Since Manny we have signed Lugo, Renteria, Drew, Crawford, Hanley, Pablo, Dice K, Lackey, even Price to some extent to 5+ year, big money contracts. When are we going to learn? We won in 13 with Gomes and Shane on reasonable contracts.
The idea that there are abundant free agent options at "reasonable contracts" is a myth.
Here are recent FA starting pitchers and position players signed between two and four years. Contracts not underwater are in bold. (It's a snow day.)
2014 offseason
Arroyo (2/23), Baker (2/3.7), Beltran (3/45), Bloomquist (2/5.8), Byrd (2/16),
Colon (2/20),
Rajai Davis (2/10), DeJesus (2/10.5), Diaz (4/8), Feldman (3/30), Garza (4/50),
Granderson (4/60), Guerrero (4/28), Hudson (2/23),
Hughes (3/24), Infante (4/30), Jimenez (4/50), Garrett Jones (2/7.5),
Kazmir (2/22), Lincecum (2/35), Loney (3/21), McLouth (2/10.75), Jose Molina (2/4.5),
Morneau (2/12.5), David Murphy (2/12),
Napoli (2/32), Navarro (2/8), Nolasco (4/49), Pelfrey (2/11), Peralta (4/53), Ruiz (3/26), Brendan Ryan (2/5), Saltalamacchia (3/21), Schumaker (2/5), Sweeney (2/3.5),
Uribe (2/15),
Vargas (4/32)
2015 offseason
Butler (3/30), Melky Cabrera (3/42),
Cruz (4/58), Cuddyer (2/21), Descalso (2/3.6),
Hammel (2/20), Hardy (3/40),
Headley (4/52),
Hundley (2/6.25), Kang (4/11), LaRoche (2/25), Liriano (3/39),
Lowrie (4/29), Markakis (4/44), Victor Martinez (4/68), McCarthy (4/48), Medlen (2/8.5),
Morales (2/17), Morse (2/16), Peavy (2/24),
Hanley Ramirez (4/88), David Ross (2/5),
Santana (4/55), Shields (4/75), Toscano (4/7.5),
Volquez (2/20)
2016 offseason
Asdrubal Cabrera (2/18.5), Cespedes (3/75 with opt out),
Estrada (2/26),
Flowers (2/5.3), Gallardo (2/22), Gordon (4/72),
Happ (3/36), Jaso (2/8), Kazmir (3/48),
Kendrick (2/20), Kim (2/7), Lackey (2/32),
Murphy (3/37), Park (4/12), Pelfrey (2/16), Brayan Pena (2/5), Pennington (2/3.75), Span (3/31),
Young (2/13), Zobrist (4/56)
2017 offseason
Butera (2/3.8),
Castro (3/24.5), Cespedes (4/110), Desmond (5/70), Encarnacion (3/60), Hammel (2/16),
Hill (3/48),
Joyce (2/11), Dae Ho Lee (4/12.9), Mathis (2/4), Morales (3/33),
Morton (2/14), Moss (2/12),
Nova (3/26), Pearce (2/12.5), Ramos (2/12.5),
Reddick (4/52), Sean Rodriguez (2/11.5),
Thames (3/16),
Turner (4/64), Valbuena (2/15), Volquez (2/22), Wieters (2/21), Travis Wood (2/12)
The only guys with positive value the Sox had openings for were Colon, Davis, Granderson, Hughes, Kazmir, Morneau, Uribe, and Vargas in 2014; Cruz, Headley, Santana, and Volquez in 2015; Estrada and Happ in 2016; and Castro, Morton, Thames, and Turner in 2017. The rest of those guys are blocked.
The full sum of revisionist history positional player improvements is not large. Rajai Davis would have been better than our fourth outfielders in 2014-15. Juan Uribe would have been better than Holt/Bogaerts and Sandoval in 2014-15, though reports were he was comfortable in Los Angeles. Justin Morneau may have been marginally better than Napoli (dubious because of the Coors factor) in 14-15. Coors again, but maybe Nick Hundley's a better bet than Swihart in 2015-16, though it also would have blocked development time. Curtis Granderson might have been better than who he'd have replaced in our outfield from 2014-17, but he's a bad Fenway fit at the plate and couldn't cover right field like Betts can. Maybe Tyler Flowers would have looked good over our catchers. Howie Kendrick would have been better as a fourth outfielder than Chris Young (if he'd have signed for that). Headley was a better option than Sandoval from 15-17, but he may have been comfortable in New York after playing there the back half of 2014. Jason Castro had a better year at the plate than Vazquez and Leon last year, but I'll take Vaz over the next two. Finally, Nelson Cruz may have been better than Hanley as a LF in 2015, a 1B in 2016, and a DH in 2017.
Some short deals for starting pitching can be decent value. It's still plenty volatile, but 12 of 32 starting pitchers to sign between two and four years have been worth the money so far. Hill and Nova might fall off that list, but Morton's legacy is sealed.
Happ at 3/$36M looks better than Price at 7/$217M. We would have been better off signing Uribe, Lowrie, or Headley than Sandoval. Seattle struck gold with Nelson Cruz. That deal was widely panned at the time and we didn't have a DH spot open for him, but maybe he would not have been a defensive nightmare on the same journey Hanley took.