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Thursday, August 07, 2025

REMEMBERING SY GAER


The only thing missing is his little black book. 


 Sy Gaer, a legendary REGJB lawyer, perhaps THE legendary REGJB lawyer, passed away today in 2007.  It’s good that we remember him. As Roy Black, no stranger to legendary status himself told the Wall Street Journal (yeah they reported Sy’s passing!) Sy was a dinosaur from a time when lawyers didn’t run to the prosecutors office to beg for a plea. “He wasn’t afraid to try a case” said Roy, opining that was the greatest compliment you could bestow on a criminal defense attorney.  

For those of you Gen Zers, here is a brief glimpse into Sy’s shtick. 

ASA: We are moving to revoke the defendant’s bond. Since his first case, he’s been arrested and bonded out two more times in the last two weeks. 

Sy: If that isn’t the clearest evidence of police harassment I don’t know what is. 

——-

Sy: I’m here today in court to prevent a tragedy occurring for this poor child. 

Judge : How old is your client ?

Sy: 23 

Judge: Your client is no child. 

Sy: I have suits older than her 

……

We could go on and on. But Sy was no buffoon as generations of young prosecutors found out again and again.  He was sharp in trial and he connected with jurors. He knew the law, believe it or not. True he didn’t take depositions. But he read the FLW every week, although he would never admit it. 

One longtime REGJB lawyer tells the story of when he was an ASA, Sy showing up for a drug trafficking case, “borrowing” a legal pad and proceeding to kick his butt in trial. 

Sy was more than a lawyer or as some would say a caricature of a lawyer.  He was Marine who was in the legendary Korean War battle at the Chosin Reservior.  Like many war veterans, it was not something he ever spoke about.  He also was a published author. He wrote pulp fiction novels in the 1970s. If anyone has one, please please contact us  

Sy had a good heart. He would talk to anyone, give advice when asked, buy  a poor ASA or PD a drink or dinner at the Alibi lounge after work, and throw a struggling defense attorney a case when they needed help. He was a legend in our building and remains in our heart. He was a good man and we miss him most every day we walk into the courthouse. 

Here is the article Susannah Nesmith wrote about Sy when she was a crusading journalist for the Herald. 


34 comments:

Anonymous said...

Sy: “Your Honor, allow me approach the podium while I’m still emotionally able…”

Judge: “Mr. Gaer, have you reviewed the State’s plea offer with your client?”

Sy: “Judge, that was not a plea offer. It was a declaration of war!”

Anonymous said...

In a perfect world, if they ever made a movie about Sy, Walter Matthau would play the role.

Unknown said...

Loved Sy. Loved having drinks with him in the Alibi. I always tried to buy him one. He was so appreciative.
Changing topics. Palantir 52 week low is $26.50. It’s currently 175. Did you miss the train on this one Rumpola?

Unknown said...

I saw him try a case with Shumie. The dynamic duo.

Unknown said...

Sy had an insanity defense. He raised it in voir dire. Jurors were typically hostile saying things like “oh so you want me to let him off on some legal technicality?” Sy was masterful dismantling their hostility and got an NGI verdict on a case where his client chopped his wife’s arm off with a machete. He was a great trial lawyer.

Unknown said...

Sy called me a “sarcastic cynical ensnaring fact-facturing prosecutor” in closing argument and got a not guilty. I bought him a round at the Alibi that night. I loved working in a building that he was in.

Anonymous said...

What a character. I loved the always called me "kid" even though I was in my 60's. One of my favorite Sy Gaer's lines "That's not a plea offer, that a declaration of war". Would love to hear other favorite one liners of his. I also was told that in the 70's when he was in trial, you could hear him screaming in the halls .

Anonymous said...

Legendary.

Anonymous said...

. When I was a pd I averaged 10 trials a year. I tried 16 duis my first year. The new generation of pds average 2 trials a year at most. Sy tried 50 trials a year.

Anonymous said...

He sure was

Anonymous said...

Kudo’s to the Walter Matthau casting. Sy Gaer was my hero. Stunningly generous, hysterically and dryly funny, and the epitome of the totally committed and aggressive advocate. As a novice APD, thrown into my first felony trials—like a deer in headlights—I would follow him from courtroom to courtroom in hopes I could absorb a tiny fraction of his inimitable eviscerating style and wit. He had no files, just his little notebook in which he had a daily list of courtroom appearances written. He never fumbled or skipped a beat in any of his dozens of appearances throughout the courthouse every single day—he just cooly and mostly sarcastically sliced and diced the unwitting ASA’s.

When my law partner and I started private practice in the late 80’s, literally penniless from our APD salaries and law school debt, and with no understanding how to begin, Sy gave us an office in his little building across fromSteve Golembe’s, around the corner from REGB, for peanuts. For those of you who never had the pleasure, his own office had floor to ceiling (really) shag carpeting—I think orange but maybe green—right out of the 60’s. In order for us to pay the first month’s rent, he pitched us a client who simply needed to form a corporation—which we had no idea how to do—telling the guy we were experts, for a fee exactly matching the rent. He then took us step by step through the process. Without Sy, our foray into the private practice would have failed in days, minutes. And he was always there for tips, advice, and a laugh. He was a gem, gone but never forgotten.

Anonymous said...

He tried more cases than anybody I know of. I wonder how many he totaled in his career or if he even kept track.

Anonymous said...

When I was a struggling defense attorney Sy threw some cases at me and helped me get started.

Anonymous said...

I think Sy's greatest trait was his generosity towards other lawyers and willingness to help those in need. Beyond the entertaining schtick was a heart of gold and offering of mentorship to whomever asked. There are plenty of lawyers that are far from team players yet to try a case with Sy meant that you were truly a "team" . From afar he had the schtick but up close he was kind-hearted.

Anonymous said...

Sy was beloved. When he would walk into my court as a young judge I would respectfully always call his case out of turn. He deserved the respect. He ran court to court. He had a list of his cases and often would meet his client for the first time when the case was called. He was loved by many of the best young ASA’s and APD’s. They could never pull off his in court conduct. He always contributed what he could to the judicial campaigns. He was the “Columbo” of the Justice Building. I know Judge Teddy Mastos has some great stories. Sy always said that Ted was his favorite Judge in all his years at our beloved courthouse.

Anonymous said...

By the way Rump - still like SSSS Suro Capital??

Rumpole said...

We are maintaining our $9.25 price target for SSSS shares, which equates to roughly 1x its NAV per share value. We will continue to monitor its portfolio holdings and adjust our thinking for its NAV value per share and our price target accordingly.

We would remind you that our play with SSSS shares is a total return one, which means a combination of stock price appreciation and dividend income. Considering our last pickup was just below $8, should the shares drift back to that level, it would be a nice place to add to our holdings.

During the June quarter, public company exits generated gains of around $21 million, roughly $0.85 per share, but as we know, SuRo’s recent dividend payment amounted to $0.25 per share. On its own, this suggests a continued cadence of dividends, but we should also remember the IPO lockup expiration for CoreWeave shares is mid-September. There is also the expected monetization of SuRo’s Colombier Acquisition Corp II position (2.73% of its portfolio’s assets) as it was combined with GrabAGun on July 15 to form GrabAGun Digital (PEW). Based on those monetizations, we’ll have a better sense of upcoming dividend payments and the potential for SuRo to declare a special dividend late this year, given its business development company status.

Exiting the June quarter, SuRo’s had ~ $52.4 million of liquid assets, including approximately $49.9 million in cash and approximately $2.5 million in unrestricted public securities. Not included in its unrestricted public securities are approximately $40.9 million of public securities subject to lockup or other sales restrictions, which includes its remaining position in CoreWeave. Looking at CoreWeave’s portfolio table, that position has a cost basis of $15.2 billion, which implies a hefty gain, subject to where CRWV shares are trading when the IPO lockup expires.

During the earnings call, management reviewed its larger holdings, which include a position in OpenAI via ARK Type One Deep Ventures Fund LLC shares. Exiting June, that position was SuRo’s second largest behind its remaining CRWV play. OpenAI recently closed a second tranche of its $40 billion financing round at a $300 billion post-money valuation, with indications that tranche was oversubscribed by approximately 5x.

In the last 24 hours, several publications, including the Financial Times, Reuters, Bloomberg, and The Information, have reported that OpenAI is now in discussions to conduct a secondary sale at a valuation of $500 billion. If completed, it would lead to another markup of SuRo’s OpenAI position, which stood at $27.8 million exiting June compared to its $17.7 million cost basis. That would help give some lift to SuRo’s NAV per share.

So yeah. We still like it ALOT

Anonymous said...

Thanks for posting this remembrance. An REG original. So many have tried to emulate him but no one could do it the way Sy did it. I always wanted to try to practice like Sy but frankly could never get up the nerves.

Anonymous said...

Judge: Mr Gaer a good friend of mine told me he was sitting at a table next to yours at lunch yesterday and heard you say I was a filthy son of a bitch. Sy: I don’t think I was that generous

Anonymous said...

New Leadership at the SAO administration is running it to the grow

Anonymous said...

I ran him on newspapers.com once, and to read the stories about him from back in the day were something else. And I mean the 60s!

Anonymous said...

Did you know that in 1968, Sy was the Belle Glade field agent for South Florida Migrant Legal Services

Theodore Mastos said...

There will never be another Sy Gaer. It is amusing to read the funny anecdotes from Sy's experiences in our REG building. Unfortunately, the number of lawyers who battled in court with Sy are diminishing, as he has been gone since 2007.
Those who did try cases with Sy became battle tested warriors. He would beat you before you could realize what had happened. Then he would smile and say," you did ok kid." He never gloated over an acquittal.

He had that kind of a "Humphrey Bogart" edge to him, although I may have lost the audience with that analogy. But once you cracked that veneer you had a friend for life.
Next time you are in a saloon just hoist one for Sy. May his memory live on forever.

CAPTAIN JUSTICE said...

JIM LOVELL HAS PASSED AWAY .....

Apollo 13 Commander James Lovell, Jr. passed away at the age of 97. Most famous for leading the three man crew that survived a near catastrophic explosion in space in 1970, he was later immortalized by Tom Hanks in the movie "Apollo 13".

Cap Out .....
Captain4Justice@gmail.com

Anonymous said...

Looking forward to Rumpole’ Lovell remembrance.

Unknown said...

“As first reported on the anonymous justice building blog, a mysterious cabal of current and former judges who call themselves “the collective “ have been meeting secretly in small dark bars in Wynwood after court once or twice a week to coordinate opposition to the current judicial administration.” As one judge muttered “we are not going to let a bunch of MAGA yahoos destroy the Miami courts the way Bondi has destroyed the DOJ or Patel has tanked the FBI.” More to come. Long live the collective. Fight the power Rump ✊

Rumpole said...

Correction. I reported nothing about this.

Anonymous said...

Best place for a steak dinner in Boca ? Abe and Louie’s hands down Rump.

Anonymous said...

The Collective is being whispered about in the far corners of the REBJB hallways. Not sure if it was true but here we are.

Anonymous said...

I respectfully disagree - New York Prime

Anonymous said...

No one in their right mind goes to Boca.

Anonymous said...

Anytime I say Sy in line (of defense attorneys waiting to be heard) I knew it was going to be a good morning

Anonymous said...

Sy was like an old character out of a good legal novel. Defense attorneys wanted to win like him and prosecutors wanted to beat him. I loved to see him going floor to floor in the Justice Building as he did his schtick.

Anonymous said...

One of the hardest working attys ever—Often trying 2 cases simultaneously via morning and afternoon back up. I can hear him now, “Carol dahling, how are you, kid, my young client deserves a break. You look sympathetic today.” His client: a 60 yr old 5x HVO. Fun times. Miss him so much.