Rondo and Lester: Brothers in impending free agency

Rondo and Lester: Brothers in impending free agency
July 22, 2014, 2:15 pm
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We spend a lot of time these days talking about free agents, and by these days I mean right now  — in the world of twitter, the 24-hour news cycle. And as you know, the free agency discussion isn’t reserved for players who are actually free agents, but players who are about to be free agents, or are about-to-about-to-be free agents. Basically, from the moment an athlete signs a contract the world begins to wonder about what will happen when that contracts ends — and as time ticks away, that wonder slowly builds. Before long, whispers become screams and eventually all hell breaks loose.
 
That’s where we are with Jon Lester. And while the Rajon Rondo free agency discussion isn’t quite as advanced, it’s not that far behind. In the summer of 2014, I’d say that these are the two most talked about impending free agents in town and will be until they sign on somebody’s bottom line.
 
In the meantime, here are three thoughts on the pair:
 
1. MONEY MEN: Would you believe that Rondo’s made more money over his career than Lester has? Well, believe it. The Internet said so. And this blew my mind.
 
Yeah, I know the average NBA player ($5.15M) makes more than the average MLB player ($3.2M). But in this particular situation, I assumed that Lester: 30 years old — more than halfway through his ninth major league season — a four-time All Star — a two-time World Series champion — 3-0 with a 0.43 ERA over three World Series starts; 6-4 with a 2.11 ERA all-time in the postseason — plays in a league without a salary cap and for a team that’s among the top four in payroll every season . . .
 
Would have made more than Rondo: 28 years old — eight-year veteran — four-time All Star — NBA champion — categorized as a bargain the last four years — plays in a league with a salary cap that’s ranged between $53.1M and $63M during his career.
 
But that’s not that case. Instead, Lester will head into free agency (if the Sox let him get there) after nine seasons and roughly $43.5M in career earnings. Right now, through eight seasons, Rondo’s already made $47.8M and will head into free agency next summer, like Lester, after nine seasons, but with career earnings up over $60M.
 
Crazy, right? I don’t know how Jon Lester looks at himself in the mirror knowing he’s only made $43.5M over the last eight years.
 
2. MLTR: That’s “Most Likely to Return” — if we fast-forward to July 22, 2015, who’s more likely to still call Boston home?
 
Lester is the obvious answer, but I think it’s most likely that they’re both back. Lester, because he seems to genuinely want to return, and given his performance this year, the Sox will be forced to suck it up, and pay more than they originally intended. And Rondo because even if the trade rumors persist, Danny Ainge isn’t going to settle on a deal; he’s going to drive a hard bargain and it still takes two to tango. Can you name a team that needs a point guard, has the assets to get Rondo, enough remaining talent to still be competitive after getting Rondo, and dwells in a market that’s big enough to convince him to re-sign? I don’t know — maybe the Knicks? Indiana? Bottom line: There won’t be a lot of realistic suitors, and if they don’t trade Rondo, I believe the Celtics will find a way to re-sign him.
 
There won’t be too many realistic suitors for Jon Lester either, considering that he wants to stay in Boston and the Sox have some of the deepest pockets in baseball. BUT, if he tests the waters, the Yankees are lurking dangerously. They really need starting pitching, what with C.C. Sabathia all but toast, Masahiro Tanaka’s arm on the verge of snapping and the fact that Hiroki Kuroda is older than David Ortiz.
 
I repeat: THE YANKEES REALLY NEED STARTING PITCHING. And this isn’t a great free agent market for top-tier starting pitchers — there’s Lester, Max Scherzer and James Shields and that’s it. Not to mention, Lester is the only lefty in the crew, and after Sabathia, the Yankees don’t have another potential big time lefty in the system.
 
If the Yankees get desperate enough for Lester, that’s not good for Boston, or anyone else. Bidding against the Yankees in free agency is like bidding against John Henry at a monocle auction. You won’t win. You can’t win. If the Yankees break the bank with an offer (maybe seven years/$175M?) you couldn’t blame him for biting. And you couldn’t blame the Sox for bailing. But still, that means no more Jon Lester.
 
3. WHO’S THE MVP? The most valuable player. Is it more important that the Red Sox find a way to bring Lester back, or that the Celtics find away to make something happen around Rondo?
 
I’m sure the consensus is Lester, but for me, it comes down to how much the Sox are willing to spend — not just on Lester but in general.
 
They’ve already made a sizable investment in Dustin Pedroia — and it already looks like that might be a pain down the stretch. At some point in the next few years, they’ll need money to find a bat to replace David Ortiz, they’ll need money to find the bat that they need even with Ortiz. They’ll want to lock up Xander Bogaerts sooner rather than later — and Brock Holt deserves a raise at least in the neighborhood of what Mike Trout got.
 
But seriously, after the Dodgers bailed the Sox out in August 2012, Boston made a pledge not to go crazy with long term deals for 30-year-old-plus free agents. They broke that pledge with Dustin Pedroia, and that doesn’t look so sweet right now. It looks like they’re headed down that same road with Lester, and if this going to send them down that other same road again — where they’ll end up with too much money committed to older, underperforming players and not able to spend it elsewhere — then I’d let Lester walk. Maybe bring back Justin Masterson for less (even though he’s struggled this year) or other pitchers like him. Put some faith in the young arms on the farm, and then act accordingly — with the financial freedom to do so — if the situation calls for it.
 
In that case, I’d say it’s more essential for the Celtics to sign Rondo to a max-deal in the summer of 2015, let that max deal turn into another bargain when the NBA salary cap balloons in 2016, and build around a point guard (along with all the assets and picks the Celtics have) that’s still in his prime — as opposed to the Sox doing so with a starting pitcher already creeping up on the downside of his.
 
But that’s just me. I don’t have any real say in free agency. Just talk about it non-stop like everyone else.