The Messy History Of Charlie Sheen's "Winning" Ring

As part of his relentless media odyssey this week, Charlie Sheen introduced himself to Twitter with a message that had a Chappelle-esque, "Kiss the rings, bitches" quality to it. It was an image of Sheen's shimmering 1927 World Series ring that was once worn by another winner with an equally insatiable appetite for showgirls and booze: Babe Ruth.

Sheen, a noted baseball relic collector for decades, is the former owner of some of the hobby's most storied items, including the 1986 World Series' "Mookie Ball" and Bill Buckner's glove that missed it. Reports had Sheen beating out baseball nerd Keith Olbermann for the Mookie Ball at auction with a bid of 85 grand. At the time, Sheen told the New York Daily News, "I was (only) going to go to $50,000, but my ego got in the way."

Over the years, as he floated in and out of rehab, Sheen ended up selling the majority of his collection, but he retained the holy grail, Ruth's '27 World Series ring, and he doesn't hesitate to show it off. A few weeks ago, Sheen hosted a screening of Major League for some select friends and former MLB players, including Hall of Famer Eddie Murray, Lenny "Nails" Dykstra and Todd Zeile. The guests all got the opportunity to try on the Bambino's ring,

Industry experts estimate that the ring's value would approach half a million dollars if it ever hit the auction market. In 1999, Sotheby's sold what was believed to be Lou Gehrig's 1927 ring for $96,000. The ring originated from the then-famous collection of super-collector (and Yankees limited partner) Barry Halper.

That's where the mystery of Sheen's ring comes in.

The Messy History Of Charlie Sheen's "Winning" Ring

Halper died in 2005. Once revered as the granddaddy of baseball memorabilia collecting, he has recently been exposed as a trafficker in stolen and non-genuine artifacts, including items he sold to Major League Baseball in a $7 million transaction in 1998. Fraudulent items include "Shoeless" Joe Jackson's 1919 Black Sox jersey, Mickey Mantle's 1951 rookie jersey, Ty Cobb's 1946 diary, and several alleged autographed items by Babe Ruth. Other items sold at Sotheby's in 1999 have been confirmed as stolen from institutional collections, among them the Baseball Hall of Fame, Hawaii's state archives, and the New York and Boston public libraries.

Sheen acquired Halper's Ruth ring in a 1990s deal with auctioneer Josh Evans of Lelands. Sheen told Sports Collectors Digest in 2000 that he'd never met Halper and that his deals with him came "by way of Evans" (more on that later). Back in those days Halper's items possessed an extra cachet due to his legend and celebrity, but now collectors and observers are examining all of the Halper holdings with far greater skepticism, including big-ticket items like Sheen's 1927 Ruth ring.

The controversy over Ruth's rings begins with the Ruth family and their claims that all of the Babe's treasured rings — the ones from 1923, 1927, 1928, and 1932 — at some point mysteriously disappeared.

The Messy History Of Charlie Sheen's "Winning" RingS

In 1988, the Babe's daughter, Dorothy Ruth Pirone, wrote the following in her book, My Dad, The Babe:

Through the years, various priceless heirlooms of Babe's have vanished, the most upsetting of which was the disappearance of most of his World Series rings. Unfortunately, incidents of that nature have caused me to be much more guarded around strangers.

Pirone clearly stated she never had the rings in her possession and that, to the best of her knowledge, they had gone missing. Her daughter, Linda Ruth Tosetti, tells me: "She had not seen the rings since her father died in 1948. She was looking for them and Claire Ruth [Babe's second wife] later told her, the year before she died, that they were in a safe-deposit box."

Two years after the release of Pirone's book, it emerged that Barry Halper owned the 1927 ring. In a Sports Collectors Digest interview with Halper conducted by Josh Evans for his "Balls in the Attic" column, Halper rattled off the top 10 items in his collection. Evans wrote:

8) Babe Ruth and Lou Gehrig's 1927 New York Yankees World Series Rings. The Ruth ring was obtained directly from Dorothy Ruth Pirone, his daughter. Lou Gehrig's was purchased through an ad in the New York Times. 'This pair is as important to the true collector as anything in the Smithsonian,' says Barry."

Linda Ruth Tosetti calls the above claim "an out-and-out lie," reiterating that her mother "never saw those rings after her father died."

Was Barry Halper caught in another lie about one of his treasures?

The Messy History Of Charlie Sheen's "Winning" Ring

Halper's statement could not be corroborated by the Babe's daughter; Dorothy Ruth Pirone died on May 28, 1989. According to her obituary in The New York Times, she was 59 years old when she discovered the true identity of her mother: It wasn't the Babe's first wife, Helen, but rather Juanita Jennings, "a woman she had grown up knowing and loving as a close family friend." After Babe died in 1948, things went sour between Dorothy Ruth Pirone and her sister on the other side of the family, Julia Ruth Stevens. Babe Ruth's last will and testament (which has been stolen from a New York City courthouse) was contested in the 1950s.

So how could Barry Halper have purchased the 1927 ring from Dorothy Ruth Pirone if she hadn't seen them since 1948? And where are the other rings, from 1923, 1928 and 1932?

This week, to confuse matters even more, a longtime Halper friend and associate, Rob Lifson, president of Robert Edward Auctions, wrote the following on a collector internet forum known as Net54:

Interesting note: the 1927 Yankees Babe Ruth ring came from Barry Halper who got it directly from Mrs. Ruth. He sold (or traded) it in the 1990s.

He was referring to the Babe's widow, Claire Ruth. In her 1988 book, Dorothy Ruth Pirone recalled Claire's relationship with collectors:

Collectors have obtained numerous items of my father's courtesy of Claire: uniforms, jewelry, clothing, bats, golf clubs, fishing equipment—you name it. Customarily family heirlooms are passed down from generation to generation; they should not be in the hands of private collectors.

Halper was known to have visited and made purchases from Claire Ruth while she was still living in an apartment on Riverside Drive in Manhattan. Ruth's granddaughter has heard stories about Halper visiting Claire with bottles of liquor. Says Linda Ruth Tosetti: "I was told he'd get her liquored up and then walk out with some of Babe's stuff." It's not an unreasonable suggestion. In 1999, Halper told The New York Times that he swapped six bottles of J&B Scotch with Lou Gehrig's widow in exchange Lou's "Luckiest Man on Earth" uniform from 1939. Halper said Mrs. Gehrig was happy to get some "hooch."

It's possible that Halper (or someone else) purchased the ring from Claire in a similar fashion. But if he did, why say in 1990 that he'd purchased it from Dorothy Ruth Pirone?

Needless to say, Linda Ruth Tosetti is troubled by Halper's accounts. "Just the idea that he gave multiple explanations makes me suspicious (about) how he really obtained the ring," she says. "And where are the others? And what's to say it's not a fake, since Halper had so many of those, too?"

The Messy History Of Charlie Sheen's "Winning" Ring

It's no surprise that items related to baseball's greatest drawing card are among the missing. Over the years, we've learned that Halper once owned Ruth's 1925 separation agreement from his first wife, which was stolen from a New York courthouse; his last will and testament from 1948 (also stolen); signed affidavits from lawsuits (stolen); the mortgage for his Massachusetts home (stolen); and even his autopsy report (stolen).

Says Linda Ruth Tosetti: "Do you know Babe's autopsy report is missing from Memorial Sloan Kettering Hospital as well as every piece of paper that [said] he was ever there? And that they know who has Babe's stolen will but the FBI still hasn't gotten it back? What are the odds his rings weren't stolen either? It's a travesty."

Considering the recent controversy over Halper's authenticity issues, the Babe's granddaughter also wonders if Sheen's ring is even the real deal. "We see Halper sold fake items to the Hall of Fame," she says. "With the lies of how this ring was obtained, how do we know my grandfather's 1927 ring isn't fake?"

Linda Ruth Tosetti also points out that Halper sold another 1927 Series ring attributed to Lou Gehrig at Sotheby's in 1999. "I saw Lou's 1927 ring cap on display in the Hall of Fame on a bracelet he made for his wife," she says, "so how could Halper have had his ring, too?"

Creating a fake isn't difficult. All one would have to do to create a Ruth or Gehrig 1927 ring is find an authentic example given to a lesser player and then have an expert engraver replace the original name with "Ruth" or "Gehrig."

The Messy History Of Charlie Sheen's "Winning" RingS

But Josh Evans of Lelands is confident that Sheen's Ruth ring is legit. Says Evans: "The ring itself is 100 percent correct. The 'Babe Ruth' name engraved inside is exactly the right font for the 1927 rings and is vintage to the period." Evans also tells reveals to me that he acquired the ring from Halper. "When I purchased it from Barry Halper," he says, "I relied on the piece itself, not on any story he told me of its provenance."

To the possibility that Sheen's ring was stolen from Ruth's family, Evans responds: "If Claire or Dorothy or anyone else sold these, it is a reality of the memorabilia world. All those years ago there were no price tags." That's not to say he doesn't sympathize with Ruth's relatives. "It does not make families being left with little or no compensation any less tragic."

For now, the Babe's '27 ring rests comfortably in Charlie Sheen's sprawling California spread, along with his "porn star family," 7-gram crack rocks, tiger blood, and Adonis DNA, as suitable a home as any for a baseball relic with an unseemly past. Maybe it is a forgery; maybe it is the genuine ring of a Yankees benchwarmer. But the funny part is, it's undoubtedly a lot more valuable now than any sports jewelry like it. After all, it's Charlie Sheen's "Winning" ring. What collector wouldn't want to get his hands on that?

Peter Nash, formerly Prime Minister Pete Nice of Def Jam's 3rd Bass, is the author of two baseball books and also writes for Haulsofshame.com. He is currently working on his upcoming book, Hauls of Shame: The Cooperstown Conspiracy and the Madoff of Memorabilia.