WEBVTT 00:00:00.000 --> 00:00:03.120 Welcome to the Deep Dive. We are taking a look 00:00:03.120 --> 00:00:08.439 today at a story that operates as equal parts 00:00:08.439 --> 00:00:11.419 political thriller, historical comedy, and just 00:00:11.419 --> 00:00:14.560 a masterclass in pure unadulterated hustle. Yeah, 00:00:14.580 --> 00:00:16.000 I mean, it's one of those historical narratives 00:00:16.000 --> 00:00:19.339 that feels almost too cinematic to be real, you 00:00:19.339 --> 00:00:22.339 know, yet it shaped the very foundations of the 00:00:22.339 --> 00:00:24.460 country's largest city. Right. And our mission 00:00:24.460 --> 00:00:26.640 for you today is to extract a roadmap of how 00:00:26.640 --> 00:00:29.600 power is actually built, how it's lost, and how 00:00:29.600 --> 00:00:31.699 it is ultimately remembered in a major metropolis. 00:00:31.920 --> 00:00:35.000 Exactly. We are basing this deep dive on a single, 00:00:35.179 --> 00:00:37.740 incredibly dense source. It's a comprehensive 00:00:37.740 --> 00:00:40.780 Wikipedia article detailing the life of John 00:00:40.780 --> 00:00:43.259 Francis Hyland. The 97th mayor of New York City. 00:00:43.479 --> 00:00:45.899 Yep, the 97th and the 7th since the consolidation 00:00:45.899 --> 00:00:48.520 of the five boroughs. But we aren't just reading 00:00:48.520 --> 00:00:50.560 you a dusty biography today. We're looking at 00:00:50.560 --> 00:00:56.020 the mechanics of political machines. Oh, very 00:00:56.020 --> 00:00:59.200 dramatic. Right. And a man who went toe -to -toe 00:00:59.200 --> 00:01:01.299 with the intellectual elite of his day. Okay, 00:01:01.380 --> 00:01:03.780 let's unpack this. Before he was the mayor, before 00:01:03.780 --> 00:01:06.420 he was a judge, he was known simply as Red Mike. 00:01:06.640 --> 00:01:10.060 Red Mike, which paints a picture of a scrappy 00:01:10.060 --> 00:01:12.620 fighter, which is a pretty accurate baseline 00:01:12.620 --> 00:01:14.760 for understanding him. For sure. He was a man 00:01:14.760 --> 00:01:17.569 who started with absolutely nothing. took on 00:01:17.569 --> 00:01:20.269 what he called the interests, and left a legacy 00:01:20.269 --> 00:01:22.989 tangled in monumental infrastructure projects 00:01:22.989 --> 00:01:26.030 and, well, really cruel political punchlines. 00:01:26.250 --> 00:01:28.150 If you look at his origins in the Catskill Mountains 00:01:28.150 --> 00:01:31.290 around 1868, it's the classic immigrant grit 00:01:31.290 --> 00:01:34.349 story. But I really want to understand the scale 00:01:34.349 --> 00:01:36.930 of it. How does a kid from Hunter, New York, 00:01:37.069 --> 00:01:40.329 with barely any resources, even begin a trajectory 00:01:40.329 --> 00:01:42.510 towards City Hall? You really have to look at 00:01:42.510 --> 00:01:44.849 the sheer economic anxiety that defined his youth. 00:01:45.200 --> 00:01:47.140 His father was an Irish immigrant from County 00:01:47.140 --> 00:01:49.579 Cabin who came over at age seven. Right. And 00:01:49.579 --> 00:01:51.239 the father actually ended up fighting in the 00:01:51.239 --> 00:01:53.939 Civil War as a corporal in the 120th New York 00:01:53.939 --> 00:01:56.159 Infantry. Which was known as the Ulster Regiment, 00:01:56.180 --> 00:01:58.439 right? Exactly. The Ulster Regiment. And his 00:01:58.439 --> 00:02:01.079 mother, conversely, had these deep American roots. 00:02:01.420 --> 00:02:03.920 Her grandfather fought in the American Revolution 00:02:03.920 --> 00:02:07.319 alongside Lafayette. Wow. So there's this intense 00:02:07.319 --> 00:02:10.300 blend of immigrant hustle and patriotic legacy 00:02:10.300 --> 00:02:13.479 right from the start. Definitely. But despite 00:02:13.479 --> 00:02:17.080 that heritage. The family was dirt poor. I mean, 00:02:17.080 --> 00:02:19.300 they were strapped to a 60 -acre farm with a 00:02:19.300 --> 00:02:22.879 $1 ,500 mortgage. Which in the 1870s and 80s 00:02:22.879 --> 00:02:25.620 was a massive financial weight to carry. A crushing 00:02:25.620 --> 00:02:28.080 weight. They struggled just to pay the semiannual 00:02:28.080 --> 00:02:31.479 interest on it. As the oldest boy of five children, 00:02:31.759 --> 00:02:35.219 Hyland's life was consumed by farm labor using 00:02:35.219 --> 00:02:37.879 primitive hand tools. Just back -breaking stuff. 00:02:38.340 --> 00:02:40.360 Yeah, and education was treated as a distant 00:02:40.360 --> 00:02:43.979 luxury. The local school district was so impoverished 00:02:43.979 --> 00:02:46.699 that only one family could afford the required 00:02:46.699 --> 00:02:49.340 grammar or history book. Wait, one family in 00:02:49.340 --> 00:02:51.719 the whole district? One family. Hyland had to 00:02:51.719 --> 00:02:54.159 borrow this single book just to learn. He was 00:02:54.159 --> 00:02:56.240 only getting about four to five hours of schooling 00:02:56.240 --> 00:02:59.000 a day for just five months out of the year. Because 00:02:59.000 --> 00:03:01.199 the farm demanded the rest of his time. Right. 00:03:01.280 --> 00:03:03.460 And he was already doing side hustles as a teenager, 00:03:03.719 --> 00:03:05.860 wasn't he? The source mentions him working on 00:03:05.860 --> 00:03:08.060 a local railroad before he ever left the mountains. 00:03:08.360 --> 00:03:11.439 He was. Every spring, he'd go work for the Catskill 00:03:11.439 --> 00:03:13.900 Railroad. He was literally digging earth and 00:03:13.900 --> 00:03:16.080 tamping it beneath the tracks to stabilize them 00:03:16.080 --> 00:03:18.180 after the winter freezes. It's just raw manual 00:03:18.180 --> 00:03:21.199 labor. Exactly. And sending every penny back 00:03:21.199 --> 00:03:23.360 to help his parents pay that mortgage interest. 00:03:23.840 --> 00:03:26.939 But by the winter of 1887, when he's 19 years 00:03:26.939 --> 00:03:30.000 old, he realizes the math just isn't working 00:03:30.000 --> 00:03:32.340 out. The farm just wasn't making enough. No. 00:03:32.650 --> 00:03:34.490 So he figures he can make more money for the 00:03:34.490 --> 00:03:36.889 family if he heads downstate. So he leaves the 00:03:36.889 --> 00:03:39.930 Catskills and heads to Brooklyn. But I read he 00:03:39.930 --> 00:03:43.650 only had something like $3 to his name. How does 00:03:43.650 --> 00:03:46.590 a teenager with no money and a grade school education 00:03:46.590 --> 00:03:49.610 even get a foot in the door in 1880s New York? 00:03:50.060 --> 00:03:53.080 Well, he left the mountains with exactly $3 .50 00:03:53.080 --> 00:03:55.860 in his pocket. Incredible. He spends $2 on a 00:03:55.860 --> 00:03:58.259 train ticket, walks across the Brooklyn Bridge, 00:03:58.419 --> 00:04:00.460 and immediately starts looking for leverage. 00:04:00.639 --> 00:04:02.439 Just hits the ground running. The very first 00:04:02.439 --> 00:04:04.620 day he arrives, he sees construction happening 00:04:04.620 --> 00:04:08.039 on an elevated railroad. Having never even seen 00:04:08.039 --> 00:04:10.840 an elevated structure before, he literally climbs 00:04:10.840 --> 00:04:13.159 up onto the tracks, tracks down the foreman, 00:04:13.240 --> 00:04:15.900 and leverages his brief manual labor experience 00:04:15.900 --> 00:04:19.180 on the Catskill Railroad to ask for a job. Just 00:04:19.180 --> 00:04:21.220 walking up and demanding a job, that takes some 00:04:21.220 --> 00:04:24.259 serious nerve. It does. And the foreman tells 00:04:24.259 --> 00:04:27.100 him to show up the next day to lay rails. But 00:04:27.100 --> 00:04:29.439 he doesn't stop at laying rails. Our source notes 00:04:29.439 --> 00:04:31.920 he actively campaigned for a promotion almost 00:04:31.920 --> 00:04:34.660 immediately. Oh, he was relentless. He went to 00:04:34.660 --> 00:04:37.079 the office of the manager of the Brooklyn Union 00:04:37.079 --> 00:04:40.040 Elevated Railroad every single day. Every single 00:04:40.040 --> 00:04:43.100 day. Every day. He badgered the management until 00:04:43.100 --> 00:04:45.319 they finally gave him an interview and promoted 00:04:45.319 --> 00:04:48.540 him to a fireman, which involved incredibly heavy 00:04:48.540 --> 00:04:52.019 labor for $1 .50 a day. Still pretty low wages. 00:04:52.240 --> 00:04:54.980 Yeah, but here is the crazy part. The timing 00:04:54.980 --> 00:04:57.939 of this is legendary. His first day reporting 00:04:57.939 --> 00:05:00.600 to the East New York station as a fireman was 00:05:00.600 --> 00:05:04.920 March 11, 1888. Oh, wow. That is the exact day 00:05:04.920 --> 00:05:07.180 of the Great Blizzard. The Blizzard of 88. That 00:05:07.180 --> 00:05:09.360 was one of the most severe snowstorms in American 00:05:09.360 --> 00:05:11.879 history. Starting a grueling outdoor physical 00:05:11.879 --> 00:05:14.560 labor job on that specific day is wild. And he 00:05:14.560 --> 00:05:17.139 pushed through it. After two years of being a 00:05:17.139 --> 00:05:20.019 stoker and an engine hustler, he passed a test 00:05:20.019 --> 00:05:22.899 and became a locomotive engineer, making $3 .50 00:05:22.899 --> 00:05:25.970 a day. Which was a big step up. It was, but it 00:05:25.970 --> 00:05:28.790 required brutal hours. We're talking 13 hour 00:05:28.790 --> 00:05:32.269 runs on weekdays, 12 hours on Saturdays and 11 00:05:32.269 --> 00:05:34.970 hours on Sundays. What's fascinating here is 00:05:34.970 --> 00:05:38.490 how he utilized that time. He wasn't just surviving 00:05:38.490 --> 00:05:42.139 that 13 hour a day grind. He was incredibly systematic 00:05:42.139 --> 00:05:45.180 about his financial goals. Very systematic. While 00:05:45.180 --> 00:05:48.120 working as a motorman, he regularly made the 00:05:48.120 --> 00:05:51.319 $75 semi -annual interest payments for his family's 00:05:51.319 --> 00:05:53.860 farm back upstate. Yeah. And he actually managed 00:05:53.860 --> 00:05:56.420 to pay off the entire principal before he ever 00:05:56.420 --> 00:05:58.540 left the railroad job. It's a huge accomplishment. 00:05:58.720 --> 00:06:01.399 He even went back to Hunter, married his childhood 00:06:01.399 --> 00:06:03.759 sweetheart, Marion O 'Hara, and moved her to 00:06:03.759 --> 00:06:06.459 Bushwick in Brooklyn. He later wrote that once 00:06:06.459 --> 00:06:09.620 he was making $100 a month, he had zero inclination 00:06:09.620 --> 00:06:12.300 to seek any other position. He thought he had 00:06:12.300 --> 00:06:14.819 made it. He had achieved his version of the American 00:06:14.819 --> 00:06:18.839 dream. But then a tragedy completely altered 00:06:18.839 --> 00:06:21.240 his trajectory. Right. His younger brother, who 00:06:21.240 --> 00:06:23.259 was studying law and upon whom the family had 00:06:23.259 --> 00:06:25.720 pinned all their hopes for upward mobility, passed 00:06:25.720 --> 00:06:29.009 away. That's devastating. It was. And that loss 00:06:29.009 --> 00:06:32.350 became the catalyst for Hyland to pursue a career 00:06:32.350 --> 00:06:35.449 in law himself, basically to pick up the mantle 00:06:35.449 --> 00:06:38.290 for his family. But remember, he barely had a 00:06:38.290 --> 00:06:41.329 grade school education. To pivot to law, he had 00:06:41.329 --> 00:06:43.269 to do massive amounts of catch up. He had to 00:06:43.269 --> 00:06:45.529 go to the Long Island Business College just to 00:06:45.529 --> 00:06:47.750 prepare for the regents exams. Right. For those 00:06:47.750 --> 00:06:49.589 of you listening who might not be familiar with 00:06:49.589 --> 00:06:52.529 the New York education system of that era, the 00:06:52.529 --> 00:06:54.810 regents exams were the standardized state tests 00:06:54.810 --> 00:06:57.389 required to prove high school level competency. 00:06:57.670 --> 00:06:59.589 You couldn't just walk into a law school without 00:06:59.589 --> 00:07:01.589 passing them. And he needed a lot of help to 00:07:01.589 --> 00:07:03.889 get there. He had a teacher who actually gave 00:07:03.889 --> 00:07:06.250 up his lunch hours to help highlight. and study 00:07:06.250 --> 00:07:08.550 for those exams. Which is such a great detail. 00:07:08.810 --> 00:07:11.389 It is. And as a quick aside, it became a great 00:07:11.389 --> 00:07:14.290 example of political loyalty later on. When Hyland 00:07:14.290 --> 00:07:16.730 eventually became mayor, he rewarded that exact 00:07:16.730 --> 00:07:19.430 teacher with a comfortable city job in the Department 00:07:19.430 --> 00:07:22.589 of Water Supply. Gotta reward your base. So once 00:07:22.589 --> 00:07:25.310 he passes the regents exams, he enrolls in New 00:07:25.310 --> 00:07:28.870 York Law School. And there is an incredible historical 00:07:28.870 --> 00:07:32.930 detail hidden in his time there. One of his professors 00:07:32.930 --> 00:07:35.930 for constitutional law was none other than Woodrow 00:07:35.930 --> 00:07:38.870 Wilson. It's almost hard to believe. The future 00:07:38.870 --> 00:07:40.870 mayor of New York being taught by the future 00:07:40.870 --> 00:07:43.449 president of the United States. It really highlights 00:07:43.449 --> 00:07:45.930 how concentrated the circles of influence were 00:07:45.930 --> 00:07:48.709 becoming, even for a guy who started out tamping 00:07:48.709 --> 00:07:50.670 dirt under railroad ties. But here's where it 00:07:50.670 --> 00:07:53.029 gets really interesting. Hyland graduates in 00:07:53.029 --> 00:07:56.370 October 1897 and clerks for a Long Island city 00:07:56.370 --> 00:07:59.730 attorney. He's ready to take the bar exam, but 00:07:59.730 --> 00:08:02.009 the earliest one available is all the way up 00:08:02.009 --> 00:08:04.149 in Syracuse. Yeah, nowhere near Brooklyn. Right 00:08:04.149 --> 00:08:06.110 before he's supposed to go, he gets into a near 00:08:06.110 --> 00:08:08.649 accident with a railroad supervisor. Hyland claims 00:08:08.649 --> 00:08:10.790 it was the supervisor's fault, but he gets fired 00:08:10.790 --> 00:08:13.310 from the railroad anyway. Typical. So he's out 00:08:13.310 --> 00:08:15.649 of a job, he needs to get to Syracuse, and he's 00:08:15.649 --> 00:08:18.639 tight on cash. What does he do? He brilliantly 00:08:18.639 --> 00:08:20.899 uses his membership pass from the Brotherhood 00:08:20.899 --> 00:08:23.420 of Locomotive Engineers to travel the rails for 00:08:23.420 --> 00:08:27.240 free up to Syracuse. He takes the exam and he 00:08:27.240 --> 00:08:29.839 passes. Passing the bar is only step one, though. 00:08:30.240 --> 00:08:32.899 He quickly realized that starting a law practice 00:08:32.899 --> 00:08:35.840 required upfront capital, something he no longer 00:08:35.840 --> 00:08:38.740 had without his railroad salary. So what's his 00:08:38.740 --> 00:08:42.039 move? Well, in a massive gamble, he mortgages 00:08:42.039 --> 00:08:44.080 the family farm back in the Catskills again. 00:08:44.299 --> 00:08:46.340 Oh man, after spending all those years paying 00:08:46.340 --> 00:08:49.320 it off. Exactly. This time he mortgages it for 00:08:49.320 --> 00:08:52.299 $500 to open an office on the corner of Gates 00:08:52.299 --> 00:08:55.139 Avenue and Broadway in Bushwick. And he forms 00:08:55.139 --> 00:08:57.299 a partnership with an attorney named Harry C. 00:08:57.480 --> 00:09:00.179 Underhill. Underhill did the office work and 00:09:00.179 --> 00:09:02.720 wrote legal treatises while Hyland became the 00:09:02.720 --> 00:09:06.379 trial lawyer. Iredi only made $24 his first month, 00:09:06.460 --> 00:09:09.730 taking on small civil cases and family law. Slow 00:09:09.730 --> 00:09:12.870 start. Yeah, but he was highly strategic about 00:09:12.870 --> 00:09:14.809 the cases he took. He wasn't trying to mingle 00:09:14.809 --> 00:09:16.649 with corporate titans. He knew his power base 00:09:16.649 --> 00:09:19.149 was the working class of Brooklyn. He took on 00:09:19.149 --> 00:09:21.850 cases that mattered to everyday commuters. His 00:09:21.850 --> 00:09:24.269 firm famously won a ruling that forced the Brooklyn 00:09:24.269 --> 00:09:26.809 Heights Railroad Company to offer free transfers 00:09:26.809 --> 00:09:29.129 at all junctions. That's huge. It might sound 00:09:29.129 --> 00:09:32.070 like a minor administrative victory today, but 00:09:32.070 --> 00:09:34.190 for a working class family in Brooklyn at the 00:09:34.190 --> 00:09:36.870 turn of the century, a second transit fare could 00:09:36.870 --> 00:09:39.070 literally break the weekly budget. Absolutely. 00:09:39.309 --> 00:09:42.690 Winning that case got him incredible local publicity 00:09:42.690 --> 00:09:46.029 and really solidified his reputation as a champion 00:09:46.029 --> 00:09:48.929 of the common writer. Alongside his legal work, 00:09:49.149 --> 00:09:52.590 he was relentlessly networking. He kept his union 00:09:52.590 --> 00:09:55.269 membership active, joined the Foresters of America, 00:09:55.490 --> 00:09:58.090 the Broadway Board of Trade, the Local Taxpayer 00:09:58.090 --> 00:10:00.309 Association, and began working his way up the 00:10:00.309 --> 00:10:02.330 local Democratic club. Just shaking every hand 00:10:02.330 --> 00:10:04.509 he could. And some of that networking was purely 00:10:04.509 --> 00:10:07.580 accidental. Our source highlights how Hyland 00:10:07.580 --> 00:10:10.200 met John H. McCooey, who would eventually become 00:10:10.200 --> 00:10:12.879 the immensely powerful Brooklyn Democratic Party 00:10:12.879 --> 00:10:15.240 boss. Right. They didn't meet at a fancy political 00:10:15.240 --> 00:10:17.679 gala. No, they met at the local post office. 00:10:17.799 --> 00:10:20.200 McCooey was a postal clerk at the time, and Hyland 00:10:20.200 --> 00:10:22.440 was just there sending money orders to his parents 00:10:22.440 --> 00:10:24.700 to pay the interest on that new farm mortgage. 00:10:25.100 --> 00:10:28.019 It's such a small world. McCooey showed him some 00:10:28.019 --> 00:10:30.419 kindness regarding the paperwork. Hyland remembered 00:10:30.419 --> 00:10:33.769 it, and they became lifelong friends. That is 00:10:33.769 --> 00:10:36.009 a vital lesson for anyone navigating their own 00:10:36.009 --> 00:10:38.590 career. Sometimes the most pivotal connections 00:10:38.590 --> 00:10:41.470 happen during the most mundane errands. You never 00:10:41.470 --> 00:10:43.350 know who the clerk across the counter is going 00:10:43.350 --> 00:10:46.370 to become in 20 years. It's so true. All of this 00:10:46.370 --> 00:10:48.909 local groundwork pays off when Highland emerges 00:10:48.909 --> 00:10:52.169 from obscurity during the wild citywide elections 00:10:52.169 --> 00:10:55.470 of 1903. This is where we get into the heavy 00:10:55.470 --> 00:10:58.230 machinery of Tammany Hall politics. Oh, yeah. 00:10:58.309 --> 00:11:01.129 The 1903 election was a chaotic internal power 00:11:01.129 --> 00:11:04.220 struggle. For those who might need a refresher, 00:11:04.340 --> 00:11:07.379 Tammany Hall was the formidable democratic political 00:11:07.379 --> 00:11:09.919 machine that basically controlled New York politics 00:11:09.919 --> 00:11:12.620 through a deeply entrenched system of patronage. 00:11:12.779 --> 00:11:15.379 Meaning they handed out city jobs and contracts 00:11:15.379 --> 00:11:18.259 to loyal supporters to maintain power. Exactly. 00:11:18.360 --> 00:11:20.519 In Manhattan, Charles Francis Murphy had just 00:11:20.519 --> 00:11:22.179 taken over as the head of the Tammany machine. 00:11:22.379 --> 00:11:24.720 Murphy was a guy who got rich leasing city docks 00:11:24.720 --> 00:11:26.639 to shipping companies, and his grand ambition 00:11:26.639 --> 00:11:29.080 was to extend Tammany's influence out of Manhattan 00:11:29.080 --> 00:11:31.929 and into all the outer boroughs. particularly 00:11:31.929 --> 00:11:34.950 Brooklyn. To do this, Murphy decided to run George 00:11:34.950 --> 00:11:38.190 B. McClellan Jr. for mayor, trying to dislodge 00:11:38.190 --> 00:11:40.970 the current fusionist mayor. Right. And just 00:11:40.970 --> 00:11:44.149 to clarify, a fusionist mayor was basically a 00:11:44.149 --> 00:11:47.169 coalition candidate. Republicans and independent 00:11:47.169 --> 00:11:50.129 Democrats teaming up specifically to keep the 00:11:50.129 --> 00:11:52.250 Tammany Hall political machine out of power. 00:11:52.509 --> 00:11:55.330 But the Brooklyn political leaders, headed by 00:11:55.330 --> 00:11:58.529 a boss named Hugh McLaughlin, absolutely hated 00:11:58.529 --> 00:12:01.429 Murphy's move. They felt McClellan would ruin 00:12:01.429 --> 00:12:03.509 the down ticket raises in Brooklyn and cost them 00:12:03.509 --> 00:12:05.669 local offices like the district attorney. You 00:12:05.669 --> 00:12:08.610 saw right through it. Yeah. Many suspected Murphy 00:12:08.610 --> 00:12:10.850 was doing this on purpose to cut off Brooklyn's 00:12:10.850 --> 00:12:13.409 independent patronage base. It all came to a 00:12:13.409 --> 00:12:15.330 head at the Democratic Convention on October 00:12:15.330 --> 00:12:18.570 1st, 1903 at Carnegie Hall. It sounded like an 00:12:18.570 --> 00:12:21.129 absolute madhouse. It was. Brooklyn Assistant 00:12:21.129 --> 00:12:23.769 District Attorney Martin W. Littleton stood up, 00:12:23.850 --> 00:12:26.629 looked directly at Murphy, and delivered a blistering 00:12:26.629 --> 00:12:29.529 speech screaming about Tammany treachery. There 00:12:29.529 --> 00:12:32.009 was wild applause, shouts of traitor, and massive 00:12:32.009 --> 00:12:34.549 behind -the -scenes scheming to run an anti -Tammany 00:12:34.549 --> 00:12:37.659 ticket. But Murphy just sat there, smiling through 00:12:37.659 --> 00:12:40.039 the abuse, knowing he had the delegate math. 00:12:41.019 --> 00:12:43.659 Tammany forced their slate through anyway. The 00:12:43.659 --> 00:12:46.220 Brooklyn opposition collapsed, and in the resulting 00:12:46.220 --> 00:12:49.159 turmoil, the old Brooklyn boss McLaughlin was 00:12:49.159 --> 00:12:52.240 ousted by his own subordinate. This is the crucial 00:12:52.240 --> 00:12:54.460 turning point for Highland. Instead of getting 00:12:54.460 --> 00:12:56.419 swept away in the collapse of the old Brooklyn 00:12:56.419 --> 00:12:59.240 guard, he aligned himself perfectly with the 00:12:59.240 --> 00:13:01.509 new power structure. He knew which way the wind 00:13:01.509 --> 00:13:03.830 was blowing. Because he had built such a solid 00:13:03.830 --> 00:13:06.450 reputation among the working class and had those 00:13:06.450 --> 00:13:08.970 connections with guys like McCooey, the new party 00:13:08.970 --> 00:13:13.149 bosses saw him as a useful asset. In 1906, they 00:13:13.149 --> 00:13:15.320 got him appointed as a city magistrate. Which 00:13:15.320 --> 00:13:18.120 bridges a massive gap in his story. He didn't 00:13:18.120 --> 00:13:20.299 just jump from a convention floor to the mayor's 00:13:20.299 --> 00:13:22.759 office. He spent the next decade working as a 00:13:22.759 --> 00:13:25.500 magistrate and later a county court judge, constantly 00:13:25.500 --> 00:13:27.759 ruling in ways that favored his working class 00:13:27.759 --> 00:13:30.580 base. He really used that time on the bench to 00:13:30.580 --> 00:13:33.039 endear himself to powerful allies, particularly 00:13:33.039 --> 00:13:35.340 the newspaper publisher William Randolph Hearst. 00:13:35.419 --> 00:13:38.399 Hearst loved Hyland's anti -monopoly rhetoric. 00:13:38.720 --> 00:13:42.700 He did. By 1917, Tammany Hall and Hearst needed 00:13:42.700 --> 00:13:46.000 a reliable, populist candidate for mayor to take 00:13:46.000 --> 00:13:49.120 back the city from reformers. Island was their 00:13:49.120 --> 00:13:52.100 guy. He defeated the incumbent and won the mayoralty, 00:13:52.240 --> 00:13:54.620 notably becoming the first Democratic candidate 00:13:54.620 --> 00:13:57.059 to capture a significant portion of the African 00:13:57.059 --> 00:13:59.919 -American vote. Once in office, he had a very 00:13:59.919 --> 00:14:03.159 singular obsession for this way. Having been 00:14:03.159 --> 00:14:05.360 a motorman himself, he understood that transit 00:14:05.360 --> 00:14:07.860 costs disproportionately impacted the working 00:14:07.860 --> 00:14:10.539 class. He was absolutely determined to keep it 00:14:10.539 --> 00:14:13.120 strictly at five cents. To bypass the corporate 00:14:13.120 --> 00:14:15.299 monopolies that ran the trains at the time, the 00:14:15.299 --> 00:14:18.559 IRT and the BMT Highland set in motion the building 00:14:18.559 --> 00:14:21.220 of the Independent Subway System, or the IND. 00:14:21.279 --> 00:14:23.730 Right. It was designed to be entirely city -owned 00:14:23.730 --> 00:14:26.409 and operated, competing directly with the private 00:14:26.409 --> 00:14:29.690 lines to force them to keep fares low. That system 00:14:29.690 --> 00:14:31.909 eventually became a massive chunk of the modern 00:14:31.909 --> 00:14:33.929 New York City subway we know today. His fight 00:14:33.929 --> 00:14:35.710 against the corporate monopolies wasn't quiet 00:14:35.710 --> 00:14:39.450 either. In 1922, while sitting as mayor, he delivered 00:14:39.450 --> 00:14:42.350 a highly publicized fiery speech attacking what 00:14:42.350 --> 00:14:44.490 he called the invisible government. Yeah, that 00:14:44.490 --> 00:14:47.500 speech is infamous. He described it as a giant 00:14:47.500 --> 00:14:50.639 octopus sprawling its slimy legs over the nation. 00:14:51.019 --> 00:14:54.159 He specifically called out the Rockefeller Standard 00:14:54.159 --> 00:14:56.899 Oil interests and a small group of international 00:14:56.899 --> 00:14:59.639 bankers claiming they control the majority of 00:14:59.639 --> 00:15:02.539 newspapers, dictated who got nominated for public 00:15:02.539 --> 00:15:05.259 office and virtually ran the U .S. government 00:15:05.259 --> 00:15:07.879 for their own selfish purposes. And it's really 00:15:07.879 --> 00:15:09.639 important to note for you listening that our 00:15:09.639 --> 00:15:12.960 goal here isn't to endorse these 1920s conspiracy 00:15:12.960 --> 00:15:15.350 theories. Absolutely not. We are. absolutely 00:15:15.350 --> 00:15:17.850 not taking sides on his populist rhetoric or 00:15:17.850 --> 00:15:19.850 saying he was right about this giant octopus. 00:15:20.149 --> 00:15:21.750 Right. We are just looking at the historical 00:15:21.750 --> 00:15:25.009 reality of how politicians of this era utilize 00:15:25.009 --> 00:15:27.950 this kind of language to rally their base against 00:15:27.950 --> 00:15:30.809 perceived elite control. Exactly. We are impartially 00:15:30.809 --> 00:15:32.929 looking at the mechanics of his messaging. And 00:15:32.929 --> 00:15:34.929 if we connect this to the bigger picture, the 00:15:34.929 --> 00:15:37.070 mechanics of that messaging were rooted in very 00:15:37.070 --> 00:15:39.950 deep -seated post -Gilded Age anxieties. The 00:15:39.950 --> 00:15:42.570 wealth gap was staggering. The country had just 00:15:42.570 --> 00:15:44.950 watched massive industrial concentration create 00:15:44.950 --> 00:15:48.389 unprecedented wealth for a few, while heavily 00:15:48.389 --> 00:15:52.049 impoverishing the working poor. Hyland, a man 00:15:52.049 --> 00:15:54.590 who literally shoveled coal in a blizzard to 00:15:54.590 --> 00:15:57.529 pay off a farm mortgage, was channeling the very 00:15:57.529 --> 00:16:00.870 real anger of his constituents. But that constant 00:16:00.870 --> 00:16:03.730 battling against the elites had a dark side for 00:16:03.730 --> 00:16:06.460 his legacy. Despite his massive political power, 00:16:06.740 --> 00:16:09.240 he was never respected by the intellectual or 00:16:09.240 --> 00:16:12.059 political upper crust. They didn't consider him 00:16:12.059 --> 00:16:14.600 highly intelligent or articulate. He was viewed 00:16:14.600 --> 00:16:17.279 as a bit of a populist brute. His political opponents 00:16:17.279 --> 00:16:20.139 actively worked to craft a narrative that he 00:16:20.139 --> 00:16:22.820 was a buffoon. Because he wasn't a polished orator, 00:16:22.940 --> 00:16:25.539 he was an easy target for the media and the political 00:16:25.539 --> 00:16:28.500 operatives of the time, who delighted in mocking 00:16:28.500 --> 00:16:31.240 him. Which brings us to one of the most painfully 00:16:31.240 --> 00:16:33.779 funny anecdotes in the source material. According 00:16:33.779 --> 00:16:36.000 to the legendary urban planner Robert Moses, 00:16:36.360 --> 00:16:38.700 Hyland went through almost an entire mayoral 00:16:38.700 --> 00:16:41.620 campaign using just one single stump speech, 00:16:41.840 --> 00:16:44.419 his call, to keep the five -cent subway fare. 00:16:44.559 --> 00:16:47.019 Just hammering that one point. Right. And he 00:16:47.019 --> 00:16:48.940 eventually asked Moses to help him write a new 00:16:48.940 --> 00:16:51.779 speech. Moses obliges and writes him a fresh 00:16:51.779 --> 00:16:54.399 one. The first time Hyland tries to deliver it, 00:16:54.480 --> 00:16:56.799 he reaches the dramatic climax. He's supposed 00:16:56.799 --> 00:16:59.580 to invoke the Revolutionary War, a subject close 00:16:59.580 --> 00:17:01.559 to his heart, given his grandfather's service. 00:17:01.740 --> 00:17:04.220 Right. The line on the page is, I call for the 00:17:04.220 --> 00:17:08.480 spirit of 1776. But Hyland completely misses 00:17:08.480 --> 00:17:11.259 the historical context. He looks at the paper 00:17:11.259 --> 00:17:13.299 and reads out the numbers individually, yelling 00:17:13.299 --> 00:17:15.660 to the crowd, I call for the spirit. Spirit of 00:17:15.660 --> 00:17:20.930 1776. Ouch. It's a devastating gaffe. And it's 00:17:20.930 --> 00:17:23.589 exactly the kind of story that the elites circulated 00:17:23.589 --> 00:17:26.109 to undermine his credibility. But it wasn't just 00:17:26.109 --> 00:17:28.650 bad speeches that led to his downfall. By the 00:17:28.650 --> 00:17:31.150 end of his second term, an investigative committee 00:17:31.150 --> 00:17:34.029 appointed by Governor Al Smith severely criticized 00:17:34.029 --> 00:17:36.089 his handling of the subway system. Wait, hold 00:17:36.089 --> 00:17:38.049 on. If he was this champion of the working class 00:17:38.049 --> 00:17:40.150 commuter, why was the governor's committee criticizing 00:17:40.150 --> 00:17:42.910 his transit management? Was he actually mismanaging 00:17:42.910 --> 00:17:45.329 it or was this just political sabotage from Al 00:17:45.329 --> 00:17:48.470 Smith's camp? Well, it's a mix of both. His stubbornness 00:17:48.470 --> 00:17:50.549 on the five cent fare meant the private transit 00:17:50.549 --> 00:17:53.430 companies were starving for capital because they 00:17:53.430 --> 00:17:55.690 couldn't raise fares to meet inflation. They 00:17:55.690 --> 00:17:57.630 couldn't afford to maintain the lines or build 00:17:57.630 --> 00:17:59.769 new ones fast enough to keep up with population 00:17:59.769 --> 00:18:02.710 growth. So the system was falling apart. The 00:18:02.710 --> 00:18:06.750 result was massive, dangerous overcrowding. Governor 00:18:06.750 --> 00:18:09.259 Al Smith. who was also a Tammany Democrat but 00:18:09.259 --> 00:18:12.299 aligned with a different faction, used this gridlock 00:18:12.299 --> 00:18:14.880 as leverage to argue Hyland was ineffective. 00:18:15.279 --> 00:18:17.440 So Tammany Hall, the very machine that helped 00:18:17.440 --> 00:18:20.859 install him, turns on him. In 1925, they ran 00:18:20.859 --> 00:18:23.839 the slick, highly charismatic state senator Jimmy 00:18:23.839 --> 00:18:26.140 Walker against Hyland for the Democratic nomination. 00:18:26.500 --> 00:18:29.220 And Hyland loses. But Red Mike still had one 00:18:29.220 --> 00:18:31.900 last strategic hustle left in him. He realizes 00:18:31.900 --> 00:18:34.220 he's out, but he strategically resigns from office 00:18:34.220 --> 00:18:38.069 on December 30, 1925, exactly one day before 00:18:38.069 --> 00:18:40.109 his term is officially supposed to end. Such 00:18:40.109 --> 00:18:42.630 a classic move. Why? To assure his eligibility 00:18:42.630 --> 00:18:47.509 for a $4 ,205 annual city pension. It was a purely 00:18:47.509 --> 00:18:50.950 pragmatic, survivalist move from a guy who never 00:18:50.950 --> 00:18:53.710 forgot what it felt like to have $3 .50 to his 00:18:53.710 --> 00:18:56.470 name. Even in defeat, he secured his financial 00:18:56.470 --> 00:18:59.190 future through a loophole. But Jimmy Walker couldn't 00:18:59.190 --> 00:19:02.470 resist one final ultimate burn. After becoming 00:19:02.470 --> 00:19:05.029 mayor, Walker actually appoints his defeated 00:19:05.029 --> 00:19:08.529 rival, Hyland, to be a judge on the Queen's Children's 00:19:08.529 --> 00:19:11.710 Court. When a journalist asked Walker why on 00:19:11.710 --> 00:19:14.109 earth he would appoint his political rival to 00:19:14.109 --> 00:19:16.829 a judgeship, Walker quipped, the children now 00:19:16.829 --> 00:19:19.710 can be tried by their peer. It's a brilliant 00:19:19.710 --> 00:19:23.210 cutting insult that highlights the absolute ruthlessness 00:19:23.210 --> 00:19:25.769 of New York City politics. So what does this 00:19:25.769 --> 00:19:28.750 all mean? We have a man who was endlessly mocked 00:19:28.750 --> 00:19:31.049 by the political and media elites. They called 00:19:31.049 --> 00:19:33.349 him a child. They laughed at his speeches. They 00:19:33.349 --> 00:19:36.809 ousted him from power. And yet the same man initiated 00:19:36.809 --> 00:19:39.190 massive infrastructure projects like the independent 00:19:39.190 --> 00:19:42.009 subway system. He fiercely championed the working 00:19:42.009 --> 00:19:44.230 poor against monopolies. He even had a mass. 00:19:44.400 --> 00:19:46.940 14 -mile boulevard and Staten Island Highland 00:19:46.940 --> 00:19:49.359 Boulevard named after him, despite his opponents 00:19:49.359 --> 00:19:51.940 protesting it all the way. It really illustrates 00:19:51.940 --> 00:19:54.279 the deep contradictions of a political legacy. 00:19:54.799 --> 00:19:58.099 He wasn't polished, but he was effective at navigating 00:19:58.099 --> 00:20:01.039 the brutal mechanics of the city. He understood 00:20:01.039 --> 00:20:03.700 the needs of the people who rode the trains because 00:20:03.700 --> 00:20:05.920 he used to drive them. It really is an incredible 00:20:05.920 --> 00:20:09.099 journey. From a kid reading a borrowed book on 00:20:09.099 --> 00:20:11.539 a mortgaged farm, shivering in the great blizzard 00:20:11.539 --> 00:20:14.640 of 1888 laying tracks, to sitting in the mayor's 00:20:14.640 --> 00:20:18.079 office at City Hall. He navigated the sharp elbows 00:20:18.079 --> 00:20:20.599 of Tammany Hall, fought the corporate trusts, 00:20:20.839 --> 00:20:23.680 and left a permanent physical mark on New York's 00:20:23.680 --> 00:20:26.019 transit map. This raises an important question, 00:20:26.140 --> 00:20:28.099 something for you to really mull over as we wrap 00:20:28.099 --> 00:20:31.180 up today. Hyland spent his entire life fighting 00:20:31.180 --> 00:20:33.759 the interests and the intellectual elites, fighting 00:20:33.759 --> 00:20:36.700 fiercely for the working class. Yet, history 00:20:36.700 --> 00:20:39.160 often remembers him through the jokes crafted 00:20:39.160 --> 00:20:41.519 by those very elites like Jimmy Walker and Robert 00:20:41.519 --> 00:20:44.220 Moses. Right. It makes you wonder, when we look 00:20:44.220 --> 00:20:46.480 back at history, are we seeing the truth of what 00:20:46.480 --> 00:20:48.880 a leader actually built, or are we just remembering 00:20:48.880 --> 00:20:51.140 the punchlines written by the people who defeated 00:20:51.140 --> 00:20:53.700 them? That is a phenomenal thought to end on 00:20:53.700 --> 00:20:55.980 and a perfect lens through which to view the 00:20:55.980 --> 00:20:57.880 stories we are told about historical figures. 00:20:58.279 --> 00:21:00.799 Thank you so much for joining us on this deep 00:21:00.799 --> 00:21:03.640 dive into the life of John Francis Hyland. We 00:21:03.640 --> 00:21:05.519 hope you take that question with you and that 00:21:05.519 --> 00:21:07.700 you keep exploring and questioning the history 00:21:07.700 --> 00:21:09.740 around you. We'll see you next time.