Exploring Kevin O'Leary's Crazy Watch Collection

Kevin O'Leary stopped by to show me some of the crazy watches in his collection and to talk watches with me. Mr. Wonderful discussed his collecting journey, watches as investments, as well as the watch market as a whole. I also shared some watches with the Shark Tank star, including the brand new Fleming Series One and some pieces from European Watch Company.
Check out Kevin O'Leary's Channel: @kevinoleary
Check out WonderCare Watch Insurance: wondercare.com/
Check out European Watch Company @europeanwatchco: www.europeanwatch.com/
Get your watch news and watch buying guides: www.wristenthusiast.com/
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00:00 Introduction and Wrist Check
01:50 Kevin's Watch Collecting Journey
04:00 Change in Collecting Over the Years
06:22 Does Kevin Ever Sell His Watches?
06:52 The Craziest Offer For a Watch
07:04 The Viral 1/1 AP Royal Oak with Ruby Bezel
07:45 Getting a Custom Luxury Watch
09:16 Keeping Collecting Exciting
12:45 Watches Kevin Can't Get
14:21 Kevin and Teddy Baldassarre
16:59 WonderCare Watch Insurance
19:14 Watches as Investments and the Future of the Watch Market
21:17 Thoughts on F.P. Journe
24:18 The Red Strap and Any Watches that Kevin Won't Put On It
27:48 Thoughts on Richard Mille
30:23 Flashy and Trashy Watches
31:34 Kevin's Next Iced Out Watch
33:15 Kissing His watches
34:50 Thoughts on Celebrity Watch Collections
38:02 Advice on Building a Watch Collection
40:40 Thoughts on Watches & Wonders
45:11 Fleming Series 1
47:04 Watches from European Watch Company

[@DanyalIssoufalyHKokar]

I loved the fact that even though they are here to present MrO'Leary's watch collection, the interviewer is asking questions about the man, not his possessions

[@nickgee7291]

Kevin is so relatable as far as mentality on watch collecting, he's really down to earth in that way. His collection is an another level sure, but his mentality is relatable to allot of watch collectors. He has great dialogue

[@danielduncan2883]

Loved the interviewer. Best questions O'Leary has had to answer. Great insight not heard before. Well done. Just subscribed. O'Leary does inspire me to go harder collecting

[@alexderavedissian9169]

Always been partial to O'Leary because of his ties to Cyprus ... his insight into his watch collection, and the status that comes with that collection, was very interesting. Great pod.

[@MazER644]

Great interview! Both of you are very knowledgeable and your enthusiasm is amazing. As a young collector, I hope to be in the same place as you two many years from now!

[@wristenthusiast]

I’m sure you will be! Watches is a lifelong hobby. I’m always learning!

[@Tnapvrvideo]

Bravo on the never sell mindset. I very much appreciate that level of true passion to collect and own a magnificent piece of art for your entire lifetime. Well Done!

[@TimG--]

Great content mate 🥃

[@wristenthusiast]

Thank you!

[@JoeyJiggles]

Some good questions that I haven’t heard from any other watch channel. Nice work.

[@robingranger444]

I like Kevin, hes down to warth and a family man, hes also into wines, olive oils, cars,real estate, and watches to name just a few; and of course hes Canadian...that giant country with 90% of its population living less than 100km away from its southern border.

[@snapascrew]

Tim Robinson interviewing Mr Wonderful? Awesome! I’m not worried about any of this!!!!!!

[@alberokadaa8354]

Super cool interview! So much info for us watch enthusiasts!

[@wristenthusiast]

Glad you enjoyed it!

[@BradHanssen]

Really great video and interview, Craig! This is random, but I actually came across you years ago in the Home Gym Community Facebook group and admired your apartment living room setup! I was just getting into watches at that time but didn't know much about them. Kevin's comments were pretty accurate in that I started with a Hamilton, then moved to a GS not long after. Funny how quickly it can escalate haha

[@wristenthusiast]

Thank you! Yes, I got really into the home gym setup back in the day. And I am still a fan of Hamilton. My Khaki Field Murph 38 is one of my favorites!

[@robin2thek]

I love this interview. its so nice when things are not rushed. Letting Kevin take his time. Also nice that Kevin asked you some questions. We also know who the real bosses on Shark tank are, the wardrobe staff :)

[@thierry1491]

Kevin you don’t like flippers which I totally agree with. What do you think about brands promoting flipping like Patek and Rolex?

[@user-gs5jw3er2i]

Awesome interview! 👏🏼👏🏼The AP with the rubies is my fave! ☺️

[@wristenthusiast]

It’s insane. Was crazy to see it in person!

[@dsamaridis]

I have to hand it to him: that F. P. Journe Tourbillion Remontoire with the red band is absolutely glorious!

[@Aleksilausti]

Great interview with lots of new insights from Kevin. I like your calm way of conducting an interview. Thanks for this treat 🙂

[@wristenthusiast]

Thank you! Which is your favorite watch we featured?

[@danchapman5944]

Delighted to hear about Kevin’s insurance product - much needed!!!

[@joshsteuterman2363]

Mr. O’Leary is a class act. I feel that he truly loves this. This is fun for him. And, it’s fun to listen to. Thanks for this interview.

[@wristenthusiast]

Thank you for watching! Glad you liked it!

[@robertp5123]

Nice interview with Kevin. I know you mentioned the Tantalum metal. Kevin, take a look at the Omega 25th Anniversary Seamaster (Tantalum) that came out a few years ago. This piece also has several other metals with the tantalum. Stunning timepiece that is under the radar.

[@Andy-ri1ns]

Great interview, and I love the channel. The Patek museum in Geneva only opened in 2001 so I call bullshit on that. O'Leary is a hypebeast collector and only got into it when the bubble commenced for purely monetary reasons.

[@marcelohendrix6139]

whether watches were passed from your grandfather or you got into it last year it doesnt matter. snobs like you make the hobby elitist and so shitty

[@michaelyohannesmy]

You are doing a fantastic job with your channel. I truly enjoy it. Keep going!

[@wristenthusiast]

Thank you so much for the kind words! Hopefully more good content to come!

[@20thcenturyboy85]

SPECTACULAR Collection!!! Mr. O'Leary has seriously expanded the entire mechanical wrist watch market over the past decade with all his video collaborations, and especially working with Teddy Baldassarre.

[@rapidenthusiasm-oc4go]

Kevin redeemed himself in this video after his recent Producer Michael video performance!

[@jimallen833]

Great interview guys! Watched it twice.

[@MCMXI1]

A facinating and unexpectedly rich interview that was so much more than just talking about a watch

[@wristenthusiast]

Thank you!

[@IvanGarcia-wf6yi]

Great interview! great questions

[@readmycomment3157]

Excellent interview

[@DavidTran23]

Enjoyed hearing Kevin’s stories

[@MrCparlak]

I love all watches he has. They are wonderful looking with red bands.

[@wristenthusiast]

But which is your favorite? I would say mine is either the AP with ruby bezel or the Journe vertical tourbillon. The Simon Brette is not bad at all either

[@MrCparlak]

Rolex Daytona with red band

[@nikkimiddlekillsday5161]

Out of all of Kevin's watches that I've seen him show on videos I'd have to say his GS Katana, Daytona Meteorite and definitely each if his F.Ps are my tops

[@mitchmatic8029]

Great video and interview.

[@drnick40]

Great video. Thank you very much. Wonderful pieces presented by true gentlemen.

[@wristenthusiast]

Glad you enjoyed it

[@avmelidor]

Enjoyed this

[@sinjinadams2862]

Fantastic video! I really enjoyed it.

[@wristenthusiast]

Glad to hear that!

[@brewwatchco]

Absolutely incredible collection!

[@gtv6chuck]

Great interview. Kevin is a very down to earth collector who has appreciation for all levels of watches and appears to have no elitist attitude regarding his watches. He simply enjoys them as an enthusiast.

[@wristenthusiast]

So true! Thanks for watching

[@jcmartinez7527]

Kevin O’Leary is such an incredible conversationalist. And you are a great interviewer! Well done.

[@wristenthusiast]

Thank you so much! I'm glad you enjoyed the conversation. What was the most interesting part to you?

[@jcmartinez7527]

@@wristenthusiastit was fascinating to hear how he develops relationships with all these brands. Just goes to show how charismatic he is and how passionate he is for watches.

[@nikkimiddlekillsday5161]

Also show how watch companies have practically become political parties.

[@BruceWaynex7]

great interview. interesting questions.

[@edwardholst5493]

Great interview. Can’t get enough interviews with Mr. Wonderful. So much knowledge and love his perspective. Rolex Daytona is the crown jewel for me.

[@wristenthusiast]

Thank you! Can never go wrong with a Daytona.

[@baxoutthebox5682]

Kevin really doesn’t know anything about watches aside from what they’re worth

[@liangliangsansan6231]

He did sell his watch, e.g. his 116500 panda Daytona with red band in the last auction season.

[@Whatisallthisfor949]

I love it when he says vertical but moved his hands along the horizontal axis 😂😅

[@zacharypalczynski8450]

Loves hearing himself talk

[@dustondaugherty4611]

Great interview!

[@wristenthusiast]

Thanks!

[@michaeldemarco899]

Kevin! What a wonderful guest! You should look into getting an RGM custom made by Roland in PA! You’ll love it

[@nikkimiddlekillsday5161]

I've seen some of those in books, they look insane

[@michaeldemarco899]

@@nikkimiddlekillsday5161 Yes they are wonderful pieces I’m actually getting a piece unique

[@SAMZIRRA]

That blue one! Wow

[@gregash4387]

That JLC is a deadly gorgeous watch !!!!! So Beautiful….

[@breakupgoogle]

that 5231J-001 PP is so nice. I want the 5131/1P-001

[@Test-Tube-Baby-xo8xx]

A luxury watch to me is something like a Tissot but I'm thoroughly happy with that.

[@geekylizard]

OK Craig!!! Great interview.

[@wristenthusiast]

Thank you!

[@MacmillerMwema]

Amazing video, Amazing stories, Amazing watches

[@wristenthusiast]

Thank you so much!

[@CapnFlags]

If I like purple with a non-rubber band and a tasteful accompaniment of diamonds, what’s my top 5 watches? Note: I really love purple. Also love rose gold and would pick that or silver/platinum over yellow gold.

[@Patekcollector5205]

I love the AP

[@SoCalWatchReviews]

Great video 👏

[@sullivanbacerdo3244]

the Fleming case is made by Efteor SA, not Vacheron. Efteor has made cases for the Zeitwerk, for example

[@wristenthusiast]

Good catch. My mistake on that. Thanks for clarifying!

[@dielalex89]

Kevin gets a lot of love, and also a lot of hate from the watch community too… ok well, maybe not “hate” … but maybe some eye-rolling etc.. lol… but I give him the pass - I think he is definitely a watch guy.. sure, yes, you will hear him every now and then make a really goofy comment or say something that maybe other true “watch guys’ wouldn’t say -- but we also have to remember what level of status this guy is on -- of course he’s going to be a bit different I always enjoy seeing his videos.. or interviews like this, or with other KZbinrs and so on --- I feel like Kevin has been instrumental in getting luxury watches even more mainstream- and there is no denying it, that he truly loves this stuff and I think it’s just great - I would love to get to meet him and talk watches You did a great job with the interview - Im subscribed now!

[@georgen26]

collecting piece uniques is insane. FP Journe, heard some shadde about him, only time will tell ;)

[@TomasLjung-jj5dp]

Did you see kojak T S wearing a led digital watch in 70 s so many brands today nice interview keep the time must say Bravissimo ☆☆☆☆☆

[@andrisveiss3212]

What a great interview! I have the same disease (just a smaller wallet for now lol)

[@akhrormuminov7180]

Disclaimer.! No more tears were shed during the recording of this video.

[@nikolajjrgensen6538]

3 min in, already all good on Mr.NotSoWonderful :)

[@michaeldemarco899]

Sorry I liked this so much I’m commenting twice! Your from Boston? I’ve bought several pieces from European Watch Co. have you ever been to Paul Duggan? I have a good size collection now and my passion stetted when I was 16!!

[@wristenthusiast]

Yes I am! I have lived in NYC for a while now but am back to Boston very often!

[@AbesamisM]

i dont even really like watches but that shark tank AP is amazing to look at.

[@Derceto360]

Very Good! 👏

[@TseringNamgyalLama]

Solid interview! This is first time independents got much needed exposure.

[@wristenthusiast]

Glad you liked it!

[@SteveFWatches]

Happy to see his collection grow further into independents now

[@gfeast4518]

He’s really going off his rocker, from not knowing much not too long ago now wearing 6 watches a day? Nutty

[@dhimitritheodhori7187]

Kevin is top man

[@TravisCannata]

I gotta respect the double wristing.

[@KamillGran-ch5sb]

The business in Abu Dhabi is Abu Dhabi Dhu… good time..

[@vatsalsanwaria537]

"I'm not a bought guy" Kevin, FTX is calling you.

[@avmelidor]

Kevin has impeccable taste

[@kevinmccalister8197]

He loves himself so damn much.

[@MacmillerMwema]

Who doesn't?

[@JohnnyJohnJon83]

@@MacmillerMwemaKeanu Reeves

[@NaviNavi-1uu8tg]

That’s why he is Mr.Wonderful 😂

[@wristenthusiast]

Which of Mr. Wonderful's watches is your favorite?

[@MacmillerMwema]

Lange & sonhe

[@gregorydelost3324]

The ones he didn’t use SBFs blood money to buy

[@kunvh829]

Fleming doing big things!

[@adamgc73]

I have a $100 clear swatch skeleton i constantly get remarks about it 😊

[@paulosullivan3991]

Top class

[@gentlewolf]

If Kevin's pocket square ever goes white, ALL his watches will get red faced, be purple with rage, have a case of the blues, become green with envy, and get yellow fever. Orange I correct?

[@F3PIZZA]

Diamonds can only cut diamonds. Diamonds go hard asf.

[@JacobNozicka]

I really want to know what's up with the red.

[@jeejkee6471]

Honestly, not many people have the experience and possibilities as Kevin does. I think it would be a shame if some watch maker wouldn’t work with him and create something new in the watch industry.

[@MDSkai]

I imagine half the time Kevin needs to know the time, he looks at his wrist and realizes he’s too wealthy to have watches that actually make it easy enough and just does a rich-guy laugh to himself

[@SteveFWatches]

😂😂😂😂 yep so many GMTs would resolve this. But he likes what he likes 🤷🏻‍♂️

[@benjaminfrank_]

My issue with Kevin and his watch collection is that in EVERY single watch video he has to mention “shark tank” 😂😂

[@jimm0802]

Great interview. What happens to a collection like Kevin’s when eventually passes away.? We all pass away, just curious about unique collections when flipping is so taboo

[@Yorkiepoocharlie]

Likely will go to auction just like many do. Brando, Schumacher, Newman.

[@SpookyConcepts]

The MB&F Bulldog is the holy grail

[@MrGrazzhoppa]

Piece unique maybe but holy grail, that’s a hell no..

[@andrewvaughan5686]

Great interview, incredible watches, but i gotta agree with those that say wearing 2 watches is way too over the top.

[@nikkimiddlekillsday5161]

Not if you travel between two different time zones and have business there

[@andrewvaughan5686]

@@nikkimiddlekillsday5161 lol sure

[@baxoutthebox5682]

@@nikkimiddlekillsday5161as if he doesn’t have a GMT lol

[@naillonhutnick]

Amei todas as bolsas lindas e de muito bom gosto.Parabens #mamacoo 😘😘

[@DJPhantomRage]

I can't even wish to have anything in his collection, let alone be able to afford anything. I do understand the never letting go of a item I have some extremely valuable pocket watches from family that have been passed down to me. Those will stay with me, just like the few watches that have beem gifted to me. Even though they aren't as valuable.

[@franklucente3517]

Is he confusing “The Three Horsemen” with “The Holy Trinity?” 😂 When did Rolex assume the Vacheron mantel??

[@rem9011]

He means the big 3 obviously, biggest and hardest to get. Vacheron is leagues behind in terms of popularity, demand and spotlight.

[@kelvin.008]

Most on Red bands, quite a joke isn't it 😂

[@christianmatthes8802]

Who is the guy in UAE that know every caliber and had such a big collection?

[@JeDxDeVu]

Hope he doesn’t cry again

[@PhilipPaul-vw7hu]

Me sitting here with not a single dollar in my bank account thinking, "oh yeah I could probably get one of those one day" XD

[@FJames]

Really good video, Kevin is always best on longer form interviews

[@donjuan150]

Great interview...but maybe it is time to move on from the Red??

[@nathandallas4878]

Because continuity isn't a thing for television like nobody changes their outfits all season

[@BabyJesus66]

Agreed. I always feel like hes the only one who cares that much what color his watch strap is. If they were worried about continuity wouldnt changing the watches at all be a problem?

[@cliftonmcmullen7167]

Must be nice to only want piece unique’s when I’m trying to get a 36mm Date Just, two tone 😂

[@simonrushton4639]

What’s shark tank?

[@leciaman]

I am confused why would the color of the watch band matter when you are on Shark Tank

[@TheZibil]

how do we get ourselves to trust grey market dealers?

[@slydermartin6008]

Great conversation. Great Watches.

[@wristenthusiast]

It was fun to film!

[@Mr.LDSIII]

Napoleon Complex egomaniac

[@ricardocampos3383]

cope

[@swiftusmaximus5651]

6 watch changes in a day, LMAO.

[@Spazik86]

Well everone has to have some way to spend money. How do you spend millions of dollars? You need to find some "stupid" money sink, some people collect cars, some people paintings, he is collecting watches.. :)

[@jordandavies68]

Kevin is the only person who can convolute an answer which has no response to the question asked. What do you think will be released? Watches and wonders is a gathering of people who enjoy watches. Shame I thought it was a Barbie doll conference. Incredibly smart bloke, very successful and wealthy but his knowledge on watches is mediocre at best.

[@ryanjofre]

He’s an incredible businessman, a good family man and he’s an insufferable douchebag braggart.🤮 He’s a rank Watch novice at best! He talks like he’s a pro but he’s not fooling anyone with his B.S. Allot of the companies he deals with in Switzerland probably laugh at him when he leaves the building. Teddy Baldassarre who looks like he just finished puberty has real Watch knowledge, wisdom and something Kevin will never have…..HUMILITY🙏. If business went really bad for him he’d start flipping watches in a New York minute. Watching Kevin make a fool of himself with Teddy is entertaining though. I wish you and your hideous signature red watch straps the best Kevin. 🤮

[@BabyJesus66]

You haven't listened to any Donald Trump interview? 😂

[@jordandavies68]

@@BabyJesus66 trump shits all over Biden. Period😂