 Presidential campaign was steamrolled by the well-funded Kennedy machine and in 1972, the party embraced George McGovern rather than a once-defeated candidate in Humphrey.

3. Thomas Dewey

RESUME: New York District Attorney, Governor of New York

THE BONA FIDES: Dewey sprang to the public’s attention for his work prosecuting organized crime, first as a federal special prosecutor and later as New York District Attorney. In that capacity, Dewey put away the likes of Lucky Luciano, Dutch Schultz and Louis Lepke and, if mob lore is to be believed, was lucky to have survived. He would go on to serve three terms as governor of New York. By any yardstick, Dewey was spectacularly successful. He doubled state aid to education, increased salaries for state employees, signed legislation that created the State University of New York and the New York State Thruway, created a state Department of Commerce, added 14,000 beds in the state’s mental health system, provided public housing for 30,000 families, allowed for the reforestation of 34 million trees, created a water pollution program, provided slum clearance, provided pay for a model veteran’s program and signed the first state law in the country that prohibited racial discrimination. Oh, and he did all this while creating a budget SURPLUS of over 600 million dollars. In Dewey’s own words, “Government can be progressive and solvent at the same time.”

WHAT WENT WRONG: It was said of Republican President Benjamin Harrison that, while a magnificent orator, he should never be allowed to meet the public. Harrison was so famously repellent in manner that everyone who shook his hand, it was said, walked away a Democrat. Perhaps if Dewey had lived in Harrison’s time, he would have, like Harrison, gotten at least one shot at the Presidency. But Dewey lived in a time in which mass media was beginning to influence public opinion. Dewey came off as cocky, unemotional and suspicious. He tended to brook no opposition from New York state legislators, often ordering them to be investigated if they opposed his legislation. Timing certainly didn’t help his first nomination as President in 1944. World War II was not only at its height, but going well for the Allies. No one was in the mood to change horses, so Dewey had no real chance against Franklin Roosevelt. In 1948, though, Dewey let a golden opportunity slip through his fingers. President Harry Truman was at the nadir of his popularity, largely for the unforgivable crime of not being FDR. Dewey had a huge lead in the polls and was considered a virtual certainty to win. But the lead made him overly-cautious and caused Dewey to run one of the least inspiring campaigns in history, highlighted by such bold statements as, “Your future is in front of you.” Truman, meanwhile, barnstormed the country and effectively used the equally-unpopular Republican-controlled Congress as a bludgeon against Dewey. In terms of public image, Truman had “Give ’em hell, Harry” while Dewey had Alice Roosevelt comparing him to the little man on the wedding cake. The result was Truman pulling off the come-from-behind victory while Dewey, via the infamous DEWEY DEFEATS TRUMAN headline in the Chicago Daily Tribune, became the best-known Presidential loser in history. While he never ran for President again, Dewey was hugely influential in getting Dwight Eisenhower the Republican nomination in 1952. Perhaps Dewey realized that while he and Eisenhower were identical in ideology, Ike could command the love of the public in a way Dewey never could.

4. Charles Evans Hughes

RESUME: Governor of New York, Associate Justice in the United States Supreme Court, Secretary of State, Chief Justice of the United States Supreme Court.

THE BONA FIDES: I’ll be honest: of all the people on this list, Hughes is the one that most makes me say, “How? How did this guy never get to be President?” I mean, do I even need to go into the Bona Fides? Look at his damn resume! Hughes was a fairly rare creature: a conservative who could embrace progressive legislation if he felt it was in the public’s best interest. As Governor of New York, he secured the passage of campaign finance reform laws that limited the power of corporations and political machines to influence state legislators. He extended gubernatorial oversight of state agencies and contractors, which limited corruption in state government. He signed legislation limiting child labor and reducing the lengths of the work day for factory workers. As Secretary of State, he brokered agreements among the major powers to limit naval expansion and he ended the U.S.’s six year occupation of the Dominican Republic. As Chief Justice of the Supreme Court, he ruled on New Deal legislation, upholding Social Security, child welfare, minimum wage and the right to collective bargaining, while also rejecting legislation that he felt was poorly written, nonspecific or redundant. Hughes was often the fulcrum between liberal and conservative justices and exerted such enormous influence that he is considered one of the great Chief Justices in American history.

WHAT WENT WRONG: While Hughes was widely respected that often doesn’t translate into being well-liked. Publicly, Hughes was considered aloof and a tad prissy (he acquired the nickname Charles The Baptist for his pious ways. Theodore Roosevelt, who loved emasculating those he opposed, privately referred to Hughes as The Bearded Lady.) Timing certainly didn’t help him. He was mentioned as a Presidential possibility in 1908, at the height of his popularity as Governor of New York, but had the misfortune of not being Roosevelt’s handpicked successor. When Hughes was nominated in 1916, with World War I raging, his party was split between pro- and anti-war factions. Hughes, not wanting to alienate voters, didn’t chose either side. The result was that he did not present a strong opposition to President Woodrow Wilson, as he had no new policies to offer and no Presidential record to run on. It’s a testament to Wilson’s unpopularity that the results were as close as they were. After that defeat, there were a few “booms” for Hughes in subsequent election years, particularly 1928, but Hughes declined to run. Truthfully: our loss.

5. James G. Blaine

RESUME: U.S. Representative from Maine, Speaker of the House, Senator from Maine, two-time Secretary of State.

THE BONA FIDES: Blaine seems rather lost to history, but he was a towering figure in the Republican party in the later 1800’s; arguably the most influential Republican between Lincoln and Theodore Roosevelt. A charismatic leader and a magnificent speaker, Blaine captured the public’s imagination in a way that very few Republicans (some of whom would wind up in the White House) ever could. As first a U.S. Representative from Maine and later as Speaker of the House, Blaine was seen as a common sense, moderate Republican; staunchly supportive of Union efforts in the Civil War, but not so punitive in his treatment of former Confederates afterwards. His reputation for honesty put him in contrast with the scandal-ridden Ulysses S. Grant administration. While Blaine didn’t take the same leadership role in the Senate, he was a prominent figure, serving on the Appropriations Committee and the Committee on Civil Service. Blaine would twice serve as Secretary of State, first under James Garfield and again for Benjamin Harrison. Blaine rejected the country’s long-held belief in isolationism and advocated America taking a role on the world stage. He strengthened ties with Latin America, calling for a conference that eventually led to the creation of the Organization of American States and pushing tariff reciprocity that boosted trade. He established a relationship with the new government of Hawaii, one that would eventually lead to the annexation of the islands. It has been said, with some justification, that Blaine’s foreign policy was the most distinguished and perhaps ONLY distinguished part of Harrison’s administration.

WHAT WENT WRONG: At first glance, Blaine’s failure to capture the Presidency is kind of baffling. In the second half of the 19th Century, a prominent Republican really just needed to express interest in the Presidency in order to get the job. But Blaine was undone by a combination of both sinning and being sinned against. In the former area, Blaine’s reputation for honesty was severely damaged in 1876 by allegations that he had accepted a huge cash payment from Union Pacific Railroad in exchange for bonds that were nearly worthless. While nothing was ever proven and no action ever taken against Blaine, he was unable to satisfactorily explain the payments and the entire scandal followed him through his career like a bad smell. Blaine was also a victim of circumstance. While the scandal wasn’t a deathblow in and of itself, it put Blaine in some unsavory company. For as successful as Republicans were in winning the Presidency, they didn’t have a particularly good reputation for governance. Andrew Johnson had been impeached. Grant’s administration was awash in scandal. Rutherford B. Hayes was seen as honest, but the circumstances of his election reeked of corruption. Garfield’s assassination was seen as the inevitable result of Republican “spoilsmanship”. Chester A. Arthur was also seen as honest, but tainted by his affiliation with the corrupt New York political machine. By the time Blaine got the nomination in 1884, he was viewed as just another suspect Republican trying to get the highest office in the land. Even members of his own party deserted him, seeing Blaine’s nomination as the death of the Republican party (God, I wonder what these folks would have thought of Trump?) How bad was it for Blaine? His opponent, Grover Cleveland, admitted to fathering a child out of wedlock. Yeah, a sex scandal. In 1884. The modern equivalent would involve cheating on your spouse while committing a terrorist attack and then posting the whole thing to You Tube. And Blaine STILL lost. Blaine might have had another shot at the Presidency in 1888 and 1892, but by then his health was failing. In fact, had he won the 1892 election, he wouldn’t have survived to his own inauguration, passing away in January, 1893. Clearly, it just wasn’t meant to be.

6. HENRY CLAY

RESUME: U.S. Senator from Kentucky, U.S. Representative from Kentucky, Speaker of the House, Secretary of State

THE BONA FIDES: If the U.S. didn’t plunge into civil war long before it actually did, it had Henry Clay to thank. Clay played major roles in the Missouri Compromise of 1820 (guaranteeing the entry of both Maine and Missouri into the union and banning slavery in new northern territories), the Compromise Tariff of 1833 (essentially keeping South Carolina from seceding…although part of that may have been the lack of anyone in South Carolina with the guts to walk up to Andrew Jackson and tell him they were seceding) and the Compromise of 1850 (a series of agreements that allowed California to become a state, banned slavery in the District Columbia and declared that Congress had no power to restrict the inter-state slave trade.) Clay was elected Speaker on his first day in the House, something that hadn’t happened before and hasn’t happened since. Clay transformed the office of Speaker by using it to appoint the chairs of all committees, creating a role that was only second to the President in terms of power. That influence continues to this day. Clay had a hand in creating the African nation of Liberia as a refuge for freed slaves (even if his motives of racial exclusivity were less than noble.) He helped negotiate the Treaty of Ghent that ended the War of 1812. As Secretary of State, he recognized and protected Latin American republics that broke away from Spanish or Portuguese rule. Clay advocated the American System, a plan to expand American infrastructure, banking and manufacturing, both as a means of making internal improvements and breaking down sectional differences. He was a founder of the Whig Party, which provided opposition to the dominant Democratic Party for more than 25 years. He was twice their nominee for President.

WHAT WENT WRONG: (Despite what you may be thinking, personal appearance had nothing do with it. Yes, based on the picture above, the man looked Neil Young after he’d been hiding in your closet for three days. But in the first half of the 19th Century, that was not considered a deal-breaker.)

If Clay never achieved the Presidency, it certainly wasn’t for a lack of trying. He was one of four Democratic-Republicans running for President in 1824. With none of the candidates achieving an Electoral College majority, the election was thrown to the House, where Clay used his influence as Speaker to swing the election for John Quincy Adams. When Clay was appointed Adams’ Secretary of State, supporters of Andrew Jackson called it a “corrupt bargain”. The charge, of course, was ridiculous (so Clay and Adams invented the notion of “I’ll scratch my back if you scratch mine”?) but it still tarnished Clay’s reputation and may have permanently damaged his Presidential prospects. Outside of Kentucky, Clay had no natural constituency. His advocating a national infrastructure ran counter to Southern sensibilities and as a slaveholder from a border state, Clay was not embraced by Northerners. It’s hard to be President when you’re essentially a man without a country. The only two times the Whigs successfully elected a President, it was because the country chose a political outsider and rejected someone who was seen as a career politician.

Here’s to hoping history doesn’t repeat itself.

HONORABLE MENTION: Mitt Romney (Don’t look at me like. Dude seems like William The Conqueror right about now, doesn’t he?), Bob Dole (“Nobody needs to tell Bob Dole that Bob Dole belongs on this list.”), Samuel Tilden (Just take my word on this), Stephen A. Douglas (How close was he? He was in the original draft of this article) and Lewis Cass (Nothing to say here, but Cass Lake is named after him and it’s, it’s nice.)