It's often said in sports that it's better to be lucky than good.
For former prosecutor William Dowling, a chance encounter with the late New York Yankees owner George Steinbrenner sparked a career-changing job as general counsel to the prestigious baseball team. That later led to a position as president and chief executive officer of the New Britain Rock Cats, an Eastern League Double A affiliate of the Minnesota Twins.
"I was fortunate to have met certain people," said Dowling, "and the rest is history."
And while he runs a successful minor league team, Dowling is also known in the legal community for freely sharing his knowledge. In recognition of his imprint on sports law in the state, the Connecticut Bar Association's Sports and Entertainment Law Section last month gave Dowling its first ever Sports Lawyer of the Year award.
Section chair Don P. Tutson Jr. said Dowling has helped him as he's developed a practice that includes sports law. One of Tutson's early clients was former University of Connecticut basketball star Ray Allen.
"I got to know Bill just being around the area," said Tutson. "When I told him what I was doing, he literally threw his office door open and invited me in any time I had a question. Ever since he made the mistake of saying, 'If you ever have a question let me know,' he's heard from me for the last decade."
Tutson continued: "This guy understands it's not only about the business of law but developing lawyers. That's really what the award was about."
Dowling graduated from Columbia University and then attended Boston College for law school. He soon went to work as an assistant district attorney in Manhattan. After a few years there, he worked as chief of the criminal division in New York's Attorney General's Office from 1979 to 1985.
In the mid-1980s, his office began investigating a scheme by various big-ticket item retailers who were helping customers avoid paying New York sales taxes by taking advantage of a loophole that allowed out-of-state residents to avoid paying the tax. For instance, hotel owner Leona Helmsley was accused of buying $485,000 worth of jewelry and walked out with the items without paying sales tax worth $40,000. Instead, an empty box was mailed to a Connecticut residence.
"We convicted folks higher up in these companies," recalled Dowling. "New York State was losing a tremendous amount of money because of this."
Dowling said several celebrities were brought in as witnesses to testify that they had purchased big-ticket items at certain retailers and were offered the opportunity to evade the sales tax. One of those witnesses was George Steinbrenner.
Dowling was a diehard Red Sox fan growing up. "I hated the Yankees at that point," he said. But as a baseball fan, he was still interested in meeting Steinbrenner when he arrived to testify.
Dowling said the two exchanged pleasantries and had a short conversation.
"[Steinbrenner's] lawyer called the next day and said, 'Do you want to be Yankees general counsel?'" recalled Dowling. "I slammed the phone down and thought a friend of mine was playing a trick on me."
Turns out it was no trick. There was a legitimate opening for the head Yankees' lawyer, and Steinbrenner had just held extensive interviews with two clients. But there was something about Dowling that he liked.
"Something clicked in his head and they offered me the job," said Dowling. "It was a very difficult decision for me in a lot of ways. I was doing quite well in public service. I was on my way to being a judge in a few years…"
By January 2, 1986 Dowling had a big office overlooking Yankee Stadium. "Basically I was [Steinbrenner's] right-hand man," said Dowling. He was responsible for reviewing all labor agreements, player contracts, and television and radio deals. Any litigation involving the Yankees went through him.
Having spent his career in criminal law, there was an adjustment period. "All of a sudden I come into a ballclub where most of the work is civil in nature," said Dowling. "I was a little bit naïve thinking I could easily switch from civil to criminal. It made me very uneasy over some matters."
Fortunately, Dowling had that large Yankee budget to work with so he was able to bring in outside counsel to provide greater expertise in many matters.
By 1988, Dowling had left the Yankee front office to take a law firm job at Wachtel Missry, also in New York City. Dowling still handled matters for the Yankees as outside counsel but by the early 1990s, after Steinbrenner served a two-year suspension from baseball, the franchise "cleaned house," Dowling said.
But the experience was invaluable. He went on to serve as an agent for several National Hockey League players and then he and Coleman Levy, another attorney, bought the New Britain Rock Cats in 2000.
Dowling not only had an ownership interest, he also served as the club's president and CEO. One budget saver: not needing to hire a lawyer to handle all the team's legal matters.
His legal background helped him finalize concession sales agreements; deals between the team, Major League Baseball and the Minnesota Twins; and the lease agreement with the city of New Britain. Also, despite his duties with the Rock Cats, Dowling still remains of counsel to Wachtel Missry, though he acknowledged he's decreased his workload there significantly the past couple years.
Dowling helped a struggling franchise regain popularity and attendance.
"Old ownership didn't do any serious marketing," said Dowling. "Early on most of our [advertising] money was spent on shows that women and kids watch. They make the decisions on spending discretionary money. So we placed ads on Nickelodeon, Oprah…We had the worst team in the league the first year, 40 games under .500, but we increased attendance by 50,000 people more than previous ownership ever had in a season. We knew at that time we were on to something."
By 2006, the 6,146-seat New Britain Stadium was routinely drawing 350,000 fans a season spanning 71 home games. The peak came in 2011 when they drew 367,000 fans.
Last year, Dowling and Levy sold the team to a group of New England-based investors. Dowling still has an ownership interest in the team, though considerably less, and stayed on this season to serve as president.
He said he would talk to the majority owners after the season but that it's unlikely he will stay on as president. "I'm always looking for new things to do," said Dowling, whose legal career reached its 40-year anniversary this year. "I'll keep my eyes open for a team around here that might be available."
Dowling also serves on the board of directors for the United Way of Central and Northeastern Connecticut. "I feel like it's time to give a little more back to the community," Dowling said.
Meanwhile, in a response you don't often hear out of the mouth of a baseball fan in New England, Dowling said he now roots for both the Red Sox and the Yankees, depending on which team is having a good season.
"But if my life was on the line, I'd say I'm a Twins' fan."•