Stretch Your Knowledge with Surprise Guest Jeopardy James | Cubs Trivia, Episode 2

– [Michael] What’s up Cubs fans? I’m Mike Bolling and we’re here for
another edition of “Stretch Your Knowledge.” We’re looking for the most knowledgeable
Cubs fan to take on our resident expert, Gary Pressy, see if they can win this,
Kris Bryant signed baseball. This is a three round trivia contest
featuring you, Cubs fans, and our resident Cubs trivia expert/organist,
the one and only, Gary Pressy. The rules are simple. Round one consists of a knockout question,
one question of medium difficulty to advance to round two. You answer correctly and you’re in. Round two will be a lightning round and
the contestant with the most correct answers will advance to face our expert
Gary Pressy, in the final round. Round three is a one on one showdown with
Gary Pressy. Let’s see if these Cubs fans can take him
down. Round one starts right now. All right, first round question. How many World Series rings does Jon
Lester Have? – [Man 1] Jon Lester.
– [Man 2] Two. – That’s incorrect.
He has three. He won in 2007, 2013,
and then with us in 2016. – Okay.
– Jon Lester. – [Laura] If I get this wrong, am I done? – That is correct. – Jon Lester. – [Woman 1] Two. – That is incorrect. – Three?
– Yes, it is three. – Jon Lester.
One. – That is incorrect.
He’s got three. – Three? – He won two with the Red Sox and one with
the Cubs. – Okay.
– Oh my goodness. It’s Jeopardy James.
We got a ringer here. How’s it going, man?
I’m Mike . We’re doing “Stretch Your Knowledge.” It’s our trivia game show.
You want to participate? – [James] Of course.
– Let’s do it. First question, James. How many World Series rings does
Jon Lester have? – Ahh okay, so let’s see. He would have had one won in 2007 with the
Red Sox, 2016 with the Cubs. Ahh, let’s see. And yeah, he would have been with Boston
in 2013 also. So, three? – Three is correct.
Wow. I feel like this is going to be too easy
for you. How many World Series rings does Jon
Lester Have? – [Carson] Ooh . Three. – That is correct. – Shoot. I was going to say three, so three. – That is correct. How many World Series rings does
Jon Lester have? – [Woman 2] Four? – That’s incorrect. He has three. That’s…that’s closer than a lot of people
have gotten, though. – Thank you. – [Woman 3] Oh, man. – I’m not as blonde as I look. – How many World Series rings does
Jon Lester have? – [Carolyn] Three? – That’s correct. – Yaay. – That was the fastest answer we’ve had
today. – [Luke] Three. – That’s correct.
See? How many World Series rings does
Jon Lester have? – [Woman 4] Two?
Two. – [Woman 3] Two. – [Woman 6] How many did he have with
Boston? – I think he only won one.
– I’m going with two. – Two.
– Two. – Two is incorrect.
– Oh, three. – The Correct answer was three.
– Ooh. – Come on. Two out of three?
Like, come on. – Okay.
Oh, well. – Hey, but you’re a champ, though. James, Laura, Carson, Luke, and Carolyn,
Move on to round two, the lighting round. Okay, round two.
So our lightning round. One question, multiple answers. From 1990 to 2000, name as many Cubs all
stars as you can, without getting one wrong. If you get one wrong, you’re done. Ready? – Let’s start easy. Uh, Ryne Sandberg, for sure would have
made it. Uh, let’s see. Sammy Sosa.
Uh, let’s see. What a, the day, the dark times,
Mark Grace had to make a team here or there. I want to say Steve Trachsel was an all
star once back when they had to have one representative per team. Andre Dawson made it at some point in the
90s, I’m sure. More difficult now.
– There’s a catcher in there. – A catcher.
No. Uh, Rick Wilkins would have to be the
catcher, I think, or no? No, I’m out.
Ah. – I was thinking of Joe Girardi. But… Ah, wow, okay. I forgot about him. – Yeah, but I think that’s pretty good. All right, from 1990 to 2000. – Okay. – Name as many Cubs all stars as you can. – Oh wait, from 1990 to 2000? – Yes. – Oh gosh. I’m going to get this wrong. Was that Sammy Sosa era? – He is one. – Okay.
It’s the only one I know. – That’s it?
You’re just going to stop at one? – I don’t know them.
Let me, let me think. Let me think.
Let me think. – What if I did this? – Oh yes, Ryne Sandberg. – All right, two. – Okay. – You got any more? – [Man 3] First baseman. – First baseman? – [inaudible 00:04:37].
– Shoot. – Leftie. – That’s too many clues. That’s too many clues. – And I’m still not playing. – Thank you for participating. All right, so from 1990 to 2000,
how many Cubs All Stars Can you name? – Kris Bryant and- – Wait, wait, wait. – Okay. – From 1990 to 2000? – 2000. – All right, reset. – Greg Maddux. – That’s one. – Fergie Jenkins. – That is incorrect. You had Sammy Sosa, had Ryne Sandberg,
Andre Dawson. From 1990 to 2000, name as many Cubs all
stars as you can. – Ryne Sandberg. – There’s one. – Mark Grace.
Sammy Sosa. Maddux.
– Okay. – That’s all I got.
– You got four. From 1990 to 2000, name as many cubs all
stars as you can. – Uh, Anthony Rizzo. – Wait, wait, wait.
Stop, wait, let’s back up. – Okay.
– From 1990 to 2000. – Oh, 1990, I’m sorry I wasn’t paying
attention. Lester?
Yes. – 1990 to 2000.
– All right, I’m done. – That’s incorrect.
– I’m done. – Thank you for playing.
– I got one right. – Let’s take a look at our leaderboard
after round two. With five correct answers,
it looks like Jeopardy James is moving on to face our famed organist,
Gary Pressy in the final round. All right, we’re here at the final round
of “Stretch Your Knowledge,” legend versus legend, Jeopardy James versus
Gary Pressy. And for the final round question. Fergie Jenkins had the most career
strikeouts as a member of the Cubs. How many batters did he fan,
while pitching for the Cubs? You can write down your answers. ♪ music ♪ All right, you want to reveal at the same
time? – All right. – All right, here we go. Three, two, one… – Oh, no, I didn’t answer in the form of a question. – So looks like Gary is our winner. You came up against the expert,
an expert versus expert. The answer was 2038. Well, Gary is our winner,
still undefeated. But Jeopardy James, thank you so much for
coming and hanging out. We had a blast here with you today. – Thanks for having me, Michael. – We want to give a huge thanks to all of
our participants including Jeopardy James. We still need the best Cubs fan,
the most knowledgeable fan to beat our expert, Gary Pressy.
Will it be you? ♪ music ♪


  1. Nathan Bryan

    September 12, 2019 at 3:50 pm

    I have a new video in the works about the Cubs

  2. 吹上光之

    September 12, 2019 at 3:54 pm


  3. Kerri Doll

    September 12, 2019 at 4:09 pm

    What are all of the answers for the second question? (That was before my time as a Cubs fan.)

  4. Michael Reilly

    September 12, 2019 at 5:28 pm

    Who is Jeffrey James?

  5. Gabe Murrell

    September 12, 2019 at 5:41 pm

    go cubbies

  6. Ronald Rhinehart

    September 12, 2019 at 6:38 pm

    You can sure tell who the bandwagon fans were

  7. Derrick Parkinson

    September 12, 2019 at 7:33 pm

    Weeding out the bandwagons

  8. Michael Biancorosso

    September 12, 2019 at 7:45 pm

    The bandwagons are strong in this one

  9. gocubs22 .

    September 12, 2019 at 7:45 pm

    I'm confused, how did they just run into James Holzhauer?

  10. Manuel Ramos

    September 12, 2019 at 9:34 pm

    Don't mind me, I'm just Ryan Sandberg, HOF'r & perennial All-Star 2cd baseman. Can I introduce you to my friend Mark Grace, he had the most hits in the 90's.🐻🐻⚾️

  11. DONUTMAN #2

    September 12, 2019 at 9:37 pm

    Cubs are the best

  12. El Steve-O Radio™

    September 12, 2019 at 9:40 pm

    Man…I'm a lifelong Chicago Cubs fan since the first grade, and I would've past this with flying colors!

    I actually began becoming a Cubs fan in 1990, due to the once WGN Superstation airing Cubs games almost on the daily, nationally.

    And I'm from deep South, Texas, near Corpus, Christi, where they no longer broadcast games nationally for sometime now, unless MLBN or ESPN happens to broadcast the games.

    But I still have my ways to watch my Cubs play live.

    This makes me even more proud to know that I'm a "True" fan of the Cubbies, knowing their history, more so than most Chicago Natives! 😊

    Cubs up, 3-0, against San Diego, Mid 6th.

    🏆⚾️"Go Cubs Go!"⚾️🏆

  13. Tarman

    September 13, 2019 at 1:18 am

    why did Gary win when he was also wrong? he put 2319 but the answer was 2038?

  14. Preston Jones

    September 13, 2019 at 6:40 am

    I gotchu

  15. Norbert Daniels

    September 13, 2019 at 5:59 pm

    Really sad all the high horses we have around here from some of us cubs fans. Knowing historical knowledge about a sport/team/player is not something that defines a "true" fan vs a bandwagoner. Most of these people weren't even born back then, and a lot just don't study MLB history. Chill out and enjoy the game.

  16. Chase Miller

    September 14, 2019 at 3:34 am

    Go cardinals

  17. cubs컵스

    September 14, 2019 at 7:11 pm

    I am South korea cubs fan
    I like cubs. My life cubs No.1 Thank you cubs~

  18. SonicBooom96

    September 16, 2019 at 5:15 pm

    How do you get the first one wrong?
    The all star one Is a little difficult and I wasnt alive to know how many SO fergie jenkins had as a cub.

  19. RWB Team

    September 17, 2019 at 6:41 pm

    If you can't guess any of those correctly you have an issue and not a true Cub fan.

  20. Mike Praznowski

    September 17, 2019 at 7:03 pm

    Please let me know the next time you guys do this. I’ll take down the legend.

  21. Ryan Varner

    September 19, 2019 at 5:13 am

    This was painful. Lol

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