Matthew Rosenbaum is a Rochester lawyer who collects multi-partisan political buttons. He visits political conventions and his outstanding collection is respected throughout the country.
Harry Truman never thought much of Adlai Stevenson. The button shown here depicts a buttoned-up Harry Truman, showing support for Adlai Stevenson for President. In 1956, the ever-popular Dwight David “Ike” Eisenhower was up for re-election. Although Ike was popular for his role in WWII, he hadn’t been as exciting as a Chief Executive. Republicans had lost ground in the mid-term elections, and the President had suffered a heart attack in 1955. Adlai Stevenson, who had unsuccessfully run against Eisenhower in 1952, thought he had a real chance, the second time around. Truman thought otherwise.
The former President cast his lot with New York Governor W. Averell Harriman as his pick for the Democratic nomination. Truman was very vocal about his support for Harriman, calling Stevenson a “defeatist candidate.” Stevenson’s people were incensed, and the Democrats looked like they might further fracture their party.
Ultimately, Stevenson was able to successfully out-maneuver Harriman with some well-timed endorsements and by promising to put a Southerner on the ticket. Stevenson successfully obtained his re-nomination, out-dueling both Truman and Harriman and further marginalizing the former President from his party. In the end, Stevenson lost once more to Ike. It wasn’t even close. And Truman was able to say the four words he’d been dying to say since Stevenson’s second nomination: “I told you so!”
The 1988 Democratic presidential primary was one of the most chaotic and unpredictable in modern American political history. It was a wide-open contest that reflected a party in transition, struggling to find its identity in the post-Reagan era. No other Democratic primary race before or since has featured as many different primary winners as the 1988 race. What began with a clear front-runner ended in a political free-for-all that captured the volatility and drama of American electoral politics.
The presumptive favorite at the outset was Senator Gary Hart of Colorado. Hart had been the runner-up in the 1984 Democratic primaries, finishing second to former Vice President Walter Mondale. With his youthful energy, moderate appeal, and forward-looking message, Hart seemed to represent the next generation of Democratic leadership. By the time 1988 rolled around, he was widely expected to secure the nomination with relative ease.
The Hart Scandal
But Hart’s campaign was derailed before it even had a chance to build momentum. In the fall of 1987, news broke that Hart had been involved in an extramarital affair with a woman named Donna Rice. The scandal, made all the worse by Hart’s earlier dare to the press to “follow me around,” dominated headlines. A photo of Rice sitting on Hart’s lap aboard a yacht named “Monkey Business” became emblematic of the controversy. Initially denying the affair, Hart eventually bowed to the mounting pressure and suspended his campaign. Though he briefly re-entered the race in early 1988, the damage was irreparable. His fall from grace opened the door to a crowded and unpredictable field.
The Race Without a Clear Leader
With Hart out of the way, the Democratic nomination became a wide-open race. Five different candidates would go on to win individual primaries and caucuses, highlighting the party’s fractured nature. The major contenders included civil rights leader Jesse Jackson, who energized voters with a historic and passionate campaign; Senator Al Gore of Tennessee, a youthful centrist voice from the South; Representative Dick Gephardt of Missouri, who emphasized labor and economic issues; and Senator Paul Simon of Illinois, known for his bow tie and earnest demeanor (not to be confused with the famous singer-songwriter of the same name).
Dukakis Emerges from the Pack
Michael Dukakis. Wikimedia Public Domain
Ultimately, it was Massachusetts Governor Michael Dukakis who emerged as the nominee. Dukakis ran as a technocratic, no-nonsense manager, touting his record of economic success and governmental efficiency in Massachusetts. To bring regional and ideological stability to the ticket, Dukakis selected Texas Senator Lloyd Bentsen as his running mate. Bentsen, a seasoned lawmaker with deep Southern roots and conservative credibility, was seen as a strategic pick to appeal to moderate and swing voters in the South.
Following the Democratic National Convention, the Dukakis-Bentsen ticket surged in the polls. For a brief moment, they held a comfortable lead over the Republican ticket of Vice President George H. W. Bush and Indiana Senator Dan Quayle. But the momentum didn’t last.
From Momentum to Missteps
A series of campaign missteps and public perception issues quickly eroded Dukakis’s advantage. One of the most infamous moments came when Dukakis participated in a photo opportunity riding in a military tank—a move meant to counter criticisms that he was weak on defense. Instead, the image backfired. The oversized helmet and his awkward appearance became a punchline and political liability, reinforcing the narrative that Dukakis was ill-suited to lead on national security.
Another blow came during a televised presidential debate, when Dukakis was asked whether he would support the death penalty if his wife were raped and murdered. His answer, a calm and rational “no,” delivered without a hint of emotion, stunned viewers. It may have been intellectually consistent with his principles, but to many voters, it came off as robotic and unfeeling—an image that plagued the rest of his campaign.
Election Day Results: A Harsh Reality
Despite these setbacks, Dukakis did manage to carry ten states on Election Day—a more substantial showing than any Democrat since Jimmy Carter’s victory in 1976. However, it wasn’t enough. George H. W. Bush won in 40 states and secured both the Electoral College and the popular vote with ease.
A Candid Conversation with Michael Dukakis
The following year, I had the chance to meet Dukakis at a health care conference. He was remarkably gracious, thoughtful, and patient, taking nearly ten minutes to talk with me about his campaign and the lessons he had learned from it. He acknowledged his mistakes without defensiveness and spoke candidly about how he had moved on. What struck me most was his humility. He shared a quiet anecdote: on Inauguration Day in 1989, he didn’t attend the ceremony. Instead, he packed a sandwich from home, stayed in, and watched George H. W. Bush’s inauguration on television. Just a regular guy.
That small moment of introspection said a lot. In an era of political theater and spin, Dukakis reminded me that behind every campaign is a real person—flawed, human, and capable of grace even in defeat.
In 2008, John McCain finally got his wish to be the Republican nominee for President. His timing and selection of a vice presidential candidate were both horrible.
Since 2005, President George W. Bush’s popularity has plummeted, due in part to the perceived mismanagement of Hurricane Katrina relief, specifically to New Orleans, and to a looming financial crisis that would crater the stock market in September 2008. This, coupled with a new face of the Democratic party in Barack Obama, made McCain’s climb to the pinnacle of American government that much steeper.
McCain, a decorated war hero, chose little-known Alaska Governor Sarah Palin for vice president. Though attractive, she was a fresh face in national politics and the first female nominated for Vice President of the Republican Party. Governor Palin proved to be a marketing disaster. Her appearances on national TV programs did nothing to dispel the idea that she was inexperienced and could be a divisive voice. The media did nothing to point out her positive attributes, namely that conservative women (and men) liked her.
Ultimately, Obama and Biden were handily beaten by McCain and Palin.
The pin shown here is one of my favorites from 2008. It was made for the Republican National Convention in St. Paul, Minnesota. The slogan and visuals are great, but the campaign was not.
Presidential candidate button of Nelson Rockefeller
New York has had many famous governors, from DeWitt Clinton to Mario Cuomo. None, however, compares to Nelson Rockefeller, the political and business giant.
A Man of the People
Rockefeller was elected to four terms as Governor of New York, more than any other Governor in the Empire State. Although his family was considered the richest in the world then, he was friendly and approachable, and truly loved meeting with regular citizens and rank-and-file voters. He was known for appearing unannounced on the state senate and assembly floors to push for bills he felt were essential to New York voters. His “Hiya Fella!” signature greeting is still remembered by those who had the pleasure of meeting him.
One of my associates told me he was sitting in his car on Madison Ave., stuck in traffic, when he looked to his left. There was Nelson Rockefeller in his limo right next to him. Rockefeller gave him a friendly wave and he waved back.
Political Career
‘Rocky’ had grand ambitions beyond New York State. He attempted to run for President three times, but his timing was always off. Ultimately, he was chosen by President Gerald Ford and confirmed by the Senate to be Ford’s Vice President, a position he never really wanted. His left-leaning policies made him anathema to the Republican Party, and ultimately, he was jettisoned from the Ford ticket for the election and replaced by the more conservative Bob Dole.
I love this pin because of Lincoln’s shadow and the conveyed message. Rocky was a forward thinker who cared about society’s betterment. He was the last governor to maintain New York’s status as the Empire State. Ten New York Governors were nominated for US President, and four were elected to the highest office in the land. Regrettably, Nelson Rockefeller wasn’t one of them.
1968 was a turbulent and tragic year in the political arena. Iconic civil rights leader Martin Luther King, Jr. was murdered, and then barely two months later, the presumptive Democratic nominee, Robert Kennedy, was assassinated. We saw three political organizations clash, resulting in the last time a third party received electoral votes in a presidential election. We also witnessed a sitting president, Lyndon Johnson, decline to seek another term.
Portrait of Dr. Martin Luther King Jr. Wikipedia, Public Domain
The country was a mess. Anti-Vietnam protests were raging, and the South was enraged by the Civil Rights movement supported by LBJ, a southerner. By the time the Democrats organized for their convention in Chicago, the party’s southern wing bolted to form their own Party, the American Independent Party, as they defiantly opposed the Civil Rights Movement and the end of segregation.
Rioting occurred outside the convention hall while the nominee, Hubert Humphrey, accepted his party’s nomination.
And Then There Was Wallace
The southern Democrats of the American Independent Party chose Governor George Wallace of Alabama as their standard bearer. They considered Wallace a prominent force supporting their ideology, as Wallace was not subtle regarding his views about race. He was adamantly against racial integration, and during his gubernatorial speech in 1963, he declared, “segregation now, segregation tomorrow, and segregation forever.” Martin Luther King labeled him as the “perhaps most dangerous racist in America today“.
On May 15, 1972, Wallace was shot by Arthur Bremer in Laurel, Maryland. Bremer was a 21-year-old from Milwaukee, Wisconsin. He fired several shots at Wallace and struck him multiple times while he was campaigning for the presidential nomination. Wallace was permanently paralyzed from the waist down and spent the rest of his life in a wheelchair. Three bystanders were also wounded. Bremer was initially sentenced in August 1972 to 63 years in prison, but the sentence was reduced to 53 years after an appeal in September 1972. Bremer is currently out of prison but is under mandatory supervision until May 15, 2025.
Republician Comradery
The Republicans came together and nominated perennial candidate Richard Nixon. The liberals wanted Nelson Rockefeller of New York, and the Conservatives considered supporting Governor Ronald Reagan of California. In the end, Nixon was nominated and, with the Democrats split, he was elected in November. Wallace won five states over both major parties, helping to hamper Humphrey’s election chances. Nixon won a landslide in 1972, but then Watergate undid him. Humphrey never ran again.
The Civil Rights Riots
The “civil rights riots” of the 1960s refer to a series of significant outbreaks of civil unrest in urban areas, primarily driven by deep-seated racial injustice and frustrations among the black community. While the Civil Rights Movement is often associated with nonviolent protests, such as those by Martin Luther King, the riots represented another, more volatile, response to the slow pace of change faced by African Americans.
The most significant wave of these riots occurred during the “long, hot summers” of the mid-to-late 1960s, particularly from 1964 to 1969. People would watch these riots unfold on their black-and-white TVs in awe, anger, or support for their cause. They took place in major cities across the country, including:
Harlem, New York (1964) – Often seen as the start of this period of widespread unrest.
Watts, Los Angeles (1965) – One of the most destructive and well-known riots.
Chicago, Illinois (1966, 1968)
Cleveland, Ohio (1966)
Newark, New Jersey (1967)
Detroit, Michigan (1967) – Among the deadliest and most destructive.
Following the assassination of Martin Luther King Jr. (April 1968), a wave of riots erupted in over 100 cities nationwide.
Vietnam
If racial injustice and violent rioting weren’t enough to make your blood boil (for whatever reason), protests against the Vietnam War were another.
Young people, especially those of college age, who knew they would be drafted soon, started to protest the draft. There were a number of reasons that led up to this.
They didn’t understand why we were fighting a war six thousand miles away in order to accomplish something that they didn’t feel was necessary to put their lives on the line.
Television was still relatively new, and this was the first time the world, including the students, could see with their own eyes the bloodshed that took place in Indonesia.
The high number of civilian casualties turned public opinion sharply, and not just among students, which led to political divides in Congress and the Senate.
Not Everyone Was Protesting
Baby boomers were not happy with these protests. Many of them served in the military during WWII and found these student demonstrations a copout. People would periodically see on the news about construction workers in NYC and other cities taking offense at them, and on certain occasions, they would assault them.
By 1969, the country had had enough, and President Nixon began withdrawing our troops from the war-torn, bloody country. The final contingent of US troops came back on March 29, 1973.
As 1968 was the most tumultuous year of the decade, it is hard to believe that the following year brought the “Summer of Love.”
Thomas Dewey, the Republican governor of New York, is most famously remembered for his 1948 presidential election loss to Harry S. Truman, cemented in the iconic “Dewey Defeats Truman” headline. However, Dewey’s political career and influence extended far beyond this moment.
Dewey was a prominent figure in the Republican Party, known for his reputation as a “gangbuster” prosecutor in New York City during the 1930s. His intense focus on organized crime concerned the New York mobsters of that era, and discussions ensued about what to do about it.
One gangster, Dutch Schultz, took Dewey’s organized crime attacks so seriously that he became adamant about eliminating him. The recently created ‘committee’ voted against it, fearing law enforcement would target them, but Schultz stood steadfast with his assassination decree. He stormed out of the room, saying he would take care of it himself. This led to Shultz’s assassination by the syndicate.
Political Cartoonist Clifford K. Berryman‘s editorial illustration of October 19, 1948, shows the consensus of experts in mid-October. National Archives and Records Administration, cataloged under the National Archives Identifier (NAID) 306150—Public Domain.
Dewey was propelled into the governorship of New York, where he established a record of efficient and progressive administration. In 1944, Dewey received the Republican presidential nomination, challenging Franklin D. Roosevelt during World War II. Though he lost the election, his strong showing solidified his position as a leading Republican figure.
Thomas E. Dewey was a two-time Republican presidential nominee who played a significant role in mid-20th-century American politics. As the Governor of New York and a tough-on-crime prosecutor, Dewey was widely respected within the Party. He ran again in 1948 against Harry Truman, with his second campaign being one of the most famous upsets in U.S. history. Although he never won the presidency, his influence shaped the Republican Party for years.
Another important historical figure from our past that most people don’t know is Charles Evans Hughes. Charles Evans Hughes was a former popular Governor of New York. He was a brilliant legal mind and was nominated to serve on the US Supreme Court in 1910 by President William Howard Taft. Justice Hughes sat on the US Supreme Court as an Associate Justice for barely six years before he agreed to be the Republican Party’s standard bearer for the 1916 Presidential election.
The world was at war, and many did not think the current President, Woodrow Wilson, would prevent the US from entering the conflict. Hughes became the favorite, and on the day after the election, several prominent newspapers declared him the victor.
In actuality, Wilson won a second term in a very tight race. Hughes had lost his Supreme Court job, which he dearly loved, and then lost his shot at the Presidency, a job he truly desired. He wound up serving as Secretary of State in the 1920s, but then President Hoover nominated him to sit on the Supreme Court again, this time as Chief Justice. Hughes served as the 11th Chief Justice of the United States Supreme Court from 1930 to 1941. I always find it fascinating that most people don’t know who he was, but he served as an important historical figure for nearly four decades.
The Kennedy family is one of American history’s most influential and well-known political dynasties. Their legacy spans politics, public service, business, and popular culture. The family’s prominence began with Joseph P. Kennedy Sr., a wealthy businessman and U.S. ambassador to the United Kingdom, who had ambitious plans for his children to enter politics. There was a dark past regarding Joe Kennedy’s legacy, where he has been known to work with organized crime during the probation period.
Joe’s sons—John F. Kennedy (JFK), Robert F. Kennedy (RFK), and Edward “Ted” Kennedy—would go on to shape American history significantly.
John F. Kennedy (1917–1963)
JFK was elected the 35th president of the United States in 1960, becoming the youngest person ever elected to the office. His presidency was marked by major events such as the Cuban Missile Crisis, the advancement of the Civil Rights Movement, and the Space Race, during which he set the goal of landing a man on the moon.
Robert F. Kennedy (1925–1968)
Political button of Robert F. Kennedy
RFK, JFK’s younger brother, served as U.S. Attorney General and later became a U.S. senator from New York. He played a key role in the civil rights movement and was a strong advocate for social justice. In 1968, he ran for president, but his campaign was cut short when he was assassinated in Los Angeles after winning the California primary.
Ted Kennedy (1932–2009)
Ted Kennedy, the youngest Kennedy brother, served in the U.S. Senate for nearly 47 years, making him one of the longest-serving senators in U.S. history. Despite controversies, including the Chappaquiddick incident, he became a champion for health care, workers’ rights, and education reform.
The Kennedy Legacy
The Kennedy family’s influence continues into modern times, with members like Caroline Kennedy and Robert F. Kennedy Jr. playing roles in politics and activism. Despite tragedies, including JFK Jr.’s plane crash in 1999, the family’s name remains synonymous with political ambition, public service, and the idea of “Camelot”—a romanticized era of American optimism.
The Kennedys’ story is one of triumph and tragedy, filled with political achievements, personal losses, and an enduring legacy that continues to fascinate the world.
The Presidency
Believe it or not, when John Kennedy and Lyndon Johnson ran in 1960, they were the first top-ticket candidates born in the 20th century. Up until then, much older men had mostly occupied the White House. Kennedy barely bested Richard Nixon in 1960, and great hopes were pinned on the young man and his family.
As many know, Kennedy never served out his first term, having been assassinated in November of 1963. But during his term, two other Kennedys came on the scene. Kennedy picked his younger brother Bobby as his US Attorney General.
His youngest brother, Teddy, would run for Senate in Massachusetts in 1962, using most of Kennedy’s marketing materials for continuity. Note the nearly identical pins below of JFK and Teddy. RFK ran for NY US Senate in 1964, won, and became the Democrat Presidential favorite in 1968 after LBJ dropped out. RFK, too, would be felled by an assassin’s bullet immediately following his big win in the California primary in June. Only Teddy survived throughout the decades into the 21st Century. Many Democrats lionized the Kennedys, but the family mainly knew nothing but tragedy after tragedy.
One of the more humorous buttons I have owned is an anti-Dan Quayle button from 1990. In 1988, Vice President George HW Bush plucked a young Indiana Senator from obscurity and made Dan Quayle his running mate.
Senator Quayle was young and attractive but incredibly inarticulate. He was so gaffe-prone that many thought Bush would remove him from the ticket when he ran for re-election. Some people were seriously concerned that Bush might somehow die in office and the most essential job in the world would fall into Dan Quayle’s lap; thus, the button shown here.
One incident that led to Quayl’s gaff popularity was the “potatoe” incident. happened on June 15, 1992, when he was Vice President of the United States.
While visiting Munoz Rivera Elementary School in Trenton, New Jersey, Quayle participated in a spelling bee with a group of students. A 12-year-old student, William Figueroa, correctly spelled the word “potato” on the chalkboard. However, Quayle, reading from a flashcard with a spelling mistake, mistakenly corrected the student by adding an extra “e,” making it “potatoe.”
This minor mistake quickly became a national joke and reinforced a public perception of Quayle as error-prone. The incident was widely mocked in the media, on late-night TV, and in political satire, despite Quayle later explaining that he was simply following the incorrect cue card provided by the school. The blunder haunted Quayle throughout his political career and remains one of U.S. history’s most famous political gaffes.
Ultimately, Bush and Quayle would stick together and were defeated by a young regional ticket of Bill Clinton and Al Gore in 1992.
I had the pleasure of meeting Dan Quayle in 1991 and was amazed to learn how knowledgeable he was about world affairs and how he didn’t stumble over his words at all during a one-on-one conversation. He was genuinely nice and engaging, and I felt bad that the press had treated him so poorly. He will always be known as a Vice President who appeared out of his depth.
The 1976 Republican Convention was the last time there was an actual floor fight for the nomination of a major Party President. It was a hotly contested battle between incumbent President Ford and challenger Ronald Reagan.
The Republicans, fractured from Watergate, met in Kansas City to nominate their candidate to run against Jimmy Carter. President Gerald Ford had been damaged by pardoning former President Richard Nixon. Conservative Republicans smelled blood in the water, and it didn’t help that Ford had initially picked Nelson Rockefeller, an Eastern Establishment Liberal, as his choice for running mate. Their preferred candidate, former Governor Ronald Reagan, took on Ford and won 24 of 50 contests. The party was nearly split down the middle when they made it to the convention.
There were a small number of undecided delegates, but most were persuaded by the NYS Republican Chairman (my father), Dick Rosenbaum, to side with Ford. After the balloting, Ford won the majority by less than 100 votes. Ford was compromised and ultimately jettisoned Rocky for Kansas Senator Bob Dole to appease the Conservatives. By Election Day, they had nearly clawed their way back but ultimately came up short in a squeaker of an election.
About the Pin
The pin featured is one of my favorites. It displays the animus between the two Republican candidates. Two different pins were made—one featuring one candidate in a White cowboy hat (the “good guy”) and one featuring the other candidate in a black hat (the “bad guy”). The pin highlighted here is slightly rarer in that Ford was the incumbent and generally was seen with the white hat.
State Chair Dick Rosenbaum
Below there are two videos that feature State Chair and Ford loyalist Dick Rosenbaum. In the first one, he describes his altercation with a Reagan delegate. You don’t see him decking the delegate and dragging him off the convention floor. The second is his nomination of the President, which ultimately gave Ford the majority.
Dick Rosenbaum was a key political figure and staunch supporter of Gerald Ford during the 1976 Republican National Convention. The two videos here highlight pivotal moments in Rosenbaum’s role at the convention.
Video 1: The Altercation with a Reagan Delegate
In the first video, Rosenbaum recounts a physical confrontation with a Reagan delegate on the convention floor. While the video does not explicitly show Rosenbaum striking the delegates or physically removing them, his account suggests a heated and possibly aggressive exchange during a critical convention moment. Such tensions were common, as the Ford and Reagan camps were fiercely competing for delegate support in what became one of the closest nomination fights in modern Republican history.
Video 2: The Nomination of President Ford
The second video features Rosenbaum officially nominating President Gerald Ford, a significant moment that helped Ford secure the majority needed to win the Republican nomination. Rosenbaum’s nomination speech and actions were crucial in ensuring Ford’s victory over Reagan at the convention. Although Reagan had strong grassroots support, Ford ultimately edged him out in the delegate count, primarily due to loyalists like Rosenbaum working behind the scenes to rally votes.
This account underscores the intense political infighting at the 1976 Republican National Convention, a moment that shaped the GOP’s future and influenced Reagan’s eventual rise to the presidency in 1980.
