6 Wall Street veterans share the best trades they've ever made
Last month, Business Insider highlighted tales of investing glory from 10 everyday Americans. For some, their best investment was their house. For others, it was holding on to superstar stocks like Nvidia or Apple.
But what about the pros? Over the last few weeks, senior Wall Street money managers have regaled us with stories of their career highlights.
A degree of luck played a role in each trade, to be sure, but all of the anecdotes also highlight why top asset managers are among the best in their business: their ability to spot timely opportunities and capitalize on them, either in the short term or over many years.
GMO's Arjun Divecha used negotiating tactics at 3 a.m. to eventually realize a 6,400% return. Haverford Trust's Hank Smith knew to get out of a stock just a day before it fell 86%.
Here are the stories of the best trades six Wall Street veterans made, either through their firms or for their personal accounts.
Arjun Divecha, founder of GMO Emerging Markets Equity
In 1998, Russia experienced a financial crisis that caused its stock market to crash by 98% and sparked a brief global financial shock.
Divecha started buying up discounted shares of machinery producer UralMash, now known as United Heavy Machinery, amassing a 5% stake in the company.
One night, he got a call at 3 a.m. from a Russian investor who owned 2% of the firm and wanted to know if Divecha and GMO were interested in buying it.
"I said, 'Ok, what is the bid-ask on this?' because one of the first things you learn in a crisis is you never say, 'What's the price?'" Divecha said. "There's no such thing as a price in a crisis."
The investor was asking for a dollar a share, but the current bid was for 50 cents. Annoyed at being woken up, and knowing that several failed New York-based hedge funds were due to liquidate their shares in the company soon, Divecha said he would buy his stake for 23 cents a share and that the offer was good for a minute. The investor accepted.
"I am convinced that had I said 25 cents, he would not have taken it," Divecha said. "When I said 23 cents, I was using something I call the illusion of precision — that somehow he thought that I had done some complicated math and come up with 23 cents."
Divecha held the stock for four to five years before selling it for around $15 per share, he said.
Que Nguyen, CIO at Research Affiliates
During the pandemic in early 2020, when the price of oil went negative, Nguyen had an idea: Get paid to hold oil. However, it's hard for a retail investor to take delivery of physical crude.
Nguyen decided to approach the oil trade by gaining exposure to MLPs, or Master Limited Partnerships, which are generally companies that process and move oil. She did this via investments in specific ETFs. With the sector broadly cheap, casting a wide net made this the simplest approach.
"It's kind of like the question do you want to look for the needle in a haystack, or do you want to buy the haystack?" Nguyen said. "When the haystack is full of great needles, you just want to buy the haystack."
As it became clear that the world would normalize and reopen, her investment returned 50%. She eventually closed the position and transferred the proceeds to her donor-advised fund, which allows someone to set aside money they intend to donate.
Nguyen's favorite charities to donate to include those focusing on education and food security in New York City.
Bill Smead, manager of the Smead Value Fund
Amid the chaos of the 2008 crash, Smead — a top 1% investor, according to Morningstar data — noticed eBay trading at $11 a share and saw a bargain.
While he liked the business model, Smead was more drawn to the fact that the company owned 100% of PayPal, 100% of StubHub, and 30% of Skype. They also had the equivalent of $3 per share in cash and were debt-free, he said.
At Thanksgiving that year, Smead had a broker who was a family friend over, and remembers telling him about the stock.
"I said, 'When you go back to your office on Monday, you call every single one of your clients and get them to buy a bunch of this stock and then never sell it," Smead said.
Today, eBay trades at around $77 a share, and PayPal has split into a separate stock.
John Barr, manager of the Needham Aggressive Growth Fund
Barr, whose fund has a five-star rating from Morningstar, said his best investment ever was in Nova (NVMI), a company that produces measurement systems used in the factory production of semiconductors.
It's benefited hugely from the recent semiconductor boom amid the AI arms race.
Barr bought it all the way back in the third quarter of 2009. Since then, it's up more than 6,000%.
"It was no analyst coverage, nobody knew it," Barr said. "I knew one of their peers very well, and the peer was also a small-cap listed company that was doing great, and I owned it."
Jason Hsu, CIO and founder at Rayliant
In early 2021, retail traders blew up hedge fund Melvin Capital by piling into GameStop stock, sparking a now-infamous short squeeze.
Hsu saw the Melvin collapse as an opportunity, as it likely signaled upside momentum on GME would run out quickly. It's not often that retail traders topple a hedge fund, so it seemed like a sign of the peak was near.
He took the same position that rattled other short sellers and bet against GameStop. He timed it just right.
As the stock fell 87% over the next couple of weeks, Hsu realized huge returns.
"I was right in the analysis assessment, but I was no more right than the hedge fund that went ahead of me," Hsu said. "We did the same analysis, and I made the money by actually being late, which is not usually an attribute that's successful in this industry."
He continued: "What I learned is if you do your analysis correctly, that's a part of investing successfully. Luck is so important. In that trade, if you're early, you die."
Hank Smith, head of investment strategy at Haverford Trust
Haverford Trust
Smith's best investment decisions were actually deciding when to sell during the Great Financial Crisis.
In October of 2007, Citigroup's stock fell 21% in the span of a couple weeks after a bad earnings report. Smith sold the stock, sparking ire from his clients.
"We were vilified by many of our clients for selling a bluechip company at the low," he said. "In fact, one consultant used that as an excuse to pull a handful of his clients that were invested with us."
But Smith had made the right move. Citigroup's stock continued its freefall as the crisis unfolded. Today, it's still down 79% from its price in early November 2007.
In September 2008, Smith then sold AIG at a steep loss before it collapsed by another 86% within a day.
"We sold the entire position in one day at around $15 a share," he said. "The next day it opened at $2."
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