Jon Lester has signed a six year, $155 million deal with the Chicago Cubs, putting an end to a couple days of interminable, laser-specific coverage and setting the tone for the pitching free agent market — and that’s just fine. The Orioles were not, nor were they ever going to be, big players for Jon Lester, and this outcome takes him out of the AL East for the rest of his productive career.
What this means, though, is that the one big stumbling block to the Boston Red Sox making waves in the pitching trade market has now been removed — and that means the Orioles should probably get busy themselves: Philadelphia’s Cole Hamels might be on his way to the American League East.
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The Boston media has been insisting for a few days now that the Red Sox have the pieces to send back the other way to make a Cole Hamels trade work — I agree in theory, but I disagree with the assertion a number of analysts and Boston fans have made that the Phillies should take back secondary to tertiary prospects like Eduardo Rodriguez (who I had no specific hopes for when he was in the Orioles org) or guys like Matt Barnes or one of the lesser infielder prospects like Garin Cecchini or Deven Marrero. I think from Philadelphia’s perspective, talks to acquire Hamels should begin with either Mookie Betts or Blake Swihart on the table, with a heavy bias towards Betts, and I think that idea is completely unacceptable in Boston right now because the Betts hype train is catastrophically out of control.
That leaves an opening for the Orioles to involve themselves in the mix, and make a deal for a top of the rotation arm that can change the developing balance of power for 2015 while also providing a mainstay in the rotation for years to come. And I don’t think the Orioles should be anywhere near as shy about dealing a top prospect for Hamels the way the Red Sox were over the past week or so — because with Jon Lester off the market, Boston’s willingness to make a deal has probably gone up.
The dossier on Hamels: he’s entering his age-31 season having thrown 1064.2 IP of 3.00 ERA (129 ERA+) baseball over the past 5 years, with 202.4 IP of 2.46 ERA (151 ERA+) baseball. He’s got a clean bill of health, pitching at least 180 innings in every season since his first in Philadelphia, when he wasn’t called up until May. He strikes out almost four times as many guys as he walks, and he’s a consistent player who is good with the media and has basically the same ERA in the postseason as he does in the regular season (3.09 ERA in 81.2 IP). The big ding for the Orioles is that because Hamels is a good pitcher, he is paid like one: he will make $23.5 million a year for the next four years, with the final year of his deal being a team option for $20 million unless he pitches 400 innings in 2017-18, 200 of those innings are pitched in 2018, and he doesn’t end the season on the disabled list for an elbow/shoulder injury, in which case his 2019 option vests at $24 million. It has a $6 million buyout. That’s about in line with the yearly salaries of the game’s top pitchers — the guys slightly less otherworldly than Clayton Kershaw, a couple million a year fewer than Lester himself. It’ll cover him from age 31 to 35-36. That is the contract risk.
Any fan or analyst thinking that the Phillies absolutely have to unload Hamels’s contract at any price forgets that Philadelphia spends and budgets like a big market team. The idea of an Astros rebuild, or even a Cubs rebuild, is foreign to them. Ideally, they’d like to be competitive again in 2016 — 2017 at latest — and Cole Hamels still has value to a team with that window. And any idea that the Phillies would be throwing in significant money along with Hamels in a trade is out of step with reality.
It’s my firm belief that this Orioles team’s main window is this year and next year — the 2015-2016 offseason not only sees a number of key Orioles like Wieters and Davis hitting free agency, but a wave of key contributors like Tillman, Britton, Gonzalez, and even Flaherty hitting their Arb 2 year, which is when the big raises start to happen (Machado won’t be far behind, hitting Arb 1). So there’s going to be payroll squeeze by 2017, which Baltimore might already be planning for by walking away from big commitments like Nelson Cruz and Nick Markakis. Hamels in his early 30s is very likely to be a more valuable contributor than any of the above named players in this paragraph with the possible exception of Machado (assuming no more knee problems), is a far better win-now investment than re-signing Markakis would have been, and is only moderately more expensive. If the Orioles can clear a bit more space by trading Ubaldo Jimenez in a straight contract-dump, there should be no problems with adding Hamels’ deal and still keeping a balanced payroll — and if the O’s properly build around their core along with Hamels, they can extend their window even longer.
Which leaves the $100 million question: what’s an acceptable package to get this deal done, and done quickly while the Red Sox are hemming and hawing about how much they love their prospects? My proposal is SP Dylan Bundy, SP Miguel Gonzalez, IF Ryan Flaherty, and a minor leaguer of Philadelphia’s choice not named Harvey, Walker, or Alvarez. Though if they really wanted Alvarez for whatever reason, I wouldn’t let it be a dealbreaker.
There’s only three realistic centerpieces for this deal: Bundy, Kevin Gausman, and Hunter Harvey. Gausman is the one I suspect Philadelphia would prefer — he had a promising, if flawed, 2014, a whole lot of upside, and while he still needs to go deeper into games and refine his command, I have my suspicions that a lot of his problems would be cleared up by having continuity and comfort in his role with the team instead of being a pawn in Duquette’s endless roster fiddling. The Phillies would likely prefer Bundy to Harvey, and given that Harvey’s 2014 ended with him being shut down with elbow pain, Philadelphia will perhaps be understandably skittish making him the centerpiece of this deal. Bundy has his own injury concerns, but he’s on the other side of Tommy John — his 2014 wasn’t stellar, but it was also essentially rehab.
Trading Bundy could end up costing Baltimore an ace, but my faith in Baltimore’s ability to develop starting pitching in-house vanished at some point late last decade and I’ve seen no reason to come back to the fold as of yet. Besides, Bundy’s best pitch is a cutter — a pitch that this organization has a bizarre disdain for. That disdain cost them one possible ace already in Jake Arrieta, perhaps, but it’s likely just as true that if Arrieta remained in Baltimore he never would have had even one season as good as last year’s performance for the Cubs. The same might be true of Bundy. Hamels, on the other hand, is a finished product making top dollar — he should be essentially immune to any developmental problems, because he’s already long since developed.
Miguel Gonzalez is in there mainly because I think it’d be cool to have both Miguels Gonzalez in the majors in the same organization; you can replace him with Bud Norris or even TJ MacFarland if you feel. The idea is to trade from Baltimore’s back of the rotation surplus to make a spot for Hamels and give the Phillies a guy to replace him with on the roster. If he has a hot three months and Philadelphia can flip him at the deadline, even better for them. Dealing Gonzalez (or Norris) and Flaherty also lessens some of the arbitration crunch hitting the club after next season. The Orioles system falls off fairly severely after the top 5 or 6 players; giving Philadelphia one of the lower-ranked, lower-ceiling guys in the system — perhaps another pitcher, someone who profiles more for relief — should help seal the deal.
Baltimore is never going to beat out a suitor like Boston with quantity of prospects; if they want Hamels in orange and black, they’ll need to offer upside that Boston can’t — or won’t — match. Bundy provides that upside, and he’s one of three high upside young arms the Orioles have in their organization right now — an odd position of strength for them, at the moment. They should capitalize and see if they can turn that into one of the more consistent pitchers in baseball. Cole Hamels in front of the Baltimore defense could win himself a Cy Young.
But do I expect him to? Nah. Trading for Hamels isn’t this front office’s style — Marlon Byrd is much more Baltimore’s speed, which is why it’s unsurprising to hear that talks between the two clubs have mainly been focused on him and not the real prize. That is what it is, and it’s understandable risk avoidance. But Baltimore has a chance to make a real impact these next two seasons, and Cole Hamels is a guy that could help them do that. It’s just a question of whether or not the Orioles want to pay the price.

Jonathan is a contributing writer for VICE Sports. His work has previously appeared in Sports on Earth, Baseball Prospectus, The Classical, and ESPN’s SweetSpot Network. Born in central Maryland, Bernhardt currently lives in the New York metropolitan area.
