Pick up any Federal Reserve Note from your wallet and you are holding the end result of a surprisingly contentious bureaucratic and political process. The face staring back at you was chosen not purely on historical merit, not simply because an artist found the likeness compelling, and certainly not through any democratic vote. Portrait selection for United States currency has always been a negotiation among Treasury secretaries, Congressional allies, Bureau of Engraving and Printing craftsmen, and occasionally sitting presidents with strong opinions about whose face deserved the honor. The story of how those choices were made is one of the most underappreciated chapters in American numismatic history.
The Early Years: Chase, Lincoln, and the Problem of Self-Promotion
The first significant controversy in US currency portraiture occurred almost immediately after the government began printing paper money in earnest. Secretary of the Treasury Salmon P. Chase, who oversaw the creation of the first Demand Notes in 1861 and the Legal Tender Notes beginning in 1862, placed his own portrait on the $1 Legal Tender Note of 1862 and 1863. Chase was not shy about the self-promotion. He was an ambitious politician with presidential aspirations, and currency was one of the most widely circulated media in the country. Every farmer, merchant, and soldier who handled a dollar bill would see his face.
President Lincoln tolerated this, reportedly remarking with characteristic dry wit that it was a pity Chase had not put his face on a larger denomination. When Chase briefly resigned and was later appointed Chief Justice of the Supreme Court in 1864, his portrait migrated across several note types. Collectors today specifically seek the Fr. 16 and Fr. 17 varieties of the 1862 $1 Legal Tender Notes, which carry the Chase portrait. In Fine condition these catalog at roughly $400 to $600, while examples in Very Fine grade can reach $1,200 or more depending on the signature combination.
The backlash against Chase’s self-portrait gambit contributed directly to the 1866 law prohibiting portraits of living persons on US currency and government securities. It was one of the earliest examples of Congress legislating portrait aesthetics, and it set a precedent that still governs the process today.
The 1862 and 1863 Legal Tender Notes featuring Salmon Chase are far more historically significant than their catalog values alone suggest. Look specifically for the Chittenden-Spinner and Colby-Spinner signature combinations on Fr. 16 through Fr. 18. These are genuinely scarce in grades above Very Fine and represent a unique moment when a sitting Cabinet member literally put his own face on the money supply.
The 1869 Rainbow Notes: Aesthetic Ambition Meets Political Reality
The Series of 1869 Legal Tender Notes, nicknamed the Rainbow Notes for their vivid multicolor designs, represent the BEP’s most ambitious early attempt to assign portraits with deliberate symbolic weight. The designers, working under Engraver-in-Chief James P. Major, matched denominations to portraits in a way meant to signal value hierarchies. Columbus appeared on the $1, Jefferson on the $2, Lincoln on the $5, Hamilton on the $10, Daniel Webster on the $50, and Henry Clay on the $100. The $500 featured General Joseph Mansfield, and the $1,000 carried a portrait of DeWitt Clinton.
The choices reveal a specific ideological moment. Webster and Clay, both deceased giants of the antebellum Senate, were placed on high denominations as symbols of national unity. Their presence was partly a gesture toward reconciliation in the aftermath of the Civil War. Lincoln, still raw in public memory just four years after his assassination, was given the $5, a denomination that would handle enormous daily transaction volume, essentially making him omnipresent in commerce.
The $1,000 DeWitt Clinton is among the most coveted notes of the entire Legal Tender series. Fr. 187a, the 1869 issue with Allison-Spinner signatures, survives in an estimated population of fewer than 20 examples across all grades. A VF example sold at Heritage Auctions in 2014 for $176,250, a figure that underscores how portrait assignment to high denominations translated directly into modern rarity and value.
Treasury Secretaries as Curators: The Power Behind the Faces
Between the 1870s and the watershed redesign of 1928, Treasury secretaries exercised enormous personal discretion over portraiture. This led to some genuinely odd choices driven more by personal loyalty or political calculation than historical significance. Secretary John Sherman, serving under President Hayes, pushed for William Meredith to appear on the $2 note in the 1878 series, a choice that struck many contemporaries as obscure. Meredith had served as Treasury Secretary from 1849 to 1850 and had few other claims to historical prominence.
The Silver Certificate series of the 1880s and 1890s produced some of the most visually diverse portraiture in American currency history precisely because each new Treasury Secretary felt empowered to make changes. The $1 Silver Certificate ran through portraits of Martha Washington (1886, 1891 series), a design choice that was itself politically loaded, as advocates for women’s suffrage championed her inclusion while critics argued that currency should feature statesmen rather than their spouses. The Fr. 222 through Fr. 226 range covering the 1886 Martha Washington $1 Silver Certificates are perennial favorites with collectors. A Fr. 223 in Extremely Fine recently cataloged at around $475 in the PCGS Price Guide.
Martha Washington Silver Certificates from the 1886 series (Fr. 215 through Fr. 221 for the $2, and Fr. 222 through Fr. 226 for the $1) are among the few US notes to feature a woman’s portrait. Population reports from PCGS and PMG show that high-grade examples in gem uncirculated condition are genuinely scarce. If you find raw examples at paper money shows, they are worth submitting for grading since even modest upgrades from VF to EF can triple the realized value.
The Great Standardization of 1928
The shift from large-size to small-size currency in 1928 forced the most comprehensive portrait review in American history. The Treasury Department under Secretary Andrew Mellon, working with BEP Director Alvin Hall, had to assign stable, lasting portraits to just seven circulating denominations. The decisions made in 1927 and early 1928 have governed our pocket money ever since, which makes understanding their logic critically important for collectors.
Mellon’s committee applied what it described as a hierarchy of national service. Presidents dominated the lower denominations, which saw daily mass circulation. Washington went to the $1, Jefferson to the $2, Lincoln to the $5, and Jackson to the $20. Hamilton ($10) and Grant ($50) were non-presidential statesmen and military figures placed on denominations with moderate transaction frequency. Franklin ($100) was chosen as the century note’s face because he was viewed as the quintessential self-made American and carried enormous international name recognition, an important consideration given the dollar’s growing role in global trade.
The committee specifically debated whether Grant or Sherman should take the $50. Grant won partly because of his presidential status and partly because Sherman’s association with the controversial March to the Sea remained a raw nerve in Southern political circles. Currency had to be accepted everywhere, and a portrait that alienated a large regional population was a practical liability.
The resulting 1928 series is a cornerstone of any serious small-size collection. The Series 1928 $2 Federal Reserve Note (Friedberg 1551 through 1551H by district) is particularly interesting because within two decades the $2 denomination would become erratic in its production, making early 1928 examples in uncirculated condition meaningful keys. Star notes from the 1928 $2 FRN series in high grade can fetch $800 to over $2,000 depending on the issuing district.
The High-Denomination Portraits and Their Vanishing Acts
The portraits assigned to the $500, $1,000, $5,000, and $10,000 denominations in 1928 tell their own story. McKinley ($500), Cleveland ($1,000), Madison ($5,000), and Chase ($10,000, completing a full circle from 1862) were chosen in part because their faces were associated with financial and executive governance at the highest levels. The $100,000 Gold Certificate featuring Wilson was never intended for public circulation and served only as an interbank transfer instrument between Federal Reserve Banks and the Treasury.
These high-denomination notes were discontinued by Treasury Secretary Henry Morgenthau Jr. in 1945, with the Federal Reserve recalling them from circulation in 1969 under Nixon’s Treasury. Surviving examples are now extraordinary collectibles. A PMG Very Fine 30 example of the Series 1934 $10,000 Federal Reserve Note (Fr. 2231) has been realized at over $400,000 at major auction. The relative rarity of the $5,000 Madison note in any grade makes it one of the most aspirational pieces in American paper money collecting, with fewer than 350 known examples across all series.
| Series / Date | Denomination and Portrait | Approx. Known Population | Rarity |
|---|---|---|---|
| 1862 | $1 Legal Tender (Chase Portrait, Fr. 16) | Several hundred known | Scarce |
| 1869 | $1,000 Legal Tender (DeWitt Clinton, Fr. 187a) | Under 20 known | Key Date |
| 1886 | $1 Silver Certificate (Martha Washington, Fr. 222) | Moderate survivors | Scarce |
| 1891 | $2 Silver Certificate (William Windom, Fr. 246) | Fewer than 150 known in all grades | Rare |
| 1928 | $2 FRN Star Note (Jefferson, various districts) | Varies by district; Boston lowest | Scarce |
| 1934 | $5,000 FRN (Madison Portrait, Fr. 1973) | Under 350 known all series | Key Date |
| 1934 | $10,000 FRN (Chase Portrait, Fr. 2231) | Approximately 336 known | Key Date |
| 1934A | $500 FRN (McKinley, Fr. 2202) | Several thousand, mostly VF or below | Scarce |
| 1966 | $100 United States Note (Franklin, Fr. 1550) | Widely available in circulated grades | Common |
The Modern Era: Politics Returns to the Portrait Discussion
For decades after 1928 the portrait assignments seemed locked in permanence. But in 2016, Treasury Secretary Jack Lew announced plans to place Harriet Tubman on the $20 note, replacing Andrew Jackson. The proposal, which would have been the first portrait change on a circulating Federal Reserve Note in nearly 90 years and the first to feature an African American, generated enormous controversy across the political spectrum. The Trump administration delayed the redesign, citing security feature development timelines. Treasury Secretary Janet Yellen reaffirmed the commitment to the Tubman $20 in 2021, with a new target implementation timeline extending into the late 2020s pending the full NexGen currency redesign program.
For collectors, this ongoing saga has immediate implications. Series 2017A $20 Federal Reserve Notes featuring Andrew Jackson may ultimately represent the final series of a portrait assignment that has lasted since 1928. First and last series of any portrait era tend to attract collector premiums over time. The same logic applies to low serial number notes from the final Jackson-portrait series, which are worth setting aside in high grade.
Whenever a confirmed portrait change is announced, the last series before that change becomes historically significant. Consider setting aside high-grade, consecutively numbered pairs or small packs of Series 2017A $20 notes now, while they are still easily obtainable at face value. A sealed BEP souvenir folder containing the final Jackson $20 series will likely command a meaningful premium within a decade, similar to how the last large-size series notes spiked in collector demand after 1928.
Aesthetic Principles the BEP Applied Behind the Scenes
Beyond politics, the BEP’s master engravers imposed their own aesthetic criteria on portrait selection. The portrait had to exist in a sufficiently detailed and high-quality painted or photographic source. Intaglio engraving at the level required for currency demanded exceptional source material, because the engraver was translating light, shadow, and texture into thousands of hand-cut lines on a steel die. Portraits with poor source images were essentially disqualified on technical grounds.
This explains several choices that otherwise seem arbitrary. Daniel Webster appeared on the 1869 $50 partly because an excellent Gilbert Stuart-style painted portrait with strong contrast and clear modeling of the facial planes existed and could be translated successfully to steel. The BEP kept a reference library of approved portrait engravings, and once a portrait was successfully engraved, there was internal institutional pressure to reuse it because new engravings were enormously expensive and time-consuming, sometimes requiring a master engraver to spend 1,200 hours or more on a single portrait die.
Chief Engravers like Louis Delnoce and later George Rose and Joachim Benzing were key invisible figures in portrait history. Their technical assessments of what was engravable often functioned as a practical veto on portraits that politicians might have preferred but for which no suitable source material existed. Collectors who study proof and specimen notes from the American Bank Note Company archives, now accessible through Heritage Auctions and the Smithsonian, can sometimes identify rejected portrait trials that never made it to issued currency.
Conclusion: Why This History Matters for Your Collection
Every portrait on every US note is a fossilized political moment, an artifact of who held power, what aesthetic standards the BEP’s engravers could achieve, and what the Treasury Department believed about the hierarchy of American historical memory. When you hold a 1928 $10 Federal Reserve Note with Alexander Hamilton’s portrait in Fine or Very Fine condition, you are holding the physical result of a 1927 committee decision shaped by post-World War I economic nationalism, Andrew Mellon’s personal views on financial statesmanship, and the technical capabilities of a steel die engraver working in Washington DC. That context does not change the catalog value, but it fundamentally enriches the experience of collecting.
For new collectors, the practical takeaway is simple: portrait transitions mark the most historically significant series boundaries in US paper money. Learn which series represent a portrait’s first appearance and which represent its last, and you will have a reliable framework for identifying which notes deserve extra attention at shows and in dealer inventories. For advanced collectors, the pre-1928 portrait diversity in Legal Tender Notes, Silver Certificates, and Gold Certificates offers a lifetime of research into the political and aesthetic decisions that shaped one of America’s most widely encountered art forms.
