This is a one of a kind portrait of New York Yankees "Iron Horse", Lou Gehrig.  It is a charcoal rendering on brown craft paper.  It was drawn in 1935 at "Old Florida" London by an artist named "Alec". It is obvious that Lou Gehrig had this portrait drawn for a specific person named George.  The inscription on the portrait reads:
To George-
In fond memory-
and-
May I always 
be deserving 
of your
 friendship. 
Sincerely
Lou Gehrig
It is my belief that the portrait was drawn for Babe Ruth but never given to him.  The reasons I believe this are many.  I have spent the past 30 years researching the relationship between Lou Gehrig and Babe Ruth.  I have spoken to Ray Robinson (author of 'The Iron Horse'), and the folks at Cooperstown Baseball hall of fame.  Both told me the portrait could not have been for Babe Ruth because  he and Lou Gehrig were not speaking to each other at the time. Ray Robinson also pointed out that no one ever called  The Babe by his given name "George" but either Bambino or Jidge.

All excerpts and quotations (with exception to reference to Old Florida) in the following are from and article by Tara Krieger at https://sabr.org/journal/article/babe-ruth-and-lou-gehrig/

It was "Jidge" that sparked my curiosity.  Where did it come from? My research told me that when Lou first joined the Yankees he and Babe were really close. "Ruth became a frequent dinner guest of Mom and Pop Gehrig, who bonded with him because he could converse in their native German. One day he gifted them a Chihuahua, and Mom Gehrig named it Jidge, a corruption of “George,” which Ruth’s clubhouse and card-playing buddies sometimes used."(https://sabr.org/journal/article/babe-ruth-and-lou-gehrig/)

"When Ruth’s estranged first wife, Helen, died in a fire in the winter of 1929, Gehrig sent him a letter of “heart-felt sympathy,” addressing Ruth as “George.” He wrote, “May the Almighty grant you and Dorothy sufficient strength to bear up during your bereavement. Your sincere friend, Lou Gehrig. Key West, Florida, where happiness reigns on a fishing trip I wish you shared.”59" (Boston Herald, January 16, 1929, reprinted in Sarnoff, 200.)


"The “feud” between Gehrig and Ruth is often simplistically attributed to a dispute arising from Mom Gehrig’s offhanded comment about Claire Ruth not dressing her stepdaughter, Dorothy, as nicely as her biological daughter, Julia. An offended Claire relayed the remark to her husband, who confronted Gehrig about it. “Tell your mom to mind her own business!” Ruth said. Well! Nobody insulted Lou’s mother! And the two supposedly never spoke again."(https://sabr.org/journal/article/babe-ruth-and-lou-gehrig/).


But, on and off, over many years they did speak.  How could they not?  Road trips, dug-outs......Lefty Gomez, a teammate starting in 1930, claimed that much of the Ruth-Gehrig rift was inflated rhetoric. “You keep hearing these stories about Babe and Lou not hitting it off,” he recalled.  “When you consider ballplayers are together from February until October, there are going to be squabbles. But Babe and Lou enemies? Not a chance. Babe was an extrovert in the extreme and Lou was an introvert. Babe threw his money around and Lou counted his pennies. Babe liked the high life and Lou enjoyed the opera and the philharmonic. Babe was glib with the press; Lou found it hard to come up with a snappy quip. There may have been comments here and there that caused temporary chagrin, but Babe and Lou were teammates and friends on and off the field. The press created a feud between Ruth and Gehrig that I never saw. Babe and Lou were both dear friends of mine as well as teammates, and I respected the fact that they lived life their own way. Nothing more, nothing less.”63 (Vernona Gomez and Lawrence Goldstone, Lefty: An American Odyssey (New York: Ballantine Books, 2012), 184-85.


The 1934 All-Star Goodwill Tour of Japan did cause a rift between Lou and the Babe."The goodwill tour of Japan the previous winter – featuring Ruth, Gehrig, and 13 other American League stars – widened the rift. The pair must have been on speaking terms beforehand, as Ruth lent the stingy Gehrig $5,000 at the outset of the tour to last him until his paycheck.66(Leavy, 413.)"


"But on the ship across the Pacific, something went wrong. It happened when Claire Ruth crossed paths one day with Eleanor Gehrig, Lou’s wife of about a year. They pooh-poohed whatever bad blood there was between their husbands, and Claire invited Eleanor back to their cabin. The Babe was waiting, and alcohol was involved. Innocent revelry may have been all that occurred.68(Rumors of an affair between Babe Ruth and Eleanor Gehrig are unsubstantiated speculation.)


"But Lou was worried sick that his new bride had disappeared for several hours, and The Babe was the source of his fury. Gehrig coldly blew off Ruth’s peace offering.69(See Eleanor Gehrig and Joseph Durso, My Luke and I (New York: Thomas Y. Crowell Company, 1976), 189-90. June O’Dea Gomez, Lefty’s wife, noted in her journal that she spent a night drinking with Claire Ruth and Eleanor Gehrig on the same Japan trip. Whether that was before or after the incident in the Ruths’ cabin is unclear. Gomez and Goldstone, 185.)"


"Dorothy Ruth Pirone said in her memoir that Ruth did visit Gehrig “often” as his health deteriorated, over Claire’s objections."


"When Ruth learned of Gehrig’s death at age 37 on June 2, 1941, he broke down. “No, no … this is terrible, terrible news. It can’t be true,” he said. “I knew how ill Lou was, but I think all of us hoped, even against hope, that he would fight his way out. “Lou was like a son to me. When illness forced him to retire, I was as heartbroken as he was. Believe me when I say his memory should always be kept green as an inspiration to all of us.”81 (“Babe Ruth Cries When Informed of Death,” International News Service, Syracuse Journal, June 3, 1941.)


After The 1934 All-Star Goodwill Tour of Japan both Lou and the Babe did not return directly to the USA.  Both extended their tours and eventually ended up in London, England.  The "Old London" was  "the Florida Club, London, 1926 - a famous cabaret venue famous for its glass floor.One nightclub that features strongly in a variety of memoirs is the Florida. It was situated in South Bruton Mews, off Berkeley Square, and was open from at least 1926, with the odd interruption, through to 1940. It was very much at the upmarket end of London social life. Formal dress was required and the clientele was drawn almost exclusively from “Society”. Angela Worthington (later Fox) and Lady Marguerite Strickland were particularly taken by the place, not least because of the telephones at each table, which allowed for all kinds of flirtation."https://elvirabarney.wordpress.com/2012/03/16/florida-club-5-south-bruton-mews/


Lou Gehrig was a quiet and sentimental guy with a real stubborn streak.  I believe that through his wife Eleanor's encouragement he had this portrait done as a means of making amends with Babe after the fiasco aboard the ship on its voyage to Japan.  But, the question remains; Did Lou ever actually give the portrait to Babe?  

If you look closely at the back of the portrait you will notice two things.  The first is that it was accordion folded (the creases are still evident).  I believe the Lou hesitated and did not give the portrait to Babe and kept it stored between the pages of a book for the trip back to New York.

The second important thing to note on the back of the portrait are the obvious crinkle marks.  This tells me that the portrait was crumpled up in someones hand and thrown in the trash.  What I truly believe is that either Lou disposed of it or, perhaps he did give it to Babe and Babe disposed of it.  Either way I believe, beyond any doubt that the "George" named on the portrait is George Herman Ruth.