This is a Generational Heist.....
Aug 31, 2026
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The Boston Red Sox may be in a position to conduct a generational heist against the
Pittsburgh Pirates and one of the best players in all of baseball. I'm here to break down how
Jeff Passan going on the Pat McAfee Show has started an absolutely never-ending saga of
conversation surrounding Paul Skeens and the likelihood of him being traded from the Pittsburgh
Pirates as early as this season. I'm here to break down how the Boston Red Sox should be
frontrunners if Skeens was available and what this would mean going forward for both organizations.
We'll break down all of that on this episode of Red Sox Digest but first before we get to
the news and information please do remember to subscribe to the channel as nearly 90% of you
guys watching this video are not currently subscribed. We do appreciate all the love and
support so thank you guys but now let's get to it and break down if there's really a chance of
Paul Skeens landing in Boston. Now Paul Skeens up to this point in his two-year career has been
simply phenomenal and there's no way around that. Last year it didn't seem like he was
it seemed like he was still in college based off the numbers he was putting up in Pittsburgh
absolutely dominant on the mound and it was kind of obvious he came out of LSU and from the start
all the way until the finish he was simply gross and there's really no way around it and up to
this point in the year he is once again gross and it doesn't matter if he's pitching against the
Phillies the Diamondbacks it doesn't matter he's going to compete he's going to be performing at a
very high level regardless of the team he is facing off against and up to this point in the year as a
fan of baseball if you have not witnessed Paul Skeens yet you're missing out because again like
I mentioned earlier the Phillies the Dodgers it doesn't matter the Diamondbacks he's going to go
out on that mound and despite not having a whole lot of run support from the Pittsburgh Pirates team
he's going to go out there and absolutely shove and he has done that a lot this year based off
his baseball spot you can tell he's pretty damn good when it comes to the overall percentiles
ranking amongst other starting pitchers in the MLB ranking in the top percentiles of fastball
being low expected batting average expected blow up things like the barrel percentage as well as
Paul Skeens is absolutely dominating and it's no surprise if you turn on the baseball game
and you actually watch him log six seven even eight innings of work
there is no surprise why the Pittsburgh Pirates last year called him up as early as they did
and gave him the keys to flat out dominate for all of last year and it seems like he's
going to dominate for the next 10 plus years in the MLB now the question is going to be
is it going to be for the Pittsburgh Pirates well seems like Jeff Passon doesn't believe so
and Jeff Passon also went on Pat McAfee and he had a bunch of conversations about the game of
baseball where Paul Skeens inevitably came up because obviously McAfee and the rest of the
crew on the McAfee show are dominantly from Pittsburgh and they have this conversation
about Pittsburgh sports how they would they love the idea that Pittsburgh sports are going to be
good and again they're not this Pittsburgh Pirates are not very good at baseball the
offensive production that they are getting is at the bottom of the barrel duo now if you look at
their starting rotation and the pieces that they have available currently with the fill pieces on
the rise like Jared Jones and Bubba Chandler as well as Paul Skeens they might have a very very
good three-headed monster in that starting rotation but outside of that are they going to
be able to be competitive most likely not you have Andrew McCutcheon being one of the better
offensive players on the Pittsburgh Pirates he's 40 41 years old he's been in the game of baseball
for as long as I've been alive he he's cannot be your cornerstone to your offense at this point in
his career don't get me wrong veteran leadership overall leadership in the sense of around the
clubhouse as well as leading by example on the diamond Andrew McCutcheon is probably one of the
top guys you would want on your roster but to be an everyday starter and to be a substantial piece
to your actual organization in the sense of offensive production I'm not sure if that's
really the route the Pirates should be going right now in the sense of probably resetting
looking at going and looking for younger pieces to reset their franchise so Paul Skeens will want
to stay in Pittsburgh and want to continue that that career in Pittsburgh now it shouldn't be
but this is where the pass and pull really comes from the fact that the Pirates organization has
been the way it has been up to this point the fact that Paul Skeen has been so damn good up to this
point and the Pirates have him under control for five more seasons before he reaches free agency
now the reason that is so important so impactful is because if the Pirates decide to hold on to
and Paul Skeens continues to produce at the level which he has and up to this point in his career
which again is only two years a year and a half later he's going to demand so much money in free
agency that the Pittsburgh Pirates physically might not be able to spend and pay all of the
money directly to him because it's one individual asset you guys don't know I'm not sure if I have
I am not going to have it up I apologize but the total roster value of the Pittsburgh Pirates
right now is 89 and contain 89 million dollars that's not a lot like the Dodgers have two
players that are worth a billion and they have 89 million dollars total on their entire loss
Paul Skeens is going to get more than that like every two years he's going to get more than 89
like Bregman right now for the Red Sox is getting 40 a year Paul Skeens is going to demand so much
money and these are this is off the sports track again these are the filtered by starting pitcher
so you do not have to try to filter in different names stuff like that just look at the overall
value of these contracts and then you look at the AAV obviously Yamamoto got is the highest paid
325 million I apologize his AAV is 27 million just for this one player now am I saying Paul
Skeens is going to get 27 to 30 million a year no I'm not saying that yet but there is a chance
that a bidder goes out there and gives him all the money possible because again if he does make it in
five years two free agencies and it's like it doesn't play out the way Vladimir Guerrero did
they went out and they paid him all the money he wanted regardless of the signing bonus size
regardless of the AAV regardless of the total years they were smart they said F it use all
the money you want back up the brake truck right to his back door and unload it because if we let
this wait and Vladimir Guerrero touches the open market and he can allow a bidding war to commence
amongst Boston, New York, LA, Toronto, Cleveland all of these teams that were going to be in on
Vladimir Guerrero Jr. his price would have tripled just like Juan Soto if the Yankees or if a team
would have came out before he went to free it would have been the Yankees if here's 550 million
dollars with 350 million dollar bonus there's a good chance they could probably land Soto before
he gets to the free agency market and maybe maybe it is a bit steeper because Soto
and his agent are apt they understand the value they understand the bidding war
process and really what that is going to cause and the effect of that but
you have to get ahead of this if you're the pirate if you allow schemes to hit the open market
he's going to cause a bidding war and you have no chance of re-signing him not only because
you haven't done anything to improve your offensive or the offensive side of your offense
in this organization and outside of Jared Jones and Bubba Chandler and Paul Schemes again Chandler
is a has a little bit ways to go before he's an MLB starter but obviously Jared Jones has been
in and off of the injury report really hasn't been all that consistent Schemes has really been the
lone guy for the entire organization field like that has been a model of consistency and someone
that is a bright point for this organization and because of that should he want to get out of
Pittsburgh should he he's an ultra competitor we know he wants to win we saw it at LSU we've seen
it in the early stages of his MLB career for the Pirates and now he's signed up for WBC because he
wants to be on a competitive stage with other elite level players if the Pirates don't go out
there and offer him a substantial number they haven't offered anyone in a hundred years to take
care of him for the rest of his career and just try to overwhelm him with the amount of money
they're going to give him there's no way in no doubt in my mind he doesn't hit free agency in
the next five years if not traded beforehand if the Pirates are smart and he's going to get paid
a king's ransom because of the overall bidding value that is going to happen now a few things
have to break down overall the starting rotation as of now for the Red Sox four guys Garrett Croce,
Giolito, Bale, and Dobbins and that looks the way it does because of the IL looking this way
Buehler, Crawford, Fitch, Howell, Murphy, and Sandoval all are still on the IL either still
on the IL or displaced on the IL to be interesting to see when all these guys return but because of
the amount of players on the IL you can question the depth of the Red Sox starting rotation right
now obviously the bullpen looked good yesterday against the New York Mets but how far is the
four-man rotation really going to take us until these guys return Buehler should be back pretty
soon Crawford and Fitch should both be back pretty soon as well Sandoval and Howell again are going
to miss a little bit more time until their return and this is just an interesting concept the idea
that teams could be on the move there's going to be a lot of big name teams in the market for him
and the idea of to reset the Pittsburgh Pirates franchise now they haven't had the greatest
franchise success overall so the idea that it could be a discounted price because well
they're just not running their organization correctly is a possibility now would I bet on it
absolutely not but I would also would not give up both Roman Anthony and Marcelo Meier in a package
together for one and Paul Sweeney yes Paul Sweeney is Paul Sweeney but to reset and give up two
players that could be a part of this Red Sox organization not only for the next 10 years but
possibly even the next 15 to 20 I think is too steep of a number for the Red Sox to give up in
order to go out and get someone like Paul Sweeney who's one Tommy John injury away from missing at
least a year and a half and then full rehabbing and possibly coming back to not be the same pitcher
they once traded for I think this is going to be a very interesting dilemma for the Pittsburgh
Pirates because well he he maintains so much value now the last thing we're going to close out
with is this and this is something that we've really already said just in different ways we're
just going to use the exact quote from Jeff Passant on the Pat McAfee show rather so this is in the
midst of his conversation with McAfee discussing the Paul Sweeney's idea and really why Sweeney
shouldn't want to sign with the Pittsburgh Pirates and why the Pirates should look to trade him so
what incentive does Paul Sweeney have to extend with the Pirates when the Pirates haven't shown
the willingness from either Bob Nutting all the way down the ability to bring in guys who are
going to make this team better the Pirates haven't shown that they are worthy of a Paul Sweeney's
extension at this point again that is a direct quote from Jeff Passant on or from the Pat McAfee
show this is a screenshot from where they're discussing it and it's he's really he's right
he's 100 right the Pirates haven't really done anything to improve this roster in any dramatic
fashion in order to win some games behind Paul Sweeney. Paul Sweeney won eight innings just
his last start I believe it was three days ago against the Philadelphia Phillies who are a very
credible baseball team and they lost one to nothing the the Pirates lost one to nothing
to the Phillies Sweeney went eight innings he gave up one run and they lost he's dominant and
they can't there's no help there offensively imagine this kid in Boston oh my god Duran,
Devers, Bregman, Willier, Abreu the run support would be astronomical it's like when Garrett
Posey gets run support just coming from the right-handed side I love this idea and honestly
if you want to start packaging a few a few of these prospects without packaging one and two
together I'm more than okay with having this conversation here's a way we can not give up
Hunter Dobbins as well I think we call Pittsburgh just ask hey are you guys actually thinking about
this are you is this something serious I like he's probably going to walk in five years would you
like to trade him now for a lot of value and reset your franchise I just call and find out
you know just play phone tag for a little bit and see what the Pirates are actually thinking
on this entire idea because this could be a generational hype for the Boston Pirates
I'll see you guys on the next one thank you for watching

