If you were cheering for the Blue Jays last fall, as so many Canadians were from coast to coast, you can thank Herb Solway, JD 1955, a former chair of the club, and one of Toronto’s legal titans who helped bring the baseball team here in 1977.

By Tim Hutzul, LLB 1995 / Photography by Dan Bannister

From the Fall/Winter 2015 issue of Nexus

Herb Solway, JD 1955How many alumni have had a future Hall of Fame and Super Bowl quarterback debate whether to shun the National Football League in favour of Toronto with Herb in his home office?  Or had a senior sports executive compare him favorably to a character from the movie The Sting, praising Herb’s ability to get what he wants—while letting the other guy think he won?  

Herb will forever be linked to his important role in bringing the Blue Jays to Toronto, as brilliantly told in the documentary What if—the Unlikely Story of Toronto’s Baseball Giants, written by Sportsnet’s Stephen Brunt.  It’s must-see TV for any Toronto sports fan—how Solway helped a group of “cock-eyed optimists who knew less about baseball than they should have” to secure a major league franchise. In the process, Brunt credits the group with unintentionally bringing about the end of the commissioner of baseball as an all-powerful “Tsar,” a role dating back to Commissioner Landis and the “Black Sox Scandal,” when eight White Sox players were accused but later acquitted of game fixing in exchange for money from gamblers.

“It was only years later,” says his son Gary Solway, LLB 1983, “that I truly appreciated a childhood spent at spring training and football camps with unparalleled inside information and access.  As a kid, it was just Dad’s job.”  

Herb’s influence continued beyond winning the franchise. Former Jays executive Paul Beeston calls Herb a “true and loyal friend,” a man with the “mind of a chess player,” which is likely why every executive since the start of the franchise called upon Herb for counsel and advice, he adds. This institutional knowledge has had a profound influence on the success of the club. Jays insiders joke Solway is the “Designated Fretter,” always worried about some detail and Beeston can’t resist making a dig. Herb fancies himself “the game’s ultimate strategist,” says Beeston with infectious enthusiasm.  “He can tell you what pitch to call.” 

Former general manager Alex Anthopoulous says he went to Herb for advice on a variety of issues, including player trades (does that qualify as billable?) and that “he feels lucky to have worked with Herb,” and to have had a chance to be his friend—a widely shared sentiment across many walks of life.

Herb Solway—lawyer, firm leader, mentor, raconteur, philanthropist, business executive and perhaps most importantly, friend. A man beloved by several generations of University of Toronto law students and lawyers, not to mention Toronto politicians, media and sports executives.


Last fall, I was back at Flavelle House for my 20th anniversary reunion. The event is a blast. I quickly run into old friends and a number of my professors. Warm greetings are exchanged. We lie to each other about how we haven’t aged. Ed Iacobucci, the newly announced dean at the time, gives a good and appropriately short talk during which I recall that in second year my roommate and I predicted his future ascension to dean. The evening is off to a great start when across the room I see Herb Solway, founding member and patriarch of Goodmans, Blue Jays ringleader and, importantly to me, the last person I interviewed with during articling week (it was probably less memorable for Herb).

Herb is here for his 60th anniversary reunion. Maybe it is seeing old friends, or seeing the man I associate with being offered my first “grown up” job, or the fact that the Jays are back in the playoffs for the first time since law school, but suddenly I feel nostalgic. Old memories flood back: friends, law school, the Duke of York pub (where appropriately the Class of 1995 is headed after the reunion reception).  Seeing Herb, several thoughts cross my mind.  First, the intersection of 20th and 60th reunions, Herb’s many accomplishments and the Jays’ return to glory deserve a Nexus profile. Second, at the risk of being superficial, damn Herb looks good.  It might just be me but I swear that the man has not aged in 20 years.

A short time after the reunion and still feeling nostalgic, I get the school to sign off on a Herb Solway story.  Wishing to reconnect with Herb, I volunteer to write it. Catching up with him proves great fun. He is how I remember him—witty, thoughtful and charming, generous with his time and impressive rolodex. A wide range of his friends and colleagues are only too happy to talk about Herb. They praise his intellect, judgment, loyalty, sense of humor and humility. People repeatedly cite the positive impact he has had on their lives (more on that later) and how much they treasure his friendship. As we get older, reunions provide an opportunity to reflect.  Hopefully, each of us can look back proudly and see someone or something upon which we have made a difference or had a profound influence. Herb Solway’s list could fill an entire full-length feature. The incomplete list includes the U of T Faculty of Law, the Blue Jays, Goodmans, directorships at Sun Media, John Labatt, and currently Gluskin Sheff, along with literally dozens of individuals—some well-known and others less so. He tackled issues when society turned the other way, helping to raise millions for mental illness and addiction for the CAMH Foundation and its precursor, the Clarke Foundation, with more than 20 years of dedicated support. Talking to people about Herb gives you a sense of how remarkable a man he is.

Everybody has a Herb story. Some, fortunately, are even on the record.

“Not only is his career a wonderful example of what our alumni can and do achieve,” says Dean Iacobucci, “I especially appreciated hearing his stories of Dean Wright and his colleagues, figures who are, to me, larger than life. It doesn’t hurt that he’s got a great sense of humour, is an excellent raconteur, and that we first got together to chat in his fantastic seats at the Jays game.”

Listening to Herb talk about the early days of U of T Law is wonderful, a chance to travel back in time.  His passion for Dean Wright, the early faculty, and classmates such as RJ Grey, is evident. Time goes too quickly, as Herb tells tales of founding law school dean “Caesar” Wright challenging students, and of his commitment to excellence. Herb laments today’s students and lawyers might not fully appreciate Wright’s visionary contributions to the law school. “We were,” chuckles Herb, “the little school that could.”

Everybody has a Herb story. Some, fortunately, are even on the record. Many, like former Premier and Liberal Leader Bob Rae, LLB 1977, elect to keep their stories private. “I won’t tell if Herb doesn’t,” quips Rae.    

Allan Leibel, LLB 1970, vividly recounts an event where a standing-room only crowd had gathered to hear firm co-founder Eddie Goodman speak as the guest of honour.

“Picture the Imperial Room of the Royal York Hotel, about 35 years ago. A charity dinner with 1,000 guests, all in tuxedos and gowns. Toronto’s elite. Eddie is at the microphone, and rambling more than a bit in his speech, as he tries to counter his introducer’s light-hearted attacks,” recounts Leibel. “From the edge of this huge room, a young Herb Solway stands up and shouts: ‘Mr. Goodman, do you have any prepared remarks this evening?’ It brought the house down. Who else but Herb,” Leibel marvels, “would have the courage, wit and cadence to pull it off?”

“Herb is in the DNA of Goodmans,”says partner Logan Willis, JD 2006.  “All of us here continue to enjoy his involvement and his wisdom” says firm chair, Dale Lastman. Lionel Schipper, LLB 1956, credits Solway with the strategic vision to recruit the best students as integral to the future success of the firm.  “See-in-the-dark smart,” says Schipper. “Recruiting is in his blood.” Adds Catherine Chang, LLB 1988, the firm’s alumni relations director, he has “a special knack for reading people.”

Lessons on how to treat clients and the endless possibilities of the legal profession; pep talks and career advice; positive encouragement and loyalty; trips to Palm Beach and Jays games; thoughtful gestures for spouses and kids. Anthopoulos recalls Herb showing up at his house with his wife’s favorite ice cream during a difficult week; the specific details may have faded, but not the impact of the thoughtfulness and genuine kindness that inspired it, two hallmarks of Herb Solway.