1909–11 T206 Charley O'Leary
Detroit Tigers · American League · 150-350 print series
The 1909–1911 T206 Charley O'Leary (“Portrait” pose) is part of the legendary “White Border” tobacco set — The Monster. This card depicts Charley O'Leary, a member of the historic Detroit Tigers (American League), and was printed in the 150-350 series, known with 6 tobacco-brand backs. Across PSA and SGC, roughly 1004 examples have been graded, with only 38 in NM 7 or better — a reminder of how tough this issue is in high grade.
About Charley O'Leary
Charles Timothy "Charley" O'Leary was a Chicago-born shortstop who reached the majors after playing semi-pro ball for a clothing company's team; recruited around 1900 by the White Stockings, his early promise was set back when Rube Waddell broke his arm with a pitch. He debuted with the Detroit Tigers on April 14, 1904, and served as their regular shortstop through 1907 before shifting to a utility infield role from 1908 through 1912. O'Leary was the starting shortstop on Detroit's 1907 club, the first pennant winner in franchise history, and he stayed aboard as the Tigers took three consecutive American League flags (1907-1909), losing the World Series each year. A light-hitting glove man, he batted .226 with just 3 home runs across eleven big-league seasons, closing his playing days with the 1913 St. Louis Cardinals. He later coached for years with the Yankees, Cubs, and Browns, winning World Series rings alongside Miller Huggins (1923, 1927, 1928). In one of baseball's great oddities, O'Leary pinch-hit for the Browns on September 30, 1934, singling and scoring at age 58 to become the oldest AL/NL player ever credited with a hit and a run. This is a common Tigers subject in the T206 350-460 print run, not a scarce card.
Sources: Wikipedia · Baseball-Reference · SABR
Confirmed backs (6)
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 | 616 | 30 | 32 | 84 | 148 | 104 | 127 | 91 |
| SGC | 388 | 8 | 7 | 45 | 67 | 89 | 74 | 98 |
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 | 118 |
| Piedmont | 114 |
| Sweet Caporal | 84 |
| Sweet Caporal 1909 | 70 |
| Piedmont 1910 | 44 |
| Sweet Caporal 1910 | 28 |
| Sovereign 1910 | 11 |
| Sovereign | 10 |
| Sovereign 1909 | 10 |
| El Principe de Gales | 8 |
| Old Mill | 6 |
| Hindu | 5 |
| Unknown back | 108 |
SGC by back
| Back | Graded |
|---|---|
| El Principe de Gales 1909-11 | 5 |
| Hindu 1909-11 | 5 |
| Piedmont 1909 | 161 |
| Piedmont 1910 | 58 |
| Sovereign 1909 | 9 |
| Sovereign 1910 | 18 |
| Sweet Caporal 1909 | 95 |
| Sweet Caporal 1909-11 | 1 |
| Sweet Caporal 1910 | 36 |
Frequently asked questions
What is the 1909-11 T206 Charley O'Leary card?
The Charley O'Leary (Portrait) 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 Detroit Tigers player and was inserted in cigarette packs across 6 different tobacco-brand backs.
How rare is this T206 card?
Across PSA and SGC, roughly 1004 examples of the Charley O'Leary have been graded, with only 38 grading NM 7 or higher, so mid-grade copies are obtainable while high-grade examples are genuinely scarce.
Which backs does the T206 Charley O'Leary come with?
The Charley O'Leary is confirmed with 6 tobacco-brand backs: El Principe de Gales, Hindu, Old Mill, Piedmont, Sovereign, Sweet Caporal. The back brand is a major driver of both scarcity and value.
Is the T206 Charley O'Leary 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.
Other poses of Charley O'Leary
More Detroit Tigers cards
- Donnie Bush
- Ty Cobb (Portrait - Green)
- Ty Cobb (Portrait - Red)
- Ty Cobb (Bat Off Shoulder)
- Ty Cobb (Bat On Shoulder)
- Sam Crawford (Throwing)
- Sam Crawford (With Bat)
- Wild Bill Donovan (Portrait)
- Wild Bill Donovan (Throwing)
- Hughie Jennings (One Hand Showing)
- Hughie Jennings (Two Hands Showing)
- Hughie Jennings (Portrait)
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 2026-08-28.