1909-11 T206 Jack Chesbro
1909–11 T206 Jack Chesbro
New York Highlanders · American League · 150-350 print series
The 1909–1911 T206 Jack Chesbro is part of the legendary “White Border” tobacco set — The Monster. This card depicts Jack Chesbro, a member of the historic New York Highlanders (American League), and was printed in the 150-350 series, known with 5 tobacco-brand backs. Across PSA and SGC, roughly 1489 examples have been graded, with only 20 in NM 7 or better — a reminder of how tough this issue is in high grade.
About Jack Chesbro
Jack Chesbro was a spitballing right-hander whose 1904 season remains one of the most remarkable in baseball history. Born in North Adams, Massachusetts, he broke into pro ball with Albany of the New York State League in 1895, then worked through minor-league stops (including Richmond of the Atlantic League) before Pittsburgh purchased him in July 1899. He blossomed with the Pirates, going 28-6 in 1902 while leading the National League in wins and winning percentage as Pittsburgh took the pennant. After jumping to the New York Highlanders (later the Yankees) in 1903, Chesbro authored his legend in 1904: a modern-record 41 wins and 48 complete games, including 14 straight victories. That season ended in heartbreak when his wild pitch on the final day let Boston clinch the pennant. Nicknamed "Happy Jack" for the cheery grin he showed while working at a Middletown, New York mental hospital, he retired 198-132 with a 2.68 ERA and was elected to the Hall of Fame in 1946.
Sources: Baseball-Reference · SABR
Confirmed backs (5)
Chip colour marks each back's rarity tier. See the full T206 back rarity ranking →
Population (PSA · SGC)
| Grader | Total | NM 7+ | 6 | 5 | 4 | 3 | 2 | 1 & Auth |
|---|---|---|---|---|---|---|---|---|
| PSA | 837 | 18 | 27 | 87 | 177 | 154 | 194 | 180 |
| SGC | 652 | 2 | 3 | 58 | 89 | 115 | 136 | 249 |
NM 7+ bundles grades 7–10; 1 & Auth bundles grade 1, 1.5 & Authentic. Totals are subject-level (summed across all backs). Population as of 2026-06.
PSA by back
| Back | Graded |
|---|---|
| Piedmont 1909 | 192 |
| Piedmont | 184 |
| Sweet Caporal | 92 |
| Sweet Caporal 1909 | 71 |
| Sweet Caporal 1910 | 39 |
| Piedmont 1910 | 28 |
| El Principe de Gales | 26 |
| Sovereign 1909 | 13 |
| Old Mill | 9 |
| Sovereign | 5 |
| Unknown back | 178 |
SGC by back
| Back | Graded |
|---|---|
| El Principe de Gales 1909-11 | 25 |
| Old Mill 1909-11 | 8 |
| Piedmont 1909 | 358 |
| Piedmont 1910 | 49 |
| Sovereign 1909 | 15 |
| Sweet Caporal 1909 | 150 |
| Sweet Caporal 1909-11 | 1 |
| Sweet Caporal 1910 | 46 |
Frequently asked questions
What is the 1909-11 T206 Jack Chesbro card?
The Jack Chesbro is one of 524 subjects in the T206 "White Border" tobacco set issued 1909-1911, the hobby's most iconic vintage set (nicknamed "The Monster"). It pictures the New York Highlanders player and was inserted in cigarette packs across 5 different tobacco-brand backs.
How rare is this T206 card?
Across PSA and SGC, roughly 1489 examples of the Jack Chesbro have been graded, with only 20 grading NM 7 or higher, so mid-grade copies are obtainable while high-grade examples are genuinely scarce.
Which backs does the T206 Jack Chesbro come with?
The Jack Chesbro is confirmed with 5 tobacco-brand backs: El Principe de Gales, Old Mill, Piedmont, Sovereign, Sweet Caporal. The back brand is a major driver of both scarcity and value.
Is the T206 Jack Chesbro valuable?
Value depends heavily on the back brand and the card's grade: common backs in low grade trade modestly, while scarce backs and high grades command strong premiums. Check the current T206 Cards listings and eBay options above for live pricing.
More New York Highlanders cards
Sources: t206resource.com, Baseball-Reference, PSA & SGC population reports, and Inside T206 by Scot Reader. Card data & population compiled and maintained by T206Cards.com. Page last updated 2026-07-01.