Did the Cubs truly miss out on free-agent catcher Russell Martin when the Toronto Blue Jays got him for five years at $82 million? Is it really a sure win for the Cubs if they land pitcher Jon Lester, even if they get him for last week’s reported offer of six years, $138 million?

You think front-office bosses Theo Epstein and Jed Hoyer know the answers to those questions?

If it looks as though they’re wading carefully into the deep end of the market this winter — even with cash-stuffed wallets for the first time in four offseasons — it’s probably for good reason:

Maybe they’re not very good at big-ticket free agency. And they know it.

Whether that says more about the Cubs’ leadership tandem or the risks inherent in the process can be debated. But there’s little debate when it comes to their spotty track record of free-agent spending that includes $230 million in swings and misses on Julio Lugo, Carl Crawford and Edwin Jackson in two cities over the last decade.

‘‘I think I’ve been better at drafting and developing, and smaller trades, than big free agents,’’ team president Epstein said. ‘‘But I think that’s fairly aligned with the industry.’’

To be sure, recent MLB free-agent classes include plenty of other deals that already look like clunkers, including a $155 million pitcher (Masahiro Tanaka) who suffered a serious elbow injury 20 starts into the contract and a $75 million outfielder (B.J. Upton) whose five-year contract looks at least as bad as Jackson’s four-year deal.

In fact, the Cubs look brilliant —  or lucky — for finishing second to the New York Yankees for Tanaka a year ago (they made a strong six-year, $120 million offer).

But Epstein and general manager Hoyer’s history of free-agent spending with big budgets in Boston was no better than the often-criticized Jim Hendry regime in Chicago, when the Cubs had one of the National League’s top payroll budgets.

And as they continue their pursuit of Lester, promising what would be the second nine-figure deal in franchise history — a year after the first expired — they’re treading into the area of team-building where they have proven perhaps least effective.

Huge risks come with all big free-agent contracts. But in Crawford, for example, Epstein’s Red Sox missed in evaluating a personality who thrived in small-market Tampa Bay but didn’t fit well with the constant buzz and hyper-scrutiny of Boston.

Halfway into Jackson’s four-year deal, nothing about his performance has lived up to a $52 million price tag for a player who never got a multi-year extension with any of his other seven teams and had a losing record for the 98-win Washington Nationals the year before the Cubs signed him.

The Cubs’ first choice that winter — Anibal Sanchez, who would have cost significantly more — led the American League in ERA in 2013 but suffered a series of injuries this year and didn’t make a start after Aug. 8.

‘‘It doesn’t add trepidation or anxiety,’’ Hoyer said, ‘‘but those times when you spend money in free agency and it doesn’t work out, there’s definitely an element of wisdom that you acquire.’’

If only frankincense and myrrh were U.S. currency.

Epstein’s front offices — and Hoyer’s for two years in San Diego — have fared much better finding value in short-term, low-risk free agents such as David Ortiz, Mike Timlin, Bill Mueller, Scott Feldman, Jason Hammel and Carlos Villanueva.

But they’ll almost certainly have to think, and spend, much bigger to create the winner they envision in Chicago, if only to acquire enough elite pitching.

‘‘I think you have to just go in knowing that the odds are stacked against you in free agency,’’ Epstein said, ‘‘but that’s still an important part of building a winning team.’’

So would you trust these guys to spend your money?

Japanese free agent Daisuke Matsuzaka cost Epstein’s Red Sox more than $101 million, including a posting fee, for six years, and the Red Sox got a 2007 title out his early success. But they also got four years worth of injury and ineffectiveness on the back end.

Was the World Series title worth nine figures? Or did dead money on two-thirds of the deal make the signing a bust?

Even Hoyer’s small-market Padres, coming off a 90-win 2010 season, missed big on a two-year, $11.5 million deal for four-time Gold Glove winner Orlando Hudson as they tried to shore up the middle infield of a potential contender. Hudson followed with his worst season and was released in May 2012 by Hoyer’s successor.

‘‘We spend all our time trying to get younger and trying to get more talented,’’ Hoyer said, ‘‘and with free agency, it’s oftentimes players in their 30s.’’

But everybody faces the same risk, he said.

‘‘We went aggressively into free agency going into the 2004 season with [$20.75 million closer] Keith Foulke and [low-risk deals for] Mike Timlin and Kevin Millar and David Ortiz, and we won the World Series,’’ Epstein said of Boston’s historic curse-buster. ‘‘And we went aggressively into the free-agent market going into the 2007 season and signed [$70 million] J.D. Drew and Daisuke Matsuzaka, and we won the World Series.

‘‘That said, there have been contracts we’ve signed that toward the end of those deals resulted in a lot of dead money. And I’m not going to walk away from that. That’s certainly true. But you have to have an organization that can withstand that, or else you shouldn’t be signing those contracts in the first place.’’

Epstein’s willingness to consider spending big now obviously says something about where he believes three years of organizational changes and prospect-gathering have taken the Cubs. It also indicates the economic heights he hopes will be achieved in a few years with a new local-TV deal.

But can the Cubs win big enough up front with an elite player for them to be able to live with dead money on the back end of a long-term deal?

And are they good enough at the calculus of free agency to minimize the dead money in any case?

‘‘Free agency is not for the faint of heart,’’ Epstein said.


Cubs executives Theo Epstein and Jed Hoyer, who have been heavily involved in big free-agent negotiations this winter, have not often fared well with big-ticket signings. Here are the biggest free-agent deals by Epstein and/or Hoyer (with the Red Sox and Cubs) and how they graded out.

Pos., Player, age Contract Signed Grade

OF Carl Crawford, 29 7y/$142m Dec. 2010 F

4-time All-Star w/ Rays struggled in big market, traded 8/28/2012

RHP Daisuke Matsuzaka, 26 6y/$103.1m* Dec. 2006  B-

Japanese star: 33 Ws in ’07-08, won W.S. game, injuries derailed last 4 yrs.

RHP John Lackey, 31 5y/$82.5m  Dec. 2009 C-

Beer-and-chicken ringleader salvaged passing grade w/ 3-1, 2.77 Oct. ’13

OF J.D. Drew, 31 5y/$70m   Feb. 2007 B

Oft-criticized deal proved market value for 4 yrs., included ’07 title

RHP Edwin Jackson, 29 4y/$52m Jan. 2013  F

Former All-Star has been league’s worst starter since deal

SS Edgar Renteria, 28   4y/$40m   Dec. 2004    D

Dumped for a prospect after offensive dip, defensive woes and flat October

SS Julio Lugo, 31    4y/$36m   Dec. 2006    F

Steep offensive decline upon signing; dumped in ’09 deadline trade

RHP Keith Foulke, 31   3y/$20.75m Dec. 2003    B-

Big 2004, including curse-busting title; injuries spoiled final 2 years

Note: List includes only multiyear deals for major-league players from outside the organization.

*-Includes $51.1 million posting fee